Root, Inc. - Proxy Solicitation & Information Statement 2026

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

(Amendment No. )

Filed by the Registrant ☒

Filed by a Party other than the Registrant ☐

Check the appropriate box:

☐ Preliminary Proxy Statement

☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

☒ Definitive Proxy Statement

☐ Definitive Additional Materials

☐ Soliciting Material Pursuant to § 240.14a-12

ROOT, INC.

(Name of Registrant as Specified in its Charter)

(Name of Person(s) Filing Proxy Statement, if Other Than the Registrant)

Payment of Filing Fee (Check all boxes that apply):

☒ No fee required

☐ Fee paid previously with preliminary materials

☐ Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11

Root, Inc.

80 E. Rich Street, Suite 500

Columbus, Ohio 43215

(866) 980-9431

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

To Be Held On June 3, 2026

To the Stockholders of Root, Inc.:

On behalf of our board of directors, it is our pleasure to cordially invite you to attend the 2026 Annual Meeting of

Stockholders (the “Annual Meeting”) of Root, Inc., a Delaware corporation (the “Company”). The Annual Meeting

will be held virtually, via live webcast at www.virtualshareholdermeeting.com/ROOT2026 , originating from

Columbus, Ohio, on Wednesday , June 3, 2026 , at 11:00 a.m. Eastern Daylight Time. We believe hosting a virtual

meeting enables participation by more of our stockholders, while lowering the cost of conducting the meeting.

Stockholders attending the virtual meeting may participate and vote online during the virtual meeting. We encourage

you to attend online and participate. We recommend that you log in a few minutes before 11:00 a.m. Eastern

Daylight Time, on June 3, 2026 , to ensure you are logged in when the Annual Meeting starts.

The Annual Meeting will be held for the following purposes:

1. To elect three Class III directors, Lawrence Hilsheimer, Alexander Timm and Douglas Ulman ,

each to hold office until our Annual Meeting of Stockholders in 2029 ;

2. To ratify the selection by the audit, risk and finance committee of our board of directors of

Deloitte & Touche LLP as our independent registered public accounting firm for the fiscal year

ending December 31, 2026 ;

3. To approve, on an advisory basis, our named executive officer compensation;

4. To approve an amendment to the Company’s Amended and Restated Certificate of Incorporation,

as amended, to allow for exculpation of certain officers; and

5. To conduct any other business properly brought before the Annual Meeting.

These items of business are more fully described in the Proxy Statement accompanying this Notice.

The record date for the Annual Meeting is April 6, 2026 . Only stockholders of record at the close of business on that

date may vote at the Annual Meeting or any adjournment thereof.

By Order of the Board of Directors,

Jodi E. Baker

Chief Legal Officer and Secretary

Columbus, Ohio

April 24, 2026

You are cordially invited to attend the Annual Meeting. Whether or not you expect to attend the Annual Meeting, PLEASE VOTE YOUR SHARES. As an alternative to voting online at the Annual Meeting, you may vote your shares in advance of the Annual Meeting through the internet, by telephone or, if you receive a paper proxy card in the mail, by mailing the completed proxy card. Voting instructions are provided in the Notice of Internet Availability of Proxy Materials or, if you receive a paper proxy card by mail, the instructions are printed on your proxy card. Even if you have voted by proxy, you may still vote online if you attend the Annual Meeting. Please note, however, that if your shares are held of record by a broker, bank or other agent and you wish to vote at the Annual Meeting, you must follow the instructions from such organization.

TABLE OF CONTENTS

Page

QUESTIONS AND ANSWERS ABOUT THESE PROXY MATERIALS AND VOTING ..............................	2
PROPOSAL 1 - ELECTION OF DIRECTORS ...................................................................................................	9
INFORMATION REGARDING DIRECTOR NOMINEES AND CURRENT DIRECTORS ...........................	10
INFORMATION REGARDING THE BOARD OF DIRECTORS AND CORPORATE GOVERNANCE ......	14
NON-EMPLOYEE DIRECTOR COMPENSATION ..........................................................................................	26
PROPOSAL 2 - RATIFICATION OF OUR SELECTION OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM ..........................................................................................................................................	28
EXECUTIVE OFFICERS .....................................................................................................................................	29
EXECUTIVE COMPENSATION ........................................................................................................................	30
PROPOSAL 3 - APPROVAL, ON AN ADVISORY BASIS, OF OUR NAMED EXECUTIVE OFFICER COMPENSATION ................................................................................................................................................	58
PROPOSAL 4 - APPROVAL OF AN AMENDMENT TO THE COMPANY’S AMENDED AND RESTATED CERTIFICATE OF INCORPORATION TO ALLOW FOR EXCULPATION OF CERTAIN OFFICERS ............................................................................................................................................................	59
SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT .........................	61
TRANSACTIONS WITH RELATED PERSONS ...............................................................................................	64
DELINQUENT SECTION 16(a) REPORTS ........................................................................................................	65
HOUSEHOLDING OF PROXY MATERIALS ...................................................................................................	65
OTHER MATTERS ..............................................................................................................................................	66
APPENDIX A .......................................................................................................................................................	A- 1

Root, Inc.

80 E. Rich Street, Suite 500

Columbus, Ohio 43215

(866) 980-9431

PROXY STATEMENT

FOR THE 2026 ANNUAL MEETING OF STOCKHOLDERS

To Be Held on June 3, 2026 at 11:00 a.m. Eastern Daylight Time

Our board of directors is soliciting your proxy to vote at the 2026 Annual Meeting of Stockholders (the “Annual

Meeting”) of Root, Inc., a Delaware corporation, to be held virtually, via live webcast at

www.virtualshareholdermeeting.com/ROOT2026 , originating from Columbus, Ohio, on Wednesday , June 3, 2026 ,

at 11:00 a.m. Eastern Daylight Time and any adjournment or postponement thereof. We believe hosting a virtual

meeting enables participation by more of our stockholders, while lowering the cost of conducting the meeting.

Stockholders attending the virtual meeting may participate and vote online during the virtual meeting.

For the Annual Meeting, we have elected to furnish our proxy materials, including this proxy statement (the “Proxy

Statement”) and our Annual Report on Form 10-K for the fiscal year ended December 31, 2025 (the “Annual

Report”), to our stockholders primarily via the internet. On or about April 24, 2026 , we expect to mail to our

stockholders a Notice of Internet Availability of Proxy Materials (the “Notice”) that contains notice of the Annual

Meeting and instructions on how to access our proxy materials on the internet, how to vote at the Annual Meeting

and how to request printed copies of the proxy materials. Stockholders may request to receive all future materials in

printed form by mail or by email by following the instructions contained in the Notice. A stockholder’s election to

receive proxy materials by mail or email will remain in effect until revoked. We encourage stockholders to take

advantage of the availability of the proxy materials on the internet to help reduce the environmental impact and cost

of our Annual Meeting.

Only stockholders of record at the close of business on April 6, 2026 (the “Record Date”) will be entitled to vote at

the Annual Meeting. On the Record Date, there were 14,015,900 shares of Class A common stock, 1,806,236 shares

of Class B common stock and 14,053,096 shares of Series A Convertible Preferred Stock (the “Series A preferred

stock”) outstanding and entitled to vote. Each holder of Class A common stock will have the right to one vote

per share of Class A common stock and each holder of Class B common stock will have the right to 10 votes

per share of Class B common stock . The holder of the Series A preferred stock is entitled to vote with the

holders of Class A common stock and will have the right to one vote per each share of Class A common stock

into which the Series A preferred stock is convertible, or 780,727 votes. The holders of shares of Class A

common stock, Class B common stock and Series A preferred stock will vote together as a single class on all matters

submitted to a vote at the Annual Meeting. A list of stockholders entitled to vote at the Annual Meeting will be

available for examination for 10 days before the Annual Meeting at our address above. If you would like to view the

list, please contact our Secretary at [email protected] to schedule an appointment. The stockholder list will also

be available online during the Annual Meeting. For instructions on how to attend the Annual Meeting, please see the

instructions at www.virtualshareholdermeeting.com/ROOT2026 and on page 2 of this Proxy Statement. You will

not be able to attend the Annual Meeting in person.

In this Proxy Statement, we refer to Root, Inc. as “Root,” the “Company,” “we” or “us” and the board of directors of

Root as the, or our, “board of directors.” The Annual Report, which contains consolidated financial statements as of

and for the fiscal year ended December 31, 2025 , accompanies this Proxy Statement. You also may obtain a copy of

the Annual Report without charge by emailing [email protected].

QUESTIONS AND ANSWERS ABOUT THESE

PROXY MATERIALS AND VOTING

Why did I receive a notice regarding the availability of proxy materials on the internet?

Pursuant to rules adopted by the Securities and Exchange Commission (the “SEC”), we have elected to provide

access to our proxy materials over the internet. Accordingly, we have sent you the Notice because our board of

directors is soliciting your proxy to vote at the Annual Meeting, including at any adjournments or postponements

thereof. All stockholders will have the ability to access the proxy materials on the website referred to in the Notice

or to request a printed set of the proxy materials. Instructions on how to access the proxy materials over the internet

or to request a printed copy may be found in the Notice. We intend to mail the Notice on or about April 24, 2026 , to

all stockholders of record entitled to vote at the Annual Meeting.

Why are you holding a virtual Annual Meeting?

The Annual Meeting will be held solely in a virtual format, which will be conducted via a live webcast. We have

created and implemented the virtual format in order to facilitate stockholder attendance and participation by enabling

stockholders to participate from any location around the world, at no cost. However, you will bear any costs

associated with your internet access, such as usage charges from internet access providers and telephone companies.

A virtual Annual Meeting makes it possible for more stockholders (regardless of size, resources or physical location)

to have direct access to information more quickly, while saving Root and our stockholders time and money. We also

believe that the online tools we have selected will increase stockholder communication. For example, the virtual

format allows stockholders to communicate with us in advance of, and during, the Annual Meeting so they can ask

us questions.

Will I receive any other proxy materials by mail?

You will not receive any additional proxy materials via mail unless (1) you request a printed copy of the proxy

materials in accordance with the instructions set forth in the Notice or (2) we elect, in our discretion, to send you a

proxy card and a second Notice, which we may send after 10 calendar days have passed since our first mailing of the

Notice.

How do I attend, participate in and ask questions during the Annual Meeting?

We will be hosting the Annual Meeting via live webcast only. Any stockholder can attend the Annual Meeting live

online at www.virtualshareholdermeeting.com/ROOT2026 . The meeting will start at 11:00 a.m. Eastern Daylight

Time, on Wednesday , June 3, 2026 . Stockholders attending the Annual Meeting may participate and vote online

during the virtual meeting.

In order to enter the Annual Meeting, you will need the control number, which is included in the Notice or on your

proxy card if you are a stockholder of record of shares of Class A common stock, Class B common stock or Series A

preferred stock, or included with your voting instruction card and voting instructions received from your broker,

bank or other agent if you hold your shares in “street name.” Instructions on how to attend and participate are

available at www.virtualshareholdermeeting.com/ROOT2026 . We recommend that you log in a few minutes before

11:00 a.m. Eastern Daylight Time on June 3, 2026 to ensure you are logged in when the Annual Meeting starts. The

webcast will open 15 minutes before the start of the Annual Meeting.

If you would like to submit a question during the Annual Meeting, you may log in at

www.virtualshareholdermeeting.com/ROOT2026 using your control number, type your question into the “Ask a

Question” field and click “Submit.”

To help ensure that we have a productive and efficient meeting and in fairness to all stockholders in attendance, you

will also find posted our rules of conduct for the Annual Meeting when you log in prior to its start. These rules of

conduct will include the following guidelines:

• You may submit questions and comments electronically through the meeting portal during the Annual Meeting.

• Only stockholders of record as of the Record Date for the Annual Meeting and their proxy holders may submit

questions or comments.

• Please direct all questions to Alexander Timm, our Chief Executive Officer (“CEO”).

• Please include your name and affiliation, if any, when submitting a question or comment.

• Limit your remarks to one brief question or comment that is relevant to the Annual Meeting and/or our business.

• Questions may be grouped by topic by our management.

• Questions may also be ruled as out of order if they are, among other things, irrelevant to our business, related to

pending or threatened litigation, disorderly, repetitious of statements already made, or in furtherance of the

speaker’s own personal, political or business interests.

• Be respectful of your fellow stockholders and Annual Meeting participants.

• No audio or video recordings of the Annual Meeting are permitted.

What if I have technical difficulties or trouble accessing the Annual Meeting?

We will have a toll-free technical support “help line” ready to assist you with any technical difficulties you may

have accessing the Annual Meeting. If you encounter any difficulties accessing the Annual Meeting during the

check-in or meeting time, please call the technical support number that will be posted at

www.virtualshareholdermeeting.com/ROOT2026 . Technical support will be available starting 15 minutes before

11:00 a.m. Eastern Daylight Time on June 3, 2026 .

Who can vote at the Annual Meeting?

Only stockholders of record at the close of business on the Record Date, April 6, 2026 , will be entitled to vote at the

Annual Meeting. On the Record Date, there were 14,015,900 shares of Class A common stock and 1,806,236 shares

of Class B common stock. The holder of the outstanding shares of Series A preferred stock is entitled to 780,727

votes.

• Stockholder of Record: Shares Registered in Your Name . If, on the Record Date, your shares were registered

directly in your name with our transfer agent, Equiniti Trust Company, LLC , then you are a stockholder of

record. As a stockholder of record, you may vote online during the Annual Meeting or by proxy in advance.

Whether or not you plan to attend the Annual Meeting, we urge you to vote your shares by proxy in advance of

the Annual Meeting through the internet, by telephone or by completing and returning a printed proxy card that

you may request or that we may elect to deliver at a later time to ensure your vote is counted.

• Beneficial Owner: Shares Registered in the Name of a Broker or Bank . If, on the Record Date, your shares

were held not in your name, but rather in an account at a brokerage firm, bank or other similar organization,

then you are the beneficial owner of shares held in “street name” and the Notice is being forwarded to you by

that organization. The organization holding your account is considered to be the stockholder of record for

purposes of voting at the Annual Meeting. As a beneficial owner, you have the right to direct your broker, bank

or other agent regarding how to vote the shares in your account. You are also invited to attend the Annual

Meeting. However, since you are not the stockholder of record, you may vote your shares online during the

Annual Meeting only by following the instructions from such organization.

How many votes do I have?

Each holder of shares of our Class A common stock will have one vote per share of Class A common stock held as

of the Record Date and each holder of shares of our Class B common stock will have 10 votes per share of Class B

common stock held as of the Record Date. The holder of the Series A preferred stock is entitled to vote with the

holders of Class A common stock and will have the right to one vote per each share of Class A common stock into

which the Series A preferred stock is convertible, or 780,727 votes. The holders of the shares of our Class A

common stock, Class B common stock and Series A preferred stock will vote as a single class on all matters

described in this Proxy Statement for which your vote is being solicited.

What am I voting on?

There are four matters scheduled for a vote:

• Proposal 1: Election of three Class III directors, each to hold office until our annual meeting of stockholders in

2029 ;

• Proposal 2: Ratification of the selection by the audit, risk and finance committee of our board of directors of

Deloitte & Touche LLP as our independent registered public accounting firm for the fiscal year ending

December 31, 2026 ;

• Proposal 3: Approval, on an advisory basis, of our named executive officer compensation; and

• Proposal 4: Approval of an amendment to the Company’s Amended and Restated Certificate of Incorporation,

as amended, to allow for exculpation of certain officers.

What if another matter is properly brought before the Annual Meeting?

Our board of directors knows of no other matters that will be presented for consideration at the Annual Meeting. If

any other matters are properly brought before the Annual Meeting, it is the intention of the persons named in the

accompanying proxy to vote on those matters in accordance with their best judgment.

How do I vote?

• Stockholder of Record: Shares Registered in Your Name. If you are a stockholder of record, you may vote

(1) online during the Annual Meeting or (2) in advance of the Annual Meeting by proxy through the internet, by

telephone or by using a proxy card that you may request or that we may elect to deliver at a later time. Whether

or not you plan to attend the Annual Meeting, we urge you to vote by proxy to ensure your vote is counted. You

may still attend the Annual Meeting and vote online even if you have already voted by proxy.

• To vote online during the Annual Meeting, follow the instructions provided to join the Annual Meeting

at www.virtualshareholdermeeting.com/ROOT2026 , starting at 11:00 a.m. Eastern Daylight Time on

Wednesday , June 3, 2026 . The webcast will open 15 minutes before the start of the Annual Meeting.

• To vote in advance of the Annual Meeting through the internet, go to www.proxyvote.com to complete

an electronic proxy card. You will be asked to provide the control number from the Notice or the

printed proxy card. Your internet vote must be received by 11:59 p.m. Eastern Daylight Time on

Tuesday , June 2, 2026 , to be counted.

• To vote in advance of the Annual Meeting by telephone, dial 1-800-690-6903 using a touch-tone

phone and follow the recorded instructions. You will be asked to provide the control number from the

Notice or the printed proxy card. Your telephone vote must be received by 11:59 p.m. Eastern Daylight

Time on Tuesday , June 2, 2026 , to be counted.

• To vote in advance of the Annual Meeting using a printed proxy card, which you may request or we

may elect to deliver to you, simply complete, sign and date the proxy card and return it promptly in the

envelope provided. If you return your signed proxy card to us before the Annual Meeting, we will vote

your shares as you direct.

• Beneficial Owner: Shares Registered in the Name of Broker or Bank. If you are a beneficial owner of shares

registered in the name of your broker, bank or other agent, you should receive a Notice containing voting

instructions from that organization rather than from us. Simply follow the voting instructions in the Notice to

ensure that your vote is counted. To vote online during the Annual Meeting, you must follow the instructions

from your broker, bank or other agent.

Internet voting during the Annual Meeting and/or internet proxy voting in advance of the Annual Meeting allows you to vote your shares online, with procedures designed to ensure the authenticity and correctness of your vote instructions. Please be aware that you must bear any costs associated with your internet access.

Can I vote my shares by filling out and returning the Notice?

No. The Notice identifies the items to be voted on at the Annual Meeting, but you cannot vote by marking the

Notice and returning it. The Notice provides instructions on how to vote by proxy in advance of the Annual Meeting

through the internet, by telephone, using a printed proxy card or online during the Annual Meeting.

What does it mean if I receive more than one Notice?

If you receive more than one Notice, your shares may be registered in more than one name or in different accounts.

Please follow the voting instructions on the Notice to ensure that all of your shares are voted.

Can I change my vote after submitting my proxy?

• Stockholder of Record: Shares Registered in Your Name. If you are a stockholder of record, then yes, you can

revoke your proxy at any time before the final vote at the Annual Meeting. You may revoke your proxy in any

one of the following ways:

• Submit another properly completed proxy card with a later date.

• Grant a subsequent proxy by telephone or through the internet.

• Send a timely written notice that you are revoking your proxy to our Secretary via email at

[email protected].

• Attend the Annual Meeting by visiting www.virtualshareholdermeeting.com/ROOT2026 and vote

online during the meeting. Simply attending the Annual Meeting will not, by itself, revoke your proxy.

Even if you plan to attend the Annual Meeting, we recommend that you also submit your proxy or

voting instructions or vote in advance of the Annual Meeting by telephone or through the internet so

that your vote will be counted if you later decide not to attend the Annual Meeting.

Your most current proxy card or telephone or internet proxy is the one that is counted.

• Beneficial Owner: Shares Registered in the Name of Broker or Bank. If you are a beneficial owner and your

shares are held in “street name” by your broker, bank or other agent, you should follow the instructions

provided by your broker, bank or other agent.

If I am a stockholder of record and I do not vote, or if I return a proxy card or otherwise vote without giving

specific voting instructions, what happens?

If you are a stockholder of record and do not vote through the internet, by telephone, by completing the proxy card

that may be delivered to you or online during the Annual Meeting, your shares will not be voted.

If you return a signed and dated proxy card or otherwise vote without marking voting selections, your shares will be

voted in accordance with the recommendations of our board of directors: “ FOR ” the election of each of the three

nominees for director, “ FOR ” the ratification of the selection of Deloitte & Touche LLP as our independent

registered public accounting firm for the fiscal year ending December 31, 2026 , “ FOR ” the approval, on an advisory

basis, of our named executive officer compensation, and “ FOR ” the approval of an amendment to the Company’s

Amended and Restated Certificate of Incorporation, as amended, to allow for exculpation of certain officers . If any

other matter is properly presented at the Annual Meeting, your proxyholder (one of the individuals named on your

proxy card) will vote your shares using his or her best judgment.

If I am a beneficial owner of shares held in “street name” and I do not provide my broker, bank or other

agent with voting instructions, what happens?

If you are a beneficial owner and do not instruct your broker, bank or other agent how to vote your shares, the

question of whether your broker or nominee will still be able to vote your shares depends on whether, pursuant to

stock exchange rules, the particular proposal is deemed to be a “routine” matter. Brokers and nominees can use their

discretion to vote “uninstructed” shares with respect to matters that are considered to be “routine,” but not with

respect to “non-routine” matters. Under applicable rules and interpretations, “non-routine” matters are matters that

may substantially affect the rights or privileges of stockholders, such as mergers, stockholder proposals, elections of

directors (even if not contested), executive compensation and certain corporate governance proposals, even if

management supported. Accordingly, your broker or nominee may vote your shares on Proposal 2 without your

instructions. Your broker or nominee, however, may not vote your shares on Proposals 1, 3 or 4 without your

instructions. Such an event would result in a “broker non-vote” and these shares will not be counted as having been

voted on Proposals 1, 3 or 4. Please instruct your bank, broker or other agent to ensure that your vote will be

counted.

What are “broker non-votes”?

As discussed above, when a beneficial owner of shares held in “street name” does not give instructions to the broker

or nominee holding the shares as to how to vote on matters deemed to be “non-routine,” the broker or nominee

cannot vote the shares. These unvoted shares are counted as “broker non-votes.”

As a reminder, if you are a beneficial owner of shares held in “street name,” in order to ensure your shares are

voted in the way you would prefer, you must provide voting instructions to your broker, bank or other agent by

the deadline provided in the materials you receive from such organization.

How are votes counted?

Votes will be counted by the inspector of election appointed for the Annual Meeting, who will separately count, for

the proposal to elect directors, votes “ FOR ” or “ AGAINST ,” abstentions and broker non-votes; with respect to the

proposal to ratify the selection of Deloitte & Touche LLP as our independent registered public accounting firm for

the fiscal year ending December 31, 2026 , votes “ FOR ” or “ AGAINST ” and abstentions; with respect to the

proposal to approve, on an advisory basis, our named executive officer compensation, votes “ FOR ” or

“ AGAINST ,” abstentions and broker non-votes; and with respect to the proposal for approval of an amendment to

the Company’s Amended and Restated Certificate of Incorporation, as amended, to allow for exculpation of certain

officers, votes “ FOR ” or “ AGAINST ,” abstentions and broker non-votes.

How many votes are needed to approve each proposal?

The holders of the shares of our Class A common stock, Class B common stock and Series A preferred stock will

vote as a single class on all matters described in this Proxy Statement.

Proposal	Vote Required for Approval	Abstentions	Broker Non- Votes
1. Election of directors	Each of the three nominees must receive “ FOR ” votes from holders of a majority of shares cast. Any director nominee who does not receive a majority of the votes cast shall promptly tender a resignation to the nominating and governance committee, which will make a recommendation to the board of directors as to whether to accept or reject the resignation or take other action. The board of directors will, within 90 days following certification of the election results, publicly disclose its decision regarding the resignation and, if such resignation is rejected, the rationale behind the decision.	No effect	No effect
2. Ratification of the selection of Deloitte & Touche LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2026	Must receive “ FOR ” votes from the holders of a majority of shares present by virtual attendance or represented by proxy and entitled to vote on the matter.	Against	Not applicable
3. Approval, on an advisory basis, of our named executive officer compensation	Must receive “ FOR ” votes from the holders of a majority of shares present by virtual attendance or represented by proxy and entitled to vote on the matter. Although the advisory vote on this proposal is nonbinding, the board of directors and the compensation committee expect to consider the results of the vote when making executive compensation decisions.	Against	No effect
4. Approval of an amendment to the Company’s Amended and Restated Certificate of Incorporation, as amended, to allow for exculpation of certain officers	Must receive “ FOR ” votes from the holders of at least 66 2/3% of the shares outstanding and entitled to vote on the matter.	Against	Against

The holder of our Series A preferred stock has agreed to vote its shares of Series A preferred stock at the Annual

Meeting in support of Proposal 1 and in the same proportion as our unaffiliated stockholders with respect to all of

the other proposals. Our “unaffiliated stockholders” do not include any of our current officers and directors and any

other beneficial owner of more than 5.0% (determined on a fully diluted basis) of our outstanding common stock

(other than investors that are eligible to file a Schedule 13G with the SEC pursuant to Rule 13d-1(b) under the

Securities Exchange Act of 1934 (the “Exchange Act”)) and any affiliate of any of the foregoing persons.

What is the quorum requirement?

A quorum of stockholders is necessary to hold a valid meeting. A quorum will be present if stockholders holding at

least a majority of the voting power of the outstanding shares entitled to vote are present at the Annual Meeting by

virtual attendance or represented by proxy. On the Record Date, there were 14,015,900 shares of Class A common

stock and 1,806,236 shares of Class B common stock outstanding and entitled to vote. As of the Record Date, the

holder of the outstanding shares of Series A preferred stock is entitled to 780,727 votes.

Your shares will be counted towards the quorum only if you submit a valid proxy (or one is submitted on your

behalf by your broker, bank or other agent) or if you vote online during the Annual Meeting. Abstentions and broker

non-votes will be counted towards the quorum requirement. If there is no quorum, the holders of a majority of the

voting power of the shares present at the Annual Meeting by virtual attendance or represented by proxy may adjourn

the Annual Meeting to another date.

How can I find out the results of the voting at the Annual Meeting?

Preliminary voting results will be announced at the Annual Meeting. In addition, final voting results will be

published in a Current Report on Form 8-K that we expect to file within four business days after the Annual

Meeting. If final voting results are not available to us in time to file a Form 8-K within four business days after the

Annual Meeting, we intend to file a Form 8-K to publish preliminary results and, within four business days after the

final results are known to us, file an additional Form 8-K to publish the final results.

When are stockholder proposals due for next year’s annual meeting?

To be considered for inclusion in next year’s proxy materials pursuant to Rule 14a-8 under the Exchange Act, your

proposal must be submitted in writing by December 25, 2026 , to our Secretary at 80 E. Rich Street, Suite 500,

Columbus, Ohio 43215, Attention: Secretary. Rule 14a-8 and related guidance provide that certain stockholder

proposals may be excluded from a proxy statement. We will evaluate any stockholder proposal received and may

exclude such stockholder proposal if permitted in accordance with such rule and guidance.

Pursuant to our Amended and Restated Bylaws, if you wish to submit a proposal (including a director nomination) at

the annual meeting of stockholders to be held in 2027 (the “ 2027 Annual Meeting”) that is not to be included in next

year’s proxy materials, you must do so not later than the close of business on March 5, 2027 , nor earlier than the

close of business on February 3, 2027 . However, if the date of our 2027 Annual Meeting is held prior to May 4,

2027 or after July 3, 2027 , to be timely, notice by the stockholder must be received (A) not earlier than the close of

business on the 120th day prior to the 2027 Annual Meeting and (B) not later than the close of business on the later

of the 90th day prior to the 2027 Annual Meeting or, if later than the 90th day prior to the 2027 Annual Meeting, the

10th day following the day on which public announcement of the date of the 2027 Annual Meeting is first made.

You are also advised to review our Amended and Restated Bylaws, which contain additional requirements about

advance notice of stockholder proposals and director nominations. A stockholder who intends to solicit proxies in

support of director nominees other than the Company’s nominees must satisfy the foregoing requirements under our

Amended and Restated Bylaws, including providing the information required by Rule 14a-19 under the Exchange

Act. The requirements of such notice can be found in our Amended and Restated Bylaws, a copy of which is on our

website, at ir.joinroot.com .

Our proxy related to the 2027 Annual Meeting will give discretionary authority to the proxy holders to vote with

respect to all proposals submitted outside the process of Rule 14a-8 received by us after the date determined in

accordance with our Amended and Restated Bylaws.

Who is paying for this proxy solicitation?

We will pay for the cost of soliciting proxies. In addition to these proxy materials, our directors and employees may

also solicit proxies in person, by telephone or by other means of communication. Directors and employees will not

be paid additional compensation for soliciting proxies. We may reimburse brokers, banks and other agents for the

cost of forwarding proxy materials to beneficial owners.

PROPOSAL 1 - ELECTION OF DIRECTORS

Our board of directors currently consists of eight members and is divided into three classes. Each class consists, as

nearly as possible, of one-third of the total number of directors and each class has a three-year term. At each annual

meeting of stockholders, the successors to directors whose terms then expire will be elected to serve from the time of

election until the third annual meeting following the election.

Our directors are divided into the three classes as follows:

• Class III directors: Lawrence Hilsheimer, Alexander Timm and Douglas Ulman, whose terms will expire at the

Annual Meeting;

• Class I directors: Beth Birnbaum, Donna Dorsey and Julie Szudarek, whose terms will expire at the 2027

Annual Meeting; and

• Class II directors: Jerri DeVard and Nancy Kramer, whose terms will expire at the annual meeting of

stockholders to be held in 2028.

Any additional directorships resulting from an increase in the number of directors will be distributed among the

three classes so that, as nearly as possible, each class will consist of one-third of the directors. Vacancies on the

board of directors may be filled only by persons elected by a majority of the remaining directors. A director elected

by the board of directors to fill a vacancy in a class, including vacancies created by an increase in the number of

directors, shall serve for the remainder of the full term of that class and until the director’s successor is duly elected

and qualified. The division of our board of directors into three classes with staggered three-year terms may delay or

prevent a change of our management or a change in control of Root.

Messrs. Hilsheimer, Timm and Ulman have each been nominated for reelection to serve as a Class III

director. Each of Messrs. Hilsheimer, Timm and Ulman is currently a member of our board of directors and was

previously elected by the stockholders at the annual meeting of stockholders held in 2023. Each of these nominees

has agreed to stand for reelection at the Annual Meeting. Our management has no reason to believe that any

nominee will be unable to serve. If elected at the Annual Meeting, each of these nominees would serve until the

annual meeting of stockholders to be held in 2029 and until his successor has been duly elected, or if sooner, until

the director’s death, resignation or removal.

Our Amended and Restated Bylaws include a majority vote standard for uncontested director elections, which

requires that a nominee for director in an uncontested election receive a majority of the votes cast at a stockholder

meeting in order to be elected to the board of directors. Any director nominee who does not receive a majority of the

votes cast shall promptly tender a resignation to the nominating and governance committee, which will make a

recommendation to the board of directors as to whether to accept or reject the resignation or take other action. The

board of directors will, within 90 days following certification of the election results, publicly disclose its decision

regarding the resignation and, if such resignation is rejected, the rationale behind the decision. If any nominee

becomes unavailable for election as a result of an unexpected occurrence, shares that would have been voted for that

nominee may instead be voted for the election of a substitute nominee proposed by us.

Our nominating and governance committee seeks to assemble a board of directors that, as a whole, possesses the

appropriate balance of professional and industry knowledge, financial expertise and high-level management

experience necessary to oversee and direct our business. To that end, the nominating and governance committee has

identified and evaluated nominees in the broader context of the board of directors’ overall composition, with the

goal of recruiting members who complement and strengthen the skills of other members and who also exhibit

integrity, collegiality, sound business judgment and other qualities that the nominating and governance committee

views as critical to effective functioning of the board of directors. To provide a mix of experience and perspective on

the board of directors, the nominating and governance committee also takes into account diversity (including gender

identity, race, ethnicity, nationality, religion, disability, age and sexual orientation) and other factors that it deems

appropriate to maintain a balance of knowledge, experience, and capability on the board of directors. The

biographies below include information, as of the date of this Proxy Statement, regarding the specific and particular

experience, qualifications, attributes or skills of each director nominee that led the nominating and governance

committee to believe that that nominee should continue to serve on the board of directors. However, each of the

members of the nominating and governance committee may have a variety of reasons why a particular person would

be an appropriate nominee for the board of directors and these views may differ from the views of other members.

OUR BOARD OF DIRECTORS RECOMMENDS A VOTE “FOR”

EACH CLASS III DIRECTOR NOMINEE NAMED ABOVE.

INFORMATION REGARDING

DIRECTOR NOMINEES AND CURRENT DIRECTORS

The following table sets forth, for the Class III nominees at the Annual Meeting, their ages, positions held and length

of service as of the date of this Proxy Statement. The brief biographies below include information, as of the date of

this Proxy Statement, regarding the specific and particular experience, qualifications, attributes or skills that led the

nominating and governance committee to believe that each director nominee should continue to serve on the board

of directors. There are no family relationships among any of our executive officers or directors.

Nominees	Age	Term Expires	Position(s) Held	Director Since
Lawrence Hilsheimer	68	2026	Director	2020
Alexander Timm	37	2026	Co-Founder, CEO and Director	2015
Douglas Ulman	48	2026	Director	2016

Nominees for Election at the 2026 Annual Meeting of Stockholders

Lawrence Hilsheimer. Mr. Hilsheimer has served as a member of our board of directors since October 2020. Since

May 2014, Mr. Hilsheimer has served as Executive Vice President and Chief Financial Officer of Greif, Inc.

(NYSE: GEF), an industrial manufacturing company. From April 2013 to April 2014, Mr. Hilsheimer served as

Executive Vice President and Chief Financial Officer of The Scotts Miracle-Gro Company (NYSE: SMG), a

multinational supplier of consumer gardening products. From October 2007 to March 2013, Mr. Hilsheimer served

in various executive roles with Nationwide Mutual Insurance Company, beginning as EVP/CFO, then as President

and Chief Operating Officer of Nationwide Direct and Customer Solutions with responsibility for its direct to

consumer sales and service, Nationwide Bank and Nationwide Better Health, before taking on the role of President

and Chief Operating Officer of Nationwide Retirement Plans with continuing responsibility for Nationwide Bank.

Prior to Nationwide, Mr. Hilsheimer served at Deloitte from 1979 through 2007, as a partner from 1988 through

2007, including as a Vice Chairman from 2005 through 2007. Mr. Hilsheimer is a director and Chairman of the

Audit Committee of Installed Building Products, Inc. (NYSE: IBP), an installer of insulation products. Since 2017,

Mr. Hilsheimer has served as a director of Root Insurance Company, a subsidiary of the Company, and served as

Chairman of its Audit Committee until such committee was dissolved in January 2021. Mr. Hilsheimer is certified in

cybersecurity oversight by the National Association of Corporate Directors. We believe Mr. Hilsheimer is qualified

to serve on our board of directors due to his management experience, his experience in the insurance industry, as a

chief financial officer and as an audit committee chairperson, and his existing relationship with the Company.

Alexander Timm. Mr. Timm has served as our Co-Founder, CEO and a member of our board of directors since our

founding in March 2015. From August 2011 to March 2015, Mr. Timm served in various management roles at

Nationwide Mutual Insurance Company, an insurance and financial services company. Mr. Timm served as a

member of the board of directors of GoHealth, Inc. (Nasdaq: GOCO), a digital health insurance marketplace, from

2020 to 2025. He is a 2023 Aspen Institute Henry Crown Fellow. He holds a Bachelor of Science and Bachelor of

Arts in Actuarial Science, Accounting and Mathematics from Drake University. He is also a fellow of the Casualty

Actuarial Society. We believe Mr. Timm is qualified to serve on our board of directors due to his perspective and

experience as our Co-Founder and CEO, as well as his experience in the insurance industry.

Douglas Ulman. Mr. Ulman has served as a member of our board of directors since December 2016. He currently

serves as Vice Chair of the Board of Pelotonia, a nonprofit based in Columbus, Ohio that has raised more than $360

million for cancer research since 2009. From December 2014 to January 2024, Mr. Ulman served as Chief Executive

Officer of Pelotonia. From 2008 to December 2014, he served as the President and Chief Executive Officer of The

LIVESTRONG Foundation. A social entrepreneur and community builder, Mr. Ulman founded the Ulman Cancer

Fund for Young Adults (now the Ulman Foundation) after his own cancer diagnosis. He also founded Orli, an

impact investment firm and philanthropic advisory platform, in 2022. He serves as the Chair of Signal Ohio’s board

and is a member of both The Columbus Partnership and Young Presidents’ Organization (YPO). He recently served

as a Hauser Fellow at Harvard University Kennedy School Center for Public Leadership. He holds a Bachelor of

Arts from Brown University and completed the Executive Program in Leadership at Stanford University. We believe

Mr. Ulman is qualified to serve on our board of directors due to his experience in executive leadership roles.

Information About Our Continuing Directors

The following table sets forth, for the remaining members of our board of directors whose terms continue beyond

the Annual Meeting, their ages, positions held and length of service as of the date of this Proxy Statement. The

principal occupation, business experience and education of each continuing director are set forth below. Unless

otherwise indicated, principal occupations shown for each director have extended for five or more years.

Continuing Directors	Age	Term Expires	Position(s) Held	Director Since
Beth Birnbaum	53	2027	Director	2022
Donna Dorsey	55	2027	Director	2023
Julie Szudarek	54	2027	Director	2022
Jerri DeVard	67	2028	Director	2020
Nancy Kramer	70	2028	Director	2020

Directors Continuing in Office Until the 2027 Annual Meeting of Stockholders

Beth Birnbaum. Ms. Birnbaum has served on our board of directors since March 2022. Ms. Birnbaum currently

serves as Chief Operating Officer of Mudstack, Inc., a platform for version control, management and review of

digital assets. Previously, Ms. Birnbaum served as Chief Operating Officer at PlayFab, Inc. (“PlayFab”), the

backend service platform for gaming acquired by Microsoft Corporation (Nasdaq: MSFT), from 2017 to 2018. Prior

to PlayFab, Ms. Birnbaum served in a variety of roles at GrubHub, Inc., from 2011 to 2016, most recently as Senior

Vice President of Product. From 2003 to 2011, Ms. Birnbaum served in a variety of roles at Expedia Group, Inc.

(Nasdaq: EXPE), an online travel company, most recently as Vice President of Product and Connectivity. Ms.

Birnbaum served on the board of directors of John Wiley & Sons, Inc. (NYSE: WLY and WLYB), a publishing

company specializing in scientific, technical, and medical books and journals, from 2018 to 2024. She holds a

Bachelor of Arts in Economics and International Studies from Yale University and a Master of Business

Administration from INSEAD. Ms. Birnbaum is Diligent Climate Leadership Certified. We believe Ms. Birnbaum is

qualified to serve on our board of directors due to her extensive operating experience in the technology industry, in

particular in the areas of product and general management, and her experience as a former director of another public

company.

Donna Dorsey . Ms. Dorsey has served as a member of our board of directors since October 2023. Since June 2025,

Ms. Dorsey has served as Chief Human Resources Officer of Alight Solutions, LLC, a leading cloud-based human

capital and technology-enabled services provider that helps large employers administer employee benefits and

manage human resources, health, wealth, well-being, and related workforce services. From 2015 to May 2025, Ms.

Dorsey served as Executive Vice President and Chief People & Culture Officer for International Motors, LLC

(“International Motors”), a manufacturer of commercial transportation vehicles. In this role, she was responsible for

all aspects of human resource strategy and provided strategic business and human capital leadership that drove

change and innovation at the company. Prior to that role, Ms. Dorsey led strategic human capital direction for all

business operations at International Motors while overseeing International Motors’ team of human capital business

partners. She holds a Bachelor of Arts in Political Science from Rutgers University and a Juris Doctor from

Chicago-Kent College of Law with a certification in labor and employment law. We believe Ms. Dorsey is qualified

to serve on our board of directors due to her extensive experience in the human capital management field, with an

emphasis on change and innovation.

Julie Szudarek. Ms. Szudarek has served as a member of our board of directors since July 2022. From October 2023

to March 2026, Ms. Szudarek served as the Chief Executive Officer of Self Financial, Inc. (“Self”), a credit building

platform working to increase economic inclusion and financial resilience through products that make building credit

accessible. Prior to joining Self, Ms. Szudarek served as Chief Executive Officer of Atida Mifarma (“Atida”), one of

the largest online pharmacies in Europe, from 2019 to January 2023. Before joining Atida, Ms. Szudarek held senior

leadership roles at Groupon Inc. (Nasdaq: GRPN) (“Groupon”), an online commerce marketplace, in sales,

operations, logistics, and administration from 2011 to 2018. Prior to Groupon, she served in a variety of roles at

Orbitz Worldwide, Inc. (acquired by Expedia), an online travel company, from 2005 to 2011. Earlier in her career,

Ms. Szudarek worked in management consulting at Accenture plc (formerly Andersen Consulting), a global

professional services company. Ms. Szudarek holds a Bachelor of Arts in Finance from Indiana University and a

Master of Business Administration from the University of Michigan. We believe Ms. Szudarek is qualified to serve

on our board of directors due to her experience driving e-commerce and technology-enabled businesses, including as

a former Chief Executive Officer.

Directors Continuing in Office Until the 2028 Annual Meeting of Stockholders

Jerri DeVard. Ms. DeVard has served as a member of our board of directors since October 2020. She is the Founder

of the Black Executive CMO Alliance (BECA), an alliance designed to champion corporate diversity and help build

the next generation of C-suite marketing executives. From January 2018 to March 2020, Ms. DeVard served as

EVP, Chief Customer Officer of Office Depot, Inc. (“Office Depot”), an office supply retailing company, where she

also served as EVP, Chief Marketing Officer from September 2017 to December 2017. Prior to Office Depot, Ms.

DeVard served as Senior Vice President and Chief Marketing Officer of The ADT Corporation (NYSE: ADT), a

home and business security company, from March 2014 through May 2016. She has also served in senior marketing

roles at Nokia Corporation, Verizon Communications Inc., Citibank N.A., Revlon Inc., Harrah’s Entertainment, the

Minnesota Vikings and the Pillsbury Company. Ms. DeVard is a graduate of Spelman College and Clark Atlanta

University Graduate School of Business. She currently serves on the Board of Directors of Under Armour, Inc.

(NYSE: UA), a sports equipment company, Cars.com Inc. (NYSE: CARS), an online automotive classified

company, and Dow Inc. (NYSE: DOW), a materials-science and packaging company. From 2016 to 2018, she

served as a member of the Board of Directors of ServiceMaster Global Holdings Inc., a residential and commercial

services company. We believe Ms. DeVard is qualified to serve on our board of directors due to her experience in

executive leadership roles, her marketing expertise and her experience serving on other public company boards of

directors.

Nancy Kramer. Ms. Kramer has served as a member of our board of directors since August 2020. Since August

2016, she has served as the Global Chief Evangelist of IBM iX (NYSE: IBM), a digital strategy and marketing

services division of IBM. She founded Resource/Ammirati, a marketing and creative agency, in 1981 with Apple

Computer as her first client, and served dozens of Fortune 500 companies, until its sale to IBM in 2016. In addition

to her role on our board of directors, she has served as a director of M/I Homes, Inc. (NYSE: MHO), a home

construction company, since 2015. From 2013 to 2015, Ms. Kramer served as a director of Glimcher Realty Trust, a

real estate investment trust, until its sale to Washington Prime Group in 2015. She holds a Bachelor of Arts from

The Ohio State University. We believe Ms. Kramer is qualified to serve on our board of directors due to her

experience in executive management roles and advising venture capital companies as well as her public company

director experience.

Board Summary

Total Number of Directors	8
Average Tenure (from IPO)	4.7 Years
Demographic Background	Female	Male
Gender Identity	5	3
African American or Black	2	—
White	3	3
LGBTQ+	1

Board Skills Matrix

Skills and Experience	Alexander Timm	Lawrence Hilsheimer	Douglas Ulman	Nancy Kramer	Jerri DeVard	Beth Birnbaum	Julie Szudarek	Donna Dorsey
C-Suite Executive	ü	ü	ü	ü	ü	ü	ü	ü
Insurance	ü	ü
Finance/Accounting	ü	ü			ü		ü
Technology/Cyber	ü	ü		ü		ü	ü
Human Capital			ü	ü			ü	ü
Innovation	ü		ü	ü	ü	ü	ü	ü
Brand Marketing			ü	ü	ü
Led Business Transformation	ü	ü	ü	ü	ü	ü	ü	ü
Gov’t/Regulatory/ Legal/Public Policy		ü	ü				ü	ü
Public Company Board	ü	ü		ü	ü	ü

INFORMATION REGARDING THE BOARD OF DIRECTORS

AND CORPORATE GOVERNANCE

Independence of the Board of Directors

Our Class A common stock is listed on the Nasdaq Stock Market (“Nasdaq”). Under the Nasdaq listing standards

(the “listing standards”), a majority of the members of our board of directors must qualify as “independent,” as

affirmatively determined by our board of directors. Our board of directors consults with our counsel to ensure that

its determinations are consistent with relevant securities and other laws and regulations regarding the definition of

“independent,” including those set forth in pertinent listing standards of Nasdaq, as in effect from time to time.

Consistent with these considerations, after review of all relevant identified transactions or relationships between

each director, any of his or her family members, Root, Root’s business partners, our senior management and our

independent auditors, our board of directors has affirmatively determined that Lawrence Hilsheimer, Julie Szudarek,

Nancy Kramer, Douglas Ulman, Jerri DeVard, Beth Birnbaum and Donna Dorsey do not have relationships that

would interfere with the exercise of independent judgment in carrying out the responsibilities of a director and that

each of these directors is “independent” as that term is defined under the listing standards. In making these

determinations, our board of directors considered the applicable listing standards, the current and prior relationships

that each non-employee director has with our company and all other facts and circumstances our board of directors

deemed relevant in determining their independence, including the beneficial ownership of our capital stock held by

each non-employee director and the transactions described in the section titled “ Transactions with Related Persons .”

Alexander Timm was not independent due to his position as an executive officer of Root. Accordingly, a majority of

our directors are independent, as required under applicable listing standards.

Board Leadership Structure

Our board of directors is committed to strong, independent board leadership and believes that objective oversight of

management is a critical aspect of effective corporate governance. Accordingly, while Mr. Timm serves as the

chairperson, Mr. Hilsheimer currently serves as lead independent director of our board of directors. The primary

responsibilities of the lead independent director are to: work with the CEO to develop board meeting schedules and

agendas; provide the CEO feedback on the quality, quantity and timeliness of the information provided to the board

of directors; develop the agenda for and moderate executive sessions of the independent members of the board of

directors; preside over board meetings when the chairperson is not present; act as principal liaison between the

independent members of the board of directors and the CEO; and convene meetings of the independent directors as

appropriate. Accordingly, the lead independent director has substantial ability to shape the work of the board of

directors. We believe that having a lead independent director supports the board of directors in its oversight of the

business and affairs of Root. In addition, we believe that having a lead independent director creates an environment

that is conducive to objective evaluation and oversight of management’s performance, increasing management

accountability and improving the ability of the board of directors to monitor whether management’s actions are in

the best interests of Root and its stockholders. As a result, Root believes that having a lead independent director can

enhance the effectiveness of the board of directors as a whole.

Role of the Board of Directors in Risk Oversight

Our board of directors oversees an enterprise-wide approach to risk management, designed to support the

achievement of organizational objectives, to improve long-term organizational performance and to enhance

stockholder value. A fundamental part of risk management is not only understanding the most significant risks a

company faces and what steps management is taking to manage those risks, but also understanding what level of risk

is appropriate for a given company. The involvement of our full board of directors in reviewing our business is an

integral aspect of its assessment of management’s tolerance for risk and also its determination of what constitutes an

appropriate level of risk.

While our full board of directors has overall responsibility for risk oversight, it has delegated oversight of certain

risks to its committees. Our audit, risk and finance committee monitors our major financial and security risk

exposures and the steps our management has taken to monitor and control these exposures, including guidelines and

policies to govern the process by which risk assessment and management is undertaken. Our audit, risk and finance

committee also monitors compliance with legal and regulatory requirements. Our compensation committee monitors

whether any of our compensation programs, policies and practices has the potential to encourage excessive risk-

taking. Our nominating and governance committee oversees our major corporate governance risks, including

through monitoring the effectiveness of our Corporate Governance Guidelines, and risks related to the Company’s

reputation through oversight of sustainability and corporate social responsibility matters.

In connection with its reviews of the operations of our business, the board of directors addresses the primary risks

associated with our business including, for example, strategic planning and cybersecurity. Our board of directors

appreciates the evolving nature of our business and industry and is actively involved with monitoring new threats

and risks as they emerge. In particular, our board of directors is committed to the prevention, timely detection and

mitigation of the effects of cybersecurity threats or incidents. Mr. Hilsheimer, the chair of the audit, risk and finance

committee, is certified in cybersecurity oversight by the National Association of Corporate Directors.

At periodic meetings of our board of directors and its committees, management reports to and seeks guidance from

our board of directors and its committees with respect to the most significant risks that could affect our business,

such as legal risks, information security and privacy risks and financial, tax and audit-related risks. In addition,

among other matters, management provides our audit, risk and finance committee periodic reports on our

compliance programs and investment policy and practices.

Meetings of the Board of Directors and its Committees

Our board of directors is responsible for the oversight of management and the strategy of our company and for

establishing corporate policies. Our board of directors meets periodically during the year to review significant

developments affecting us and to act on matters requiring the approval of our board of directors. Our board of

directors met five times during our last fiscal year. The audit, risk and finance committee met six times during our

last fiscal year. The compensation committee met four times during our last fiscal year. The nominating and

governance committee met four times during our last fiscal year. During our last fiscal year, each director attended

75% or more of the aggregate of the meetings of our board of directors and of the committees on which he or she

served. Although we do not have a formal policy regarding director attendance at our annual meeting of

stockholders, we encourage our directors and nominees for director to attend. Six of our eight directors attended the

annual meeting of stockholders held in 2025 (the “ 2025 Annual Meeting”) via webcast.

Composition of the Board of Directors and its Committees

Our board of directors has established an audit, risk and finance committee, a compensation committee and a

nominating and governance committee. Our board of directors has adopted a written charter for each of our standing

committees, which are available to stockholders on our investor relations website at ir.joinroot.com .

Our board of directors rotated committee chairs and membership in 2025 to ensure fresh perspectives. The following

table provides membership information and the total number of meetings for the fiscal year ended December 31,

2025 , for each of the standing committees of our board of directors, with committee designations as of

December 31, 2025 :

Name	Audit, Risk and Finance Committee	Compensation Committee	Nominating and Governance Committee
Alexander Timm
Julie Szudarek	Member†	Chair 1
Douglas Ulman 2		Member 1
Jerri DeVard 3			Chair 1
Lawrence Hilsheimer	Chair†
Beth Birnbaum 4	Member 1
Donna Dorsey		Member	Member 1
Nancy Kramer 5			Member 1
Total meetings held in 2025	6	4	4

† Audit Committee Financial Expert

(1) Effective October 30, 2025.

(2) Served on Audit Committee and Nominating and Governance Committee through October 30, 2025.

(3) Served as a member of Nominating and Governance Committee through October 30, 2025.

(4) Served on Compensation Committee through October 30, 2025.

(5) Served as chair of Compensation Committee through October 30, 2025.

Our board of directors has determined that each member of each standing committee meets the applicable listing

standards regarding “independence,” and each member is free of any relationship that would impair his or her

individual exercise of independent judgment with regard to us.

Our board of directors may establish other committees from time to time to facilitate the management of our

business. In addition to these three standing committees, the board of directors maintains a strategy committee,

which meets as necessary to generally oversee our business and marketing strategy. This committee is chaired by

Mr. Ulman, and Mses. DeVard and Kramer are members of the strategy committee. The strategy committee: reviews

and advises the board of directors on overall strategy, direction and effectiveness of the Company’s short- and long-

term goals and objectives, including goals and objectives related to its brand and marketing plans and strategies;

identifies and provides the board of directors with views on marketing and branding developments and trends that

are relevant to the Company and in alignment with the Company’s strategy and success of the Company’s product

sales and commercialization of its services; and advises the board of directors with respect to collaborations and

endorsement arrangements, and participation in other programs to enhance the Company’s value proposition and

visibility of its products in the marketplace. The strategy committee met three times in 2025 . In addition, the board

of directors maintains an executive committee, comprised of Messrs. Hilsheimer and Timm, which meets as

necessary to address matters that arise between board meetings and may exercise the powers and authority of the

board of directors, subject to specific limitations consistent with our Amended and Restated Bylaws and applicable

law.

Below is a description of each standing committee of our board of directors.

Audit, Risk and Finance Committee

Our audit, risk and finance committee is comprised of Lawrence Hilsheimer, Julie Szudarek and Beth Birnbaum.

Our board of directors has determined that each member of the audit, risk and finance committee during 2025

satisfied, and continues to satisfy, the independence requirements under the listing standards of Nasdaq Rule

5605(c)(2) and Rule 10A-3(b)(1) of the Exchange Act. The chair of our audit, risk and finance committee is Mr.

Hilsheimer. Our board of directors has determined that Mr. Hilsheimer and Ms. Szudarek are both “audit committee

financial experts” within the meaning of SEC regulations. Each member of our audit, risk and finance committee

can read and understand fundamental financial statements in accordance with applicable requirements. In arriving at

these determinations, our board of directors has examined each audit, risk and finance committee member’s scope of

experience and the nature of their employment.

The primary purpose of the audit, risk and finance committee is to discharge the responsibilities of our board of

directors with respect to our corporate accounting and financial reporting processes, systems of internal control and

financial statement audits and to oversee our independent registered public accounting firm. Specific responsibilities

of our audit, risk and finance committee include:

• overseeing the Company’s accounting and financial reporting processes, systems of internal control, financial

statement audits and the integrity of the Company’s financial statements;

• managing the selection, engagement terms, fees, qualifications, independence and performance of the registered

public accounting firms engaged as the Company’s independent outside auditors for the purpose of preparing or

issuing an audit report or performing audit services;

• maintaining and fostering an open avenue of communication with the Company’s management, internal audit

group and independent external auditors;

• reviewing any reports or disclosures required by applicable law and stock exchange listing requirements;

• overseeing organization and performance of the Company’s internal audit function and independent external

auditors;

• helping the board of directors oversee the Company’s compliance with legal and regulatory requirements;

• overseeing the identification and monitoring of important existing and emerging enterprise risks material to the

achievement of our strategic and operational objectives;

• reviewing and approving enterprise risk policies and procedures and determining risk appetite and tolerance

limits;

• reviewing and periodically evaluating the effectiveness of management processes and action plans to identify

and address enterprise risks and review and approve any reports or disclosures as required by applicable law;

• reviewing the status of any material tax audits and proceedings, our tax strategy and any other material tax

matters;

• reviewing and approving or recommending to the board of directors, as appropriate, all material financing plans,

including debt or equity issuances, share repurchases or dividends;

• overseeing matters related to data protection and security, as well as reviewing and establishing the design of an

information security program;

• reviewing our policies for investing in marketable securities and monitoring compliance with those policies;

• reviewing the scope of treasury risks;

• reviewing the adequacy of our insurance policies;

• reviewing long-term capital and liquidity polices; and

• providing regular reports and information to the board of directors.

Audit, Risk and Finance Committee Report

The audit, risk and finance committee has reviewed and discussed the audited financial statements and its report on

internal control over financial reporting for the fiscal year ended December 31, 2025 with our management. The

audit, risk and finance committee has also reviewed and discussed with Deloitte & Touche LLP, our independent

registered public accounting firm, the matters required to be discussed by the applicable requirements of the Public

Company Accounting Oversight Board (“PCAOB”) and the SEC. The audit, risk and finance committee has also

received the written disclosures and the letter from Deloitte & Touche LLP required by applicable requirements of

the PCAOB regarding the independent accountants’ communications with the audit, risk and finance committee

concerning independence and has discussed with Deloitte & Touche LLP the accounting firm’s independence.

Based on the foregoing, the audit, risk and finance committee has recommended to our board of directors that the

audited financial statements and the report on internal control be included in our Annual Report on Form 10-K for

the fiscal year ended December 31, 2025 and filed with the SEC.

Lawrence Hilsheimer, Chair

Julie Szudarek

Beth Birnbaum

The material in this report is not “soliciting material,” is not deemed “filed” with the Commission and is not to be

incorporated by reference in any filing of Root under the Securities Act of 1933, as amended (the “Securities Act”),

or the Exchange Act, whether made before or after the date hereof and irrespective of any general incorporation

language in any such filing.

Compensation Committee

Our compensation committee is comprised of Julie Szudarek, Donna Dorsey and Doug Ulman. The chair of our

compensation committee is Ms. Szudarek. Our board of directors has determined that each member of the

compensation committee that served on the compensation committee in 2025 and each member that continues to

serve on the compensation committee is independent under the applicable listing standards and a “non-employee

director” as defined in Rule 16b-3 under the Exchange Act.

The primary purpose of our compensation committee is to discharge the responsibilities of our board of directors in

overseeing our compensation programs, policies, and practices and to review and determine the compensation to be

paid to our executive officers, non-employee directors and other senior management, as appropriate. Specific

responsibilities of our compensation committee include:

• reviewing and approving, or recommending to our board of directors, the compensation of our CEO and other

executive officers;

• reviewing and approving, or recommending to our board of directors, the compensation of our non-employee

directors;

• administering (or providing for the administration of) our equity incentive plans and other benefit programs;

• reviewing and evaluating with the board of directors and our CEO succession plans for the Company’s

executive officers and making recommendations to the board of directors with respect to the selection of

appropriate individuals to succeed those positions;

• reviewing and discussing with management any Compensation Discussion and Analysis and report of the

compensation committee to be included in any filing with the SEC;

• reviewing and discussing with management any conflicts of interest raised by the work of the compensation

consultant or advisor hired by the compensation committee or management and preparing any necessary

disclosure in accordance with applicable law and applicable listing standards;

• reviewing, adopting, amending and terminating incentive compensation and equity plans, severance agreements,

profit sharing plans, bonus plans, change-of-control protections and any other compensatory arrangements for

our executive officers and other senior management;

• reviewing the Company’s practices and policies of employee compensation as they relate to risk management

and risk-taking incentives;

• reviewing and establishing general policies relating to compensation and benefits of our employees, including

our overall compensation philosophy; and

• monitoring and discussing with management any transactions involving the pledge of our common stock as

collateral pursuant to a loan agreement.

Compensation Committee Processes and Procedures

The compensation committee will generally meet quarterly and with greater frequency, if necessary. The

compensation committee also acts periodically by unanimous written consent in lieu of a formal meeting. The

agenda for each meeting is developed by the chair of the compensation committee, in consultation with

management. The compensation committee also meets in executive session without the presence of management.

However, from time to time, various members of management and other employees as well as outside advisors or

consultants may be invited by the compensation committee to make presentations, to provide financial or other

background information or advice or to otherwise participate in compensation committee meetings. Our CEO may

not participate in, or be present during, any deliberations or determinations of the compensation committee

regarding his compensation.

The charter of the compensation committee grants the compensation committee full access to all books, records,

facilities and personnel of Root. In addition, under the charter, the compensation committee has the authority to

obtain, at our expense, advice and assistance from compensation consultants and internal and external legal,

accounting or other advisors and other external resources that the compensation committee considers necessary or

appropriate in the performance of its duties. The compensation committee has direct responsibility for the oversight

of the work of any consultants or advisors engaged for the purpose of advising the compensation committee. In

particular, the compensation committee has the authority to retain compensation consultants to assist in its

evaluation of executive officer and non-employee director compensation, including the authority to approve the

consultant’s reasonable fees and other retention terms.

Generally, the compensation committee’s process for determining executive compensation is comprised of two

related elements: (i) the determination of compensation levels; and (ii) the establishment of performance objectives

for the current year. For executives other than our CEO, the compensation committee solicits and considers

evaluations and recommendations submitted to the compensation committee by our CEO. The compensation

committee considers the results of our CEO’s performance evaluation performed by the board of directors, and the

compensation committee determines any adjustments to his compensation as well as equity awards to be granted.

For all executive officers and non-employee directors, as part of its deliberations, the compensation committee may

review and consider, as appropriate, materials such as financial reports and projections, operational data, executive

and director stock ownership information, Company stock performance data, analyses of historical executive

compensation levels and current Company-wide compensation levels and, if applicable, recommendations of the

compensation committee’s compensation consultant, including analyses of executive and director compensation paid

at other companies identified by the consultant. For more information regarding the role of management and the

compensation consultant in determining or recommending the amount or form of executive compensation, see

“ Compensation Discussion and Analysis ” below.

To the extent permitted by the applicable listing standard requirements and applicable law, the compensation

committee is authorized under its charter to delegate any of its responsibilities to one or more subcommittees

comprised of one or more of members of the board of directors, and certain of its responsibilities to one or more

officers or other employees of the Company.

Compensation Committee Interlocks and Insider Participation

Mses. Szudarek (Chair), Kramer, Birnbaum and Dorsey and Mr. Ulman served on our compensation committee

during 2025 . The board of directors determined that each member qualified as independent. No member of the

compensation committee in 2025 was at any time during 2025 or at any other time an officer or employee of ours.

No committee member had any relationship with us requiring disclosure under Item 404 of Regulation S-K of the

Exchange Act. During 2025 , none of our executive officers served as a member on the board of directors or

compensation committee of any other for-profit entity that has an executive officer serving as a member of our

compensation committee or board of directors.

Communication with Compensation Committee Members

We believe constructive dialogue with our stockholders provides meaningful feedback about specific named

executive officer compensation practices and programs and encourage stockholders to communicate directly with

both management of the Company and the compensation committee about named executive officer compensation.

Stockholders may contact the compensation committee chair to provide input on named executive officer

compensation matters at any time by email at: [email protected].

Nominating and Governance Committee

Our nominating and governance committee is comprised of Jerri DeVard, Nancy Kramer and Donna Dorsey. The

chair of our nominating and governance committee is Ms. DeVard. Our board of directors has determined that each

member of the nominating and governance committee that served on the committee in 2025 and each member that

continues to serve on the committee is independent under the listing standards.

Specific responsibilities of our nominating and governance committee include:

• identifying and evaluating candidates, including the nomination of incumbent directors for reelection and

nominees recommended by stockholders, to serve on our board of directors;

• considering and making recommendations to our board of directors regarding the composition and chairmanship

of the committees of our board of directors;

• developing and making recommendations to our board of directors regarding corporate governance guidelines

and matters;

• overseeing the process for periodic evaluations of the board of directors’ performance, including committees of

the board of directors and approving the retention of director search firms;

• overseeing and providing input to management on our risks, policies, strategies and programs related to matters

of sustainability, corporate social responsibility and governance;

• reviewing and discussing with the board of directors the Company’s engagement with stockholders and

responsiveness to stockholder votes on governance matters; and

• overseeing the Company’s disclosure of corporate governance practices and policies and environmental, social

and governance initiatives and oversight.

The nominating and governance committee believes that candidates for director should have certain minimum

qualifications, including the ability to read and understand basic financial statements and having the highest personal

integrity and ethics. The nominating and governance committee also intends to consider such factors as possessing

relevant expertise upon which to be able to offer advice and guidance to management, having sufficient time to

devote to our affairs, demonstrated excellence in his or her field, having the ability to exercise sound business

judgment and having the commitment to rigorously represent the long-term interests of our stockholders. These

qualifications may be modified from time to time. Candidates for director nominees are reviewed in the context of

the current composition of the board of directors, the operating requirements of Root and the long-term interests of

our stockholders. In conducting this assessment, the nominating and governance committee typically considers

diversity (including gender identity, race, ethnicity, nationality, religion, disability, age and sexual orientation), skills

and such other factors as it deems appropriate, given the current needs of the board of directors and our business, to

maintain a balance of knowledge, experience and capability.

In the case of incumbent directors whose terms of office are set to expire, the nominating and governance committee

reviews these directors’ overall service to Root during their terms, including the number of meetings attended, level

of participation, quality of performance and any other relationships and transactions that might impair the directors’

independence. In the case of new director candidates, our nominating and governance committee also evaluates

whether the nominee is independent for Nasdaq purposes, based upon applicable listing standards, applicable SEC

rules and regulations and the advice of counsel, if necessary. Our nominating and governance committee conducts

any appropriate and necessary inquiries into the backgrounds and qualifications of potential candidates after

considering the function and needs of our board of directors. Our nominating and governance committee meets to

discuss and consider the candidates’ qualifications and then selects a nominee for recommendation to our board of

directors.

Our nominating and governance committee will consider stockholder recommendations of director candidates, so

long as they comply with applicable law and our Amended and Restated Bylaws, which procedures are summarized

below, and will review the qualifications of any such candidate in accordance with the criteria described in the two

preceding paragraphs. Stockholders who wish to recommend individuals for consideration by our nominating and

governance committee to become nominees for election to our board of directors should do so by delivering a

written recommendation to our nominating and governance committee at 80 E. Rich Street, Suite 500, Columbus,

Ohio 43215, Attention: Secretary, not later than the close of business on the 90th day nor earlier than the close of

business on the 120th day prior to the first anniversary of the Annual Meeting.

Each submission must include, among other things, the name, age, business address and residence address of the

proposed candidate, the principal occupation or employment of the proposed candidate, details of the proposed

candidate’s ownership of our capital stock, a description of the proposed candidate’s business experience for at least

the last five years and a description of the proposed candidate’s qualifications as a director. Any such submission

must be accompanied by the written consent of the proposed candidate to be named as a nominee and to serve as a

director if elected.

If, rather than submitting a candidate to the nominating and governance committee for consideration, you wish to

formally nominate a director pursuant to proxy materials that you will prepare and file with the SEC, please see the

deadline described in “ When are stockholder proposals due for next year’s annual meeting? ” above and refer to our

Amended and Restated Bylaws for a complete description of the required procedures for nominating a candidate to

our board of directors.

Evaluating Board and Committee Effectiveness

Our nominating and governance committee oversees the board of directors and committee self-evaluation process

that involves the opportunity for each member of the board of directors to complete detailed surveys and to

participate in a one-on-one facilitated interview with an independent third party, which process is designed to assess

the effectiveness of the board of directors as a whole and, separately, each of its committees. The surveys and

interview seek feedback on the board of directors and committee composition and organization, the frequency and

content of board of directors and committee meetings, the quality of management presentations to the board of

directors and its committees, the board of directors’ relationship to senior management, and the performance of the

board of directors and its committees in light of the responsibilities of each body established in our Corporate

Governance Guidelines and the respective committee charters. Our board of directors and each of its standing

committees performed a facilitated self-evaluation as described above beginning in late 2025 and met to review and

discuss the results in early 2026. Our nominating and governance committee views this process, which combines the

opportunity for each director to individually reflect on board of directors and committee effectiveness and to discuss

their views with a third-party facilitator followed by a collaborative discussion as providing a meaningful

assessment tool and a forum for discussing areas for improvement.

Stockholder Communications with the Board of Directors

Our board of directors has adopted a formal process by which stockholders may communicate with the board of

directors or any of its directors. Stockholders wishing to communicate with the board of directors or an individual

director may send a written communication c/o Root, Inc., 80 E. Rich Street, Suite 500, Columbus, Ohio 43215,

Attention: Secretary. Written communications may be submitted anonymously or confidentially and may, at the

discretion of the person submitting the communication, indicate whether the person is a stockholder or other

interested party. Each communication will be reviewed by the Secretary to determine whether it is appropriate for

presentation to the board of directors or such director. Examples of inappropriate communications include product

complaints, product inquiries, new product suggestions, resumes or job inquiries, surveys, solicitations or

advertisements or hostile communications.

Communications determined by the Secretary to be appropriate for presentation to the board of directors or such

director will be submitted to the board of directors or such director on a periodic basis. Communications determined

by the Secretary to be inappropriate for presentation will still be made available to any non-management director

upon such director’s request.

Code of Business Conduct and Ethics and Company Values

Our board of directors has adopted the Root, Inc. Code of Business Conduct and Ethics that applies to all officers,

non-employee directors and employees. In addition to applicable laws and regulations, our Code of Business

Conduct and Ethics, Company values and policies provide the grounding for our ethical framework. The Code of

Business Conduct and Ethics is available on our website at ir.joinroot.com . If we make any substantive amendments

to the Code of Business Conduct and Ethics or grant any waiver from a provision of the Code of Business Conduct

and Ethics to any executive officer or non-employee director, we will promptly disclose the nature of the

amendment or waiver on our website.

Employees are encouraged to report any unusual behavior or any non-compliant activities through a variety of

vehicles including our anonymous reporting system. On an annual basis, we provide ethics training on our Code of

Business Conduct and Ethics to, and require acknowledgement thereof by, every employee. We strive to ensure our

new employees know how and what to report and are encouraged through our values to challenge us and be

courageous. We have an open-door policy that empowers employees to reach out to leaders, our People team, our

compliance and/or internal audit teams to ensure that their concerns are heard and addressed.

Corporate Governance Guidelines

Our board of directors has adopted the Root, Inc. Corporate Governance Guidelines for the conduct and operation of

the board of directors in order to give directors a framework for effectively pursuing our objectives for the benefit of

our stockholders. The Corporate Governance Guidelines set forth the practices the board of directors intends to

follow with respect to board composition and selection, board meetings and involvement of senior management,

CEO performance evaluation, management succession planning and board committees and compensation. The

Corporate Governance Guidelines may be viewed on our website at ir.joinroot.com .

Insider Trading Policy; Prohibition on Hedging, Short Sales and Pledging

We have adopted the Amended and Restated Insider Trading Policy governing the purchase or sale of our securities

by our officers, employees and members of the board of directors, as well as designated consultants, and have

implemented procedures applicable to us, that we believe are reasonably designed to promote compliance with

insider trading laws, rules and regulations, and the applicable listing standards. A copy of our Amended and

Restated Insider Trading Policy is filed as Exhibit 19.1 to the Company’s Annual Report on Form 10-K for the year

ended December 31, 2025 .

Our Amended and Restated Insider Trading Policy also prohibits hedging or monetization transactions with respect

to our Class A common stock, including through the use of financial instruments such as prepaid variable forwards,

equity swaps, collars and exchange funds. In addition, our Amended and Restated Insider Trading Policy prohibits

trading in derivative securities related to our Class A common stock, which include publicly traded call and put

options, engaging in short selling of our Class A common stock, purchasing our Class A common stock on margin

or holding it in a margin account and, except by our non-employee directors and our executive officers with the prior

approval of our Chief Financial Officer and Chief Legal Officer and Secretary, pledging our shares as collateral for a

loan. None of our executive officers or non-employee directors have pledged our equity securities as of the date

hereof.

Corporate Social Responsibility at Root

Our board of directors has assigned oversight of risks, policies, strategies, and programs related to sustainability,

corporate social responsibility, and governance to the nominating and governance committee. Corporate social

responsibility (“CSR”) initiatives are led by the Chief Communications Officer and Chief Legal Officer and

Secretary.

Since our founding in 2015, Root has consistently pushed the boundaries of the insurance industry using technology

and data science to deliver customer-centric solutions. These solutions come with a commitment to our community,

our industry, and our planet. As we continue to innovate and evolve, so does our commitment to these principles.

In addition to the highlights below, Root’s actuarial and data science teams continue to closely monitor factors such

as climate, seasonality, and catastrophic events and their potential impact on the Company’s financial performance.

In parallel, our enterprise risk management working group proactively identifies, monitors, and mitigates emerging

risks across the organization to support resilient operations and long-term financial stability. To further raise

awareness of safer driving behaviors, the Company launched a further iteration of its Focused Driving Report,

highlighting the states and cities with the most and fewest focused drivers.

Additional 2025 Highlights

Information Security and Privacy

Our board of directors, through its audit, risk and finance committee, oversees the implementation and maintenance

of an Information Security Program designed to protect the confidentiality, integrity, and availability of our

information systems and data (including nonpublic information in our possession, custody, or control), as well as

comply with privacy and information security program requirements for insurers as set forth in applicable state laws

and regulations. Mr. Hilsheimer, the chair of the audit, risk and finance committee, is certified in cybersecurity

oversight by the National Association of Corporate Directors.

The board of directors, or its delegate, is required to receive an annual report of the Information Security Program.

The topics covered by these reports include overall status and compliance, any material matters, recommendations

for changes to the Information Security Program, results from risk assessments and other testing, any security events

and management responses to the same. The Chief Information Security Officer leads day-to-day management of

our Information Security program. All of our employees are required to participate in information security and

privacy training on a monthly basis. The Incident Response team, led by our Chief Legal Officer and Secretary,

escalates material information security incidents to our executive officers and the board of directors.

Where to find more information . Our governance documents, including our Amended and Restated Certificate of

Incorporation, Amended and Restated Bylaws, committee charters, policies and other key disclosures can be found

under “Governance” and “Documents & Charters” on our website at ir.joinroot.com .

NON-EMPLOYEE DIRECTOR COMPENSATION

Non-Employee Director Compensation Policy

The non-employee director compensation policy (the “Director Compensation Policy”) was modified in May 2025, adjusting director retention amounts, as reflected below. These modifications are designed to enable us to attract and retain, on a long-term basis, highly qualified non-employee directors. Under the Director Compensation Policy, each director who is not an employee of Root is eligible to receive the following annual cash retainers for their service, effective May 1, 2025:	Eff. May 2025 Member ($)	Eff. May 2025 Chair ($) (1)		Prior Member ($)	Prior Chair ($) (2)
Board of Directors	85,000	20,000	(3)	85,000	20,000	(3)
Audit, Risk and Finance Committee	10,000	22,500		10,000	20,000
Compensation Committee	7,500	17,500		7,500	15,000
Nominating and Governance Committee	5,000	12,500		5,000	10,000
Strategy Committee	5,000	12,500		5,000	10,000

(1) Effective May 2025, the amounts listed in this column for committee chairs are paid in lieu of amounts received for applicable committee

member service.

(2) Prior to May 2025, the amounts listed in this column for committee chairs were paid in addition to amounts received for applicable

committee member service.

(3) An additional annual retainer of $22,500 (previously $20,000) is also provided to our lead independent director and paid in addition to the

board member retainer.

The cash compensation described above is payable to our eligible non-employee directors in equal quarterly

installments. Non-employee directors also receive reimbursement for out-of-pocket expenses incurred in connection

with attendance at meetings of the board of directors and committees.

The Director Compensation Policy provides for an initial RSU grant to new directors and an annual RSU grant for

then-serving directors with a value up to $175,000, with the initial RSU grant reflecting a prorated amount

commensurate with a new director’s election date. The grant for 2025 of 1,119 RSUs had a targeted value of

$150,000, generally vesting on the date of the 2026 Annual Meeting. For 2025, the value of each RSU award

granted under the Director Compensation Policy was based on the targeted value divided by the closing price of a

share of our Class A common stock on the date of grant, conforming with the methodology utilized for employee

RSU grants.

Under the Director Compensation Policy, each director may make an election to defer delivery of shares in

settlement of RSU awards until such director retires from board service, or until immediately prior to a “change in

control” (as defined in our 2020 Equity Incentive Plan (the “2020 Plan”)). In addition, each RSU held by a non-

employee director who remains in service until immediately prior to a change in control of Root will become fully

vested as of immediately prior to the closing of such change in control transaction.

The aggregate value of all compensation granted or paid to any non-employee director with respect to any calendar

year, including awards granted and cash fees paid by us to such non-employee director, may not exceed $650,000 in

total value, or if such non-employee director is first appointed or elected to our board of directors during such

calendar year, $900,000 in total value.

Notwithstanding the Director Compensation Policy, our board of directors or the compensation committee may

make supplemental grants to our non-employee directors in its discretion (subject to the limits described in the

preceding paragraph).

2025 Non-Employee Director Compensation Table

The following table sets forth information regarding the compensation earned for service on the board of directors

by our non-employee directors during the year ended December 31, 2025 . The compensation for Mr. Timm, who

served as a named executive officer and employee director, is set forth below under “ — 2025 Summary

Compensation Table .”

Name	Fees Earned or Paid in Cash ($) (1)		Stock Awards ($) (2)(3)	Total ($)
Douglas Ulman	108,021		149,935	257,956
Jerri DeVard	103,125		149,935	253,060
Lawrence Hilsheimer	157,250	(4)	149,935	307,185
Nancy Kramer	108,229		149,935	258,164
Beth Birnbaum	92,917		149,935	242,852
Julie Szudarek	123,917	(4)	149,935	273,852
Donna Dorsey	93,333		149,935	243,268

(1) Reflects proration for changes to board and committee member retainers in May 2025 and changes to committee service during the year.

(2) The amounts reported in this column reflect the aggregate grant date fair values of the stock awards granted to our non-employee directors

as computed in accordance with the Financial Accounting Standards Board’s (“FASB”) Accounting Standards Codification Topic 718

(“ASC Topic 718”). See Note 2 to the Consolidated Financial Statements in our Annual Report on Form 10-K for the year ended

December 31, 2025 , for a discussion of the assumptions made in determining the aggregate grant date fair value of our stock awards. Note

that the amounts reported in this column reflect the accounting cost for these awards, and do not reflect the actual economic value that may

be realized by the non-employee directors upon the vesting of the awards or the sale of the Class A common stock underlying such awards.

These awards were granted to each of our non-employee directors on the date of our 2025 Annual Meeting (June 4, 2025) pursuant to the

Director Compensation Policy and consist of grants of 1,119 RSUs generally vesting on the date of our 2026 Annual Meeting.

(3) The following table provides information regarding the aggregate number of shares of our Class A common stock or Class B common stock

that were subject to the equity awards granted to our non-employee directors that were outstanding as of December 31, 2025 :

Name	Stock Awards Outstanding at Year-End (#)	Option Awards Outstanding at Year-End (#)
Douglas Ulman	1,119	33,352
Jerri DeVard	1,119	—
Lawrence Hilsheimer	1,119	—
Nancy Kramer	1,119	4,166
Beth Birnbaum	1,119	—
Julie Szudarek	1,119	—
Donna Dorsey	1,119	—

(4) Fees earned or paid in cash includes $26,000 retainer for service on the boards of directors of our subsidiary insurance companies.

PROPOSAL 2 - RATIFICATION OF OUR SELECTION OF

INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

The audit, risk and finance committee of our board of directors has selected Deloitte & Touche LLP as our

independent registered public accounting firm for the fiscal year ending December 31, 2026 , and has further directed

that management submit the selection of its independent registered public accounting firm for ratification by the

stockholders at the Annual Meeting. Deloitte & Touche LLP has audited our financial statements since 2017.

Representatives of Deloitte & Touche LLP are expected to be present at the Annual Meeting. They will have an

opportunity to make a statement if they so desire and will be available to respond to appropriate questions.

Neither our Amended and Restated Bylaws nor other governing documents or law require stockholder ratification of

the selection of Deloitte & Touche LLP as our independent registered public accounting firm. However, the audit,

risk and finance committee is submitting the selection of Deloitte & Touche LLP to the stockholders for ratification

as a matter of good corporate practice. If the stockholders fail to ratify the selection, the audit, risk and finance

committee will reconsider whether or not to retain that firm. Even if the selection is ratified, the audit, risk and

finance committee in its discretion may direct the appointment of different independent auditors at any time during

the year if they determine that such a change would be in the best interests of Root and our stockholders.

The affirmative vote of the holders of a majority of the shares present by virtual attendance or represented by proxy

and entitled to vote on the matter at the Annual Meeting will be required to ratify the selection of Deloitte & Touche

LLP.

Principal Accountant Fees and Services

The following table represents aggregate fees billed to us by Deloitte & Touche LLP for the periods set forth below.

	Fiscal Year Ended — 2025	2024
Audit Fees (1)	$ 1,637,000	$ 1,147,346
Audit-Related Fees (2)	—	15,000
Tax Fees	—	—
All Other Fees (3)	103,460	4,074
Total Fees	$ 1,740,460	$ 1,166,420

(1) Audit fees consist of fees for professional services provided in connection with the audit of our annual consolidated financial statements, the

review of our quarterly consolidated financial statements and audit services that are normally provided by an independent registered public

accounting firm in connection with statutory and regulatory filings or engagements for those fiscal years.

(2) Audit-related fees consist of fees for professional services that are reasonably related to performance of the audit or review of our financial

statements .

(3) All other fees consist of market research services and software license fees.

All fees described above were pre-approved by the audit, risk and finance committee.

Pre-Approval Policies and Procedures

The audit, risk and finance committee approves all audit and non-audit related services that our independent

registered public accounting firm provides to us before the engagement begins. Pre-approval may be given as part of

our audit, risk and finance committee’s approval of the scope of the engagement of the independent registered public

accounting firm or on an individual, explicit, case-by-case basis before the independent registered public accounting

firm is engaged to provide each service.

OUR BOARD OF DIRECTORS RECOMMENDS A VOTE “FOR” THE

RATIFICATION OF THE SELECTION OF DELOITTE & TOUCHE LLP

AS OUR INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM.

EXECUTIVE OFFICERS

The following table sets forth, for our executive officers, their ages and position held with us as of the date of this

Proxy Statement:

Name	Age	Principal Position
Alexander Timm	37	Co-Founder, CEO and Director
Megan Binkley	42	Chief Financial Officer
Mahtiyar Bonakdarpour	39	President and Chief Technology Officer
Jonathan Allison	59	Chief Administrative Officer

Biographical information for Alexander Timm is included above with the director biographies under the caption

“ Information Regarding Director Nominees and Current Directors .”

Megan Binkley . Ms. Binkley has served as our Chief Financial Officer since March 2023. Prior to that, she was

Deputy Chief Financial Officer from November 2022 to March 2023 and Chief Accounting Officer from April 2019

to November 2022. Prior to joining the Company, Ms. Binkley held roles of increasing responsibility at KPMG

LLP, a public accounting firm, from September 2007 until March 2019, at which time she was a senior manager.

Mahtiyar Bonakdarpour. Mr. Bonakdarpour has served as our President since February 2024 and Chief Technology

Officer since February 2022. Prior to that, he was our Chief Data Science and Analytics Officer beginning in July

2021, and our Vice President of Data Science beginning in July 2018. Mr. Bonakdarpour was a visiting scholar at

Yale University from September 2017 until March 2019 and a research assistant at the University of Chicago from

September 2014 until March 2019.

Jonathan Allison. Mr. Allison has served as our Chief Administrative Officer since May 2023. Prior to that, he was

our General Counsel from November 2017 to June 2023. Prior to joining the Company, Mr. Allison was an

Executive Vice President at CareSource, a managed care plan, from May 2015 to June 2017 and a partner at

Carpenter Lipps, LLP, a law firm, from December 2010 to May 2015.

COMPENSATION DISCUSSION AND ANALYSIS

Overview

Root is a technology insurance company founded on the idea that car insurance rates should be based primarily on

driving behaviors, not demographics. We are revolutionizing the archaic car insurance industry by using modern

technology, data science, and telematics to offer fair, personalized rates to good drivers. We primarily reach

customers through two channels: our direct channel, where we target consumers with what we believe to be a great

insurance product at a great price, and through our partnership channel, where we meet consumers at contextually

relevant times, such as during the car purchasing experience or through independent insurance agents . Our primary

focus is the U.S. auto insurance market, and we have built a company that recognizes each individual has unique

behaviors and that customers should be in control and rewarded for their actions.

This Compensation Discussion and Analysis provides an overview and analysis of our compensation programs with

respect to the following current executive officers, who we refer to throughout as our “named executive officers” or

“NEOs.”

Our 2025 Named Executive Officers
Alexander Timm Co-Founder and CEO Megan Binkley Chief Financial Officer	Mahtiyar Bonakdarpour President and Chief Technology Officer Jonathan Allison Chief Administrative Officer

2025 Program Highlights
Named executive officer long-term incentives granted solely in the form of Performance Share Units
Reinforces pay-for-performance philosophy
New Performance Share Unit design with a cumulative three-year performance period
Focuses on long-term profitable growth
Adoption of stock ownership guidelines
Helps align executive officer and non-employee director interests with those of stockholders
Four consecutive “Say-on-Pay” voting results above 90%
We continue to assess the executive compensation program to address stockholder concerns

2025 Company Performance

In 2025 , we continued to build on the momentum from the prior year by achieving our second consecutive year of

profitability, while growing gross written premiums by 16% when compared to 2024 . Our partnership channel

continued to be an important source of growth for the Company and by the fourth quarter represented 45% of all

new writings. The partnership channel in combination with our direct-to-consumer channel led to an overall policies

in force increase of 16 % when compared to 2024 . Our 2025 gross accident period loss ratio of 59.3 % continued to

be one of the industry’s best.

2025 Key Executive Compensation Results

Our annual incentive compensation program was directly linked to the continued profitable growth of the Company

by balancing the key metrics of New Writings and Adjusted EBITDA. The compensation committee’s assessment of

2025 performance resulted in funding of 150% of target. Equity awards granted in 2025 were delivered in the form

of Performance Share Units (“PSUs”) designed to align a significant part of the named executive officers’ total

compensation with the Company’s financial performance. The PSUs can be earned upon the achievement of

predetermined Policies In Force and Gross Accident Period Loss Ratio goals (as defined below), with the potential

to earn 200% of target units over the full three-year performance period, which is divided into three overlapping

sub-performance periods of one, two, and three years. Earning opportunities are backloaded to the most heavily

weighted three-year performance period. The one-year sub-performance period was completed at the end of 2025 ,

which resulted in vesting of 20% of the target shares awarded.

Executive Compensation Philosophy

Our executive compensation program reflects our overall corporate mission to provide fair, personal, and simpler

programs with a goal to recruit and retain those with the ability to accomplish Root’s revolutionary work. We

annually review the compensation of our executive leadership, including our named executive officers, to help

ensure it is market-competitive and aligned with stockholders’ interests. We also review our executive compensation

program against Root’s financial and strategic initiatives to provide incentives that help position Root to build a

world class insurance company .

Our program emphasizes a pay-for-performance approach to compensation by tying a majority of our named

executive officers’ compensation to Root’s financial performance via short- and long-term incentives. Long-term

incentives represent the largest portion of named executive officers’ target compensation and in 2025 were granted

solely in the form of PSUs that can be earned upon achievement of predetermined financial metrics and reward long-

term profitable growth. The focus on performance-based equity and the overall pay-for-performance approach helps

align the named executive officers’ pay outcomes directly with stockholder interests. Any appreciation or

depreciation in share price will also have a direct impact to the named executive officers’ equity incentives, with

realizable values experiencing the same appreciation or depreciation.

The pay-for-performance correlation is illustrated in the exhibit below, which displays our CEO’s target

compensation and estimated realizable compensation for years 2021 through 20 25 in comparison to Annual Total

Stockholder Return. With a majority of our CEO’s total compensation tied to long-term incentives, compensation is

closely tied to share price performance.

Target CEO compensation is the sum of base salary, target annual incentive, and grant date fair value of equity

awards as disclosed in the Grants of Plan-Based Awards table in the applicable year.

Estimated realizable CEO compensation is the sum of base salary, non-equity incentive plan compensation paid for

the applicable year’s performance, the value of time-based equity granted that year as of the applicable vesting date

or December 31, 2025, if outstanding, and the value of performance-based equity granted that year as of the

applicable vesting date or based on estimated performance through December 31, 2025, if outstanding.

Annual Total Stockholder Return reflects the share price change between the beginning and end of the applicable

year.

Executive Compensation Policies and Practices

Our compensation committee reviews the design and structure of our executive compensation program on at least an

annual basis to help ensure consistency with our short-term and long-term business goals. Root seeks to achieve

program consistency using governance and compensation-related policies and practices, including the following:

What We Do	What We Don’t Do
☑ Independent Compensation Consultant Our compensation committee has engaged an independent compensation consultant, Compensia, a national compensation consulting firm, that performs no other services for Root. ☑ Independent Compensation Committee Our compensation committee is comprised solely of independent directors. ☑ Compensation Recovery (“Clawback”) Policy We have enacted a compensation recovery policy that complies with the requirements of the SEC and the applicable Nasdaq listing standards to recover certain incentive-based compensation in the event of an accounting restatement or other action deemed to cause financial or reputational harm, as further described in such policy. ☑ Annual Say-On-Pay Vote We solicit an annual non-binding stockholder advisory vote to approve our named executive officer compensation. ☑ Reward Performance Over Multiple Time Horizons Our compensation program is structured to encourage our named executive officers to deliver strong results over the short term, while making decisions that create long-term sustained value over time for our stockholders. ☑ Compensation At-Risk In order to align the interests of our named executive officers with those of our stockholders, a significant portion of the target total direct compensation for our named executive officers is equity-based and/or “at risk,” subject to Company performance. ☑ Succession Planning The compensation committee periodically reviews succession plans for key executive positions.	☒ Perquisites and Other Benefits Unless deemed necessary to ensure business continuity, we generally do not offer perquisites or other personal benefits to our named executive officers that are not widely available to all full-time employees. ☒ Stock Option Repricing We have not repriced out-of-the-money stock options granted to our named executive officers. ☒ Hedging and Pledging of our Equity Securities We prohibit our employees, including our named executive officers and the non-employee members of our board of directors, from hedging our equity securities or purchasing our equity securities on margin or holding them in a margin account. Pledging our shares as collateral for a loan is also prohibited except by our non-employee directors and our executive officers with the prior approval of our CFO and Chief Legal Officer and Secretary. None of our executive officers or non-employee directors has pledged our equity securities as of the date of this Proxy Statement. ☒ No Separate Executive Retirement Plans We do not offer defined benefit pension plans or any non- qualified deferred compensation plans to our named executive officers other than the plans and arrangements that are available to all our other employees. Our named executive officers are eligible to participate in our Section 401(k) retirement savings plan on the same basis as our other employees. ☒ No Guaranteed Salary Increases or Bonuses Our named executive officers are not guaranteed an annual salary increase or bonus, whether discretionary or as part of the annual incentive program.

What We Do

What We Don’t Do

☑ Independent Compensation Consultant Our compensation committee has engaged an independent compensation consultant, Compensia, a national compensation consulting firm, that performs no other services for Root. ☑ Independent Compensation Committee Our compensation committee is comprised solely of independent directors. ☑ Compensation Recovery (“Clawback”) Policy We have enacted a compensation recovery policy that complies with the requirements of the SEC and the applicable Nasdaq listing standards to recover certain incentive-based compensation in the event of an accounting restatement or other action deemed to cause financial or reputational harm, as further described in such policy. ☑ Annual Say-On-Pay Vote We solicit an annual non-binding stockholder advisory vote to approve our named executive officer compensation. ☑ Reward Performance Over Multiple Time Horizons Our compensation program is structured to encourage our named executive officers to deliver strong results over the short term, while making decisions that create long-term sustained value over time for our stockholders. ☑ Compensation At-Risk In order to align the interests of our named executive officers with those of our stockholders, a significant portion of the target total direct compensation for our named executive officers is equity-based and/or “at risk,” subject to Company performance. ☑ Succession Planning The compensation committee periodically reviews succession plans for key executive positions.

☒ Perquisites and Other Benefits Unless deemed necessary to ensure business continuity, we generally do not offer perquisites or other personal benefits to our named executive officers that are not widely available to all full-time employees. ☒ Stock Option Repricing We have not repriced out-of-the-money stock options granted to our named executive officers. ☒ Hedging and Pledging of our Equity Securities We prohibit our employees, including our named executive officers and the non-employee members of our board of directors, from hedging our equity securities or purchasing our equity securities on margin or holding them in a margin account. Pledging our shares as collateral for a loan is also prohibited except by our non-employee directors and our executive officers with the prior approval of our CFO and Chief Legal Officer and Secretary. None of our executive officers or non-employee directors has pledged our equity securities as of the date of this Proxy Statement. ☒ No Separate Executive Retirement Plans We do not offer defined benefit pension plans or any non- qualified deferred compensation plans to our named executive officers other than the plans and arrangements that are available to all our other employees. Our named executive officers are eligible to participate in our Section 401(k) retirement savings plan on the same basis as our other employees. ☒ No Guaranteed Salary Increases or Bonuses Our named executive officers are not guaranteed an annual salary increase or bonus, whether discretionary or as part of the annual incentive program.

Compensation Decision Making Process

Stockholder Advisory Vote on Named Executive Officer Compensation

At our 2025 Annual Meeting, we received approximately 92 % approval, based on the total shares present and

entitled to vote, for our annual advisory Say-on-Pay vote to approve the compensation of our named executive

officers. The 2025 result represents the fourth straight year of above 90% approval since the first vote in 2022 . Even

with these strong results, the compensation committee continues to assess the program to help ensure alignment with

stockholder interests and peer practices and its ability to retain and reward our named executive officers. The

compensation committee’s review of the program in 2025 led to the updated annual incentive plan and redesigned

PSU grants as described further below, along with the adoption of stock ownership guidelines.

Role of the Compensation Committee

The compensation committee oversees our executive compensation program policies, plans, and practices. The

compensation committee regularly meets with and without management present and has the final authority to

determine compensation programs, policies, and amounts to be paid to our named executive officers. Typically,

early in each year, the compensation committee will approve annual cash incentive award payouts, long-term

incentive compensation awards, and any adjustments to base salary or target annual cash incentive award

opportunities.

Role of Management

Our CEO, Chief Administration Officer, Chief Financial Officer, and Vice President of People regularly attended

compensation committee meetings in 2025 to provide information on our executive compensation program,

including financial analysis, recommendations for compensation elements, and updates on our ongoing incentive

compensation plans and awards. Our CEO provides recommendations to the compensation committee regarding the

compensation for his direct reports in his role as their manager. Our CEO is not present during the portions of the

compensation committee meetings when his compensation is discussed and determined.

Role of the Compensation Consultant

During 2025 , the compensation committee retained Compensia, Inc. (which we refer to as the “compensation

consultant” in this Proxy Statement) to provide support with respect to the oversight of our executive compensation

program. The consultant regularly attends compensation committee meetings, both with and without management

present, and the compensation committee will occasionally request reviews of market trends for plan design and

analyses of competitive market compensation information to assist with its decision-making. The compensation

consultant provides information, advice, and other requested support to our compensation committee, but does not

make decisions relating to the amount or design of our compensation program for our named executive officers.

The compensation committee has annually assessed Compensia’s independence and, after considering and assessing

all relevant factors (including those required by the SEC and Nasdaq) that could give rise to a potential conflict of

interest, concluded that Compensia’s work did not raise any conflicts of interest.

Comparative Compensation Information

The compensation committee uses a compensation peer group as a reference to assess competitive market practices

and to evaluate the 2025 compensation levels for our named executive officers and the non-employee director

compensation policy. The compensation committee reviews the peer group each year and makes adjustments to its

composition as necessary to help ensure that its members are comparable to Root. When reviewing the 2025 peer

group, the compensation committee considered relevant selection criteria, including company ownership structure,

headquarter country location, industry, market capitalization, revenue, and proximity to the completion of an initial

public offering, among other qualitative factors. Following its annual review of our peer group with the

compensation consultant in 2025 , the compensation committee determined that updates to the peer group were

necessary due to the increase in Root’s market capitalization and revenue, along with the continued evolution of the

peer group to be a balance of traditional insurers and Fintech/Insurtech companies, which reflects the talent market

we compete in and companies investors compare us against.

The following tables display the prior peer group, which was used for 2025 compensation decisions, and the new

peer group, which was approved in July 2025 and used for 2026 compensation decisions.

Prior Peer Group (1) — Ambac Financial Group AvidXchange Holdings The Baldwin Ins. Group EVERTEC Flywire	GoHealth Goosehead Insurance Guidewire Software HCI Group Int’l Money Express	Lemonade Lending Club Marqeta MoneyLion Palomar Holdings	Safety Ins. Group Tiptree United Fire Group Universal Ins. Holdings Upstart Holdings

(1) Relative to the peer group used for 2024 compensation decisions, Blend Labs, Donegal Group, eHealth, Heritage Insurance Holdings,

Lending Tree, Mercury General, NI Holdings, Select Quote, and Trean Insurance Group were removed while AvidXchange Holdings, The

Baldwin Ins. Group, EVERTEC, Flywire, GoHealth, Goosehead Insurance, Guidewire Software, Int’l Money Express, Lending Club,

Marqeta, MoneyLion, Palomar Holdings, and Upstart Holdings were added.

New Peer Group — AvidXchange Holdings Bread Financial Holdings The Baldwin Ins. Group EVERTEC Flywire	Guidewire Software HCI Group Lemonade Lending Club Marqeta	MoneyLion OneMain Holdings Palomar Holdings Safety Ins. Group Tiptree	Trupanion United Fire Group Universal Ins. Holdings Upstart Holdings WEX

In approving the new peer group, the compensation committee considered our reported trailing 12-month revenue,

as was publicly disclosed through June 2025, and 30-day average market capitalization as of June 2025, relative to

the proposed peer group, as follows:

75th Percentile ($1,453)

75th Percentile ($4,401)

Root ($ 1 ,271)

Median ($1,145)

Median ($2,208)

Root ($2,144)

25th Percentile ($597)

25th Percentile ($1,208)

To analyze the compensation practices of the companies in our compensation peer group, the compensation

consultant gathered data from public filings (primarily proxy statements) of the peer group companies. This market

data was then used as a reference point for the compensation committee to assess our current compensation program

in the course of its deliberations on compensation forms and amounts.

Key 2025 Compensation Program Elements

Our executive compensation program consists of three primary elements—base salary, an annual cash incentive

award opportunity and long-term incentive compensation in the form of equity awards, as displayed in the following

table:

Element	Purpose	Design
Base Salary	Fixed portion of the target annual total direct compensation to attract and retain named executive officers	Reviewed annually by the compensation committee to appropriately reflect each named executive officer’s scope and responsibilities in context of the external market
Annual Cash Incentive Opportunity	Program intended to motivate achievement of the Company’s annual financial and operating goals	For 2025 , based on the achievement of predetermined financial measures of New Writings and Adjusted EBITDA
Long-Term Incentive Compensation	Performance and service-based equity compensation to reward our named executive officers for meeting or exceeding key financial objectives and to help align compensation with stockholder value	For 2025 , delivered in the form of Performance Share Units and based on the achievement of predetermined financial measures of Policies In Force and Gross Accident Period Loss Ratio over a three-year performance period

A substantial portion of the target annual total direct compensation for our named executive officers is variable and

“at risk” and subject to Company and/or individual performance. The following exhibits display the CEO’s and

other NEOs’ average pay mix for 2025 , where 90% of the CEO’s and, on average, 86% of other NEOs’, target

annual total direct compensation was considered performance-based and “at risk.”

At Risk Compensation

2025 Base Salary

Base salary represents the fixed portion of the target annual total direct compensation of our named executive

officers. The base salary is intended to be market competitive but also is intended to generally reflect the named

executive officer’s scope of responsibilities, experience, and performance over time. For 2025 , as part of its annual

compensation review, the compensation committee reviewed the 2024 base salaries of our named executive officers.

The compensation committee determined that Mr. Timm’s, Mr. Bonakdarpour’s, and Mr. Allison’s current base

salaries were appropriate and consistent with the competitive market and no adjustments were made in 2025 , while

ap proving an increase to Ms. Binkley’s base salary to align with the competitive market. Our named executive

officers’ annual base salaries for 2024 and 2025 were as follows:

Name	2024 Base Salary	2025 Base Salary (1)	Change in Base Salary
A. Timm	$750,000	$750,000	—%
M. Binkley	$459,000	$500,000	9%
M. Bonakdarpour	$550,000	$550,000	—%
J. Allison	$520,000	$520,000	—%

(1) Ms. Binkley’s base salary increase was effective April 30, 2025.

2025 Annual Cash Incentive Program

Our named executive officers participate in our annual cash incentive award program, which is intended to motivate

our named executive officers to contribute to the achievement of Root’s annual financial and operating goals. For

2025 , as part of its annual review of our executive compensation program, the compensation committee approved

the Root, Inc. 2025 Short-Term Incentive Plan (the “ 2025 STI Plan”). Our compensation committee selects the

performance measures and sets target performance levels for the annual cash incentive award program that align

with the achievement of our financial and operational goals, with above-target payouts designed for exceeding the

target performance goals and below-target payouts, or no payouts, when the goals are not achieved.

Target Annual Cash Incentive Award Opportunities

Each participant in the 2025 STI Plan, including each of the named executive officers, was eligible to receive a

target annual cash incentive award opportunity, expressed as a percentage of his or her annual base salary. For 2025 ,

as part of its executive compensation review prepared by its compensation consultant, the compensation committee

reviewed the 2025 STI Plan targets of our named executive officers. Upon this review, the compensation committee

determined that the target annual cash incentive award opportunities for each of the named executive officers were

appropriate and consistent with the competitive market and thus required no change. The 2025 target annual cash

incentive award opportunities of our named executive officers under the 2025 STI Plan are set forth in the following

table:

Name	2024 Target Annual Incentive Opportunity as % of Base Salary	2025 Target Annual Incentive Opportunity as % of Base Salary
A. Timm	150%	150%
M. Binkley	75%	75%
M. Bonakdarpour	100%	100%
J. Allison	100%	100%

2025 Annual Cash Incentive Performance Award Measures

The compensation committee selected a performance matrix composed of New Writings and Adjusted EBITDA as

the Company-wide performance measures to be used to assess achievement of 2025 priorities and performance

under the 2025 STI Plan . The matrix balanced the performance between the two measures to incentivize the

continuous focus on profitable growth, while allowing for agile strategy changes in the event of adverse competitive

market shifts. The matrix consisted of the New Writings performance measure along one axis and Adjusted

EBITDA along the other axis with each combination corresponding to a funding percentage. In setting the

combination of New Writings and Adjusted EBITDA that represented the target funding, the committee considered

the prior-year actual performance along with the 2025 plan. The level of New Writings performance that represented

the target-level funding was set above the prior year actual, while the maximum level of New Writings performance

on the matrix called for almost doubling of prior-year actual performance achievement. In light of the above target-

level plan achievement in the prior year and increased competition in the insurance marketplace, the level of

Adjusted EBITDA performance that represented the target-level funding was set below the prior year actual

performance, while the maximum level of Adjusted EBITDA performance on the matrix called for doubling of prior

year actual performance achievement. Our named executive officers had the opportunity to achieve a payout of up to

300% of their target annual cash incentive award opportunity based on our actual achievement compared to the pre-

established targets for these performance measures, with payouts above 200% of target reserved for exceptional

performance.

For purposes of the 2025 STI Plan :

• “New Writin gs” is d efined as the count of new policies written based on the initial (term 1) policy effective date

in the calendar period 2025. Rewrites from previously canceled policies are considered. This metric is the best

measure of company growth, unaffected by offsets. New Writings are inclusive of direct and partnership

acquisition channels, and

• “Adjusted EBITDA,” a non-GAAP financial measure, is defined as net income (loss) excluding interest

expense, income tax expense, depreciation and amortization, share-based compensation, loss on extinguishment

of debt, warrant compensation expense, restructuring charges, legal fees and other items that do not reflect our

ongoing operating performance. For 2025, also excluding incremental short-term incentive payouts above target

and expense related to additional short-term incentive eligibility for employees. After these adjustments, the

resulting calculation represents expenses directly attributable to our operating performance. We use Adjusted

EBITDA as an internal performance measure in the management of our operations because we believe it

provides management and other users of our financial information useful insight into our results of operations

and underlying business performance. Adjusted EBITDA should not be viewed as a substitute for net income/

loss calculated under GAAP, and other companies may define Adjusted EBITDA differently.

Annual Cash Incentive Award Payouts

In February 2026 , the compensation committee assessed the performance against the predetermined matrix of New

Writings and Adjusted EBITDA in the 2025 STI Plan . The compensation committee first measured the performance

of actual 2025 New Writings and Adjusted EBITDA and determined that per the plan design the matrix

corresponded to 213% of target funding. After discussions with management and considering the guiding principle

under the 2025 STI Plan that payouts above 200% should occur only in the case of exceptional performance , the

compensation committee decided to exercise downward discretion to fund payouts at 150% of target in light of our

2025 total stockholder return and to calibrate pay outcomes with its broad assessment of Company performance for

the year. Accordingly, the named executive officers received the following cash payouts under the 2025 STI Plan :

Name	Target Annual Incentive Opportunity $	% of Target	Total Payout $
A. Timm	$1,125,000	150%	$1,687,500
M. Binkley	$375,000	150%	$562,500
M. Bonakdarpour	$550,000	150%	$825,000
J. Allison	$520,000	150%	$780,000

Long-Term Incentives

We believe that a significant component of our target annual total direct compensation opportunities for our named

executive officers should be target long-term incentive compensation in the form of equity awards. The

compensation committee has the ability to grant, and has previously granted, equity awards to named executive

officers in the form of stock options, restricted stock units (“RSUs”) and PSUs. Equity awards represent an

opportunity to realize value based on long-term stock price performance, and they serve as a tool to reward and help

retain our named executive officers.

As a result of its 2025 compensation review, the compensation committee granted equity awards to our named

executive officers in the form of PSUs (“ 2025 PSUs”) using a redesigned structure that measured performance over

three years. The 2025 PSUs, which were granted in May 2025 , may be earned depending on achievement of goals

related to a Gross Accident Period Loss Ratio and Policies In Force goal matrix. The overall performance period

begins on January 1, 2025 and ends on December 31, 2027 and is divided into three sub-performance periods, each

beginning on January 1, 2025 and ending on December 31 of 2025, 2026, and 2027, respectively. These sub-

performance periods are one, two, and three years in duration with a back-loaded, cumulative opportunity to earn up

to 200% of target PSUs at the conclusion of the overall three-year performance period. 2025 PSUs may be earned

and vest upon the conclusion of each sub-performance period as follows:

Sub-Performance Period	PSU Earning and Vesting Opportunity
January 1, 2025 to December 31, 2025	Up to 20% of target PSUs
January 1, 2025 to December 31, 2026	Up to 55% of target PSUs minus any PSUs earned in the prior sub- performance period
January 1, 2025 to December 31, 2027	Up to 200% of target PSUs minus any PSUs earned in the prior sub- performance periods

With the redesigned structure, we recognized an accelerated accounting expense in 2025 reflecting the three sub-

performance period nature of the grant. This impact is expected to normalize over time as three concurrent in-flight

grants are established, creating a more balanced and steady expense recognition pattern. See Notes 2 and 12 to the

Consolidated Financial Statements in our Annual Report on Form 10-K for the year ended December 31, 2025 for

additional share-based compensation policies and expense details.

For purposes of the 2025 PSUs:

• Policies In Force is defined as the number of current and active auto insurance policyholders underwritten by

the Company as of the performance period, and

• Gross Accident Period Loss Ratio, expressed as a percentage, is defined as all losses and claims expected to

arise from insured events that occurred during the applicable period regardless of when they are reported and

finally settled divided by gross premiums earned for the same period.

In determining the design of the 2025 PSUs, the compensation committee considered market-prevalent equity grant

practices and Root’s approach of granting only performance-based equity in lieu of a combination of both

performance-based and time-vesting equity. In determining the values of these awards, the compensation committee

considered the market analysis prepared by its consultant, the outstanding equity holdings of each named executive

officer, the impact of the award on Root’s dilution and the number of shares available for issuance under our 2020

Equity Incentive Plan.

The target 2025 PSUs granted to our named executive officers in 2025 were as follows :

Name	Target 2025 PSUs	2025 PSUs Grant Date Fair Value
A. Timm	43,681	$5,499,875
M. Binkley	20,848	$2,624,972
M. Bonakdarpour	29,386	$3,699,991
J. Allison	19,061	$2,399,971

Vested and Outstanding PSUs

The PSUs granted in 2023 were granted with the performance criteria consisting of four separate stock price targets

to be met only (1) on or following the satisfaction of certain time-based service conditions, and (2) if the applicable

pre-established stock price target is met or exceeded based on the average closing price per share of our Class A

common stock over a consecutive 45-trading-day period during the performance period. As of the end of 2025 , the

performance criteria was satisfied as follows:

Stock Price Target Tranche (1)	Stock Price		Time-Based Service Condition Status
	Target	Status
1	$16.76	Condition Satisfied	Condition Satisfied
2	$25.14	Condition Satisfied	Condition Satisfied
3	$33.52	Outstanding	Outstanding
4	$41.90	Outstanding	Outstanding

(1) In April 2025 the second stock price target of $25.14/share and applicable time-based service condition were met. The gross share payouts

realized by each of the named executive officers were as follows: Mr. Timm, 41,979; Ms. Binkley, 3,184; Mr. Bonakdarpour, 28,695; and

Mr. Allison, 4,295. The third stock price target of $33.52 and service condition were met in April 2026. The final stock price target of

$41.90 and service condition may be met on or after April 1, 2027.

The performance period for the 2024 PSUs and the first sub-performance period of the 2025 PSUs were completed

as of the end of 2025 and the payouts were as follows:

PSUs	Payout Percentage
2024 PSUs	154%
2025 PSUs: Sub-performance period January 1, 2025 to December 31, 2025	20% of target PSUs

The 2024 PSUs were earned after a one-year performance period, corresponding to calendar year 2025, upon the

achievement of predetermined goals tied to financial measures of 2025 Adjusted EBITDA and New Writings, with

the opportunity to earn 200% of target PSUs . The two financial measures were arranged in a matrix where a

combination of performance resulted in a predetermined payout percentage of 154%. In order to add retentive value

to the 2024 PSUs and to align the awards with long-term stockholder value, the earned PSUs are subject to an

additional time-vesting requirement where 25% of the earned PSUs vested upon certification of the results in

February 2026, and an additional 25% will vest on or about January 1 of each calendar year thereafter until the

award is fully time-vested.

The shares tied to the first sub-performance period of the 2025 PSUs were earned after a one-year performance

period corresponding to calendar year 2025, upon the achievement of predetermined goals tied to measures of Gross

Accident Period Loss Ratio and Policies In Force. The two financial measures were arranged in a matrix where a

combination of performance resulted in a predetermined payout percentage with a maximum of 20% of the full

target 2025 PSUs eligible to be earned in the first sub-performance period. Upon certification of the results in

February 2026, the maximum 20% of target shares were earned.

The two outstanding sub-performance periods of the 2025 PSUs are trending as follows:

PSUs	Trending Performance
2025 PSUs: Sub-performance period January 1, 2025 to December 31, 2026	Target
2025 PSUs: Sub-performance period January 1, 2025 to December 31, 2027	Above Target

Key Compensation Governance Policies

Hedging and Pledging Prohibitions

Root maintains anti-hedging provisions under its Amended and Restated Insider Trading Policy, which prohibits

employees, including named executive officers and the non-employee members of our board of directors from

engaging in hedging or participating in monetization transactions, including through the use of financial instruments

such as prepaid variable forwards, equity swaps, collars, and exchange funds, or purchasing our equity securities on

margin or holding them in a margin account. While employees generally may not pledge shares of our stock,

executive officers, certain other designated employees, and non-employee directors may pledge shares of the

Company’s stock as collateral with the prior approval of our CFO and Chief Legal Officer and Secretary or our CEO

in the case of the CFO and Chief Legal Officer and Secretary, or with notice to the Chief Legal Officer and

Secretary in the case of our non-employee directors. None of our executive officers or non-employee members of

our board of directors has pledged our equity securities as of the date of this Proxy Statement.

Clawback Policy

The Company maintains and operates a compensation recovery (“clawback”) policy that complies with the

requirements of Exchange Act Rule 10D-1 and the applicable Nasdaq listing standards to recover certain incentive-

based compensation in the event of an accounting restatement. In 2024, the policy was amended to allow for the

recovery of incentive-based compensation and other equity awards or compensation, other than base salary, in the

discretion of the compensation committee, in the event of an accounting restatement or where certain activity caused

serious financial or reputational damage to the Company, involving intentional misconduct or an intentional

violation of any of the Company’s rules or any applicable legal or regulatory requirements, or fraud during the

course of employment with the Company.

In addition, the Company’s equity grant agreements include a clawback provision to allow for compensation

recovery pursuant to any clawback policies that may be adopted or implemented from time to time by the Company,

as permitted under applicable law.

Evaluation of Compensation Program Risks

Compensia, the compensation committee’s compensation consultant, prepared a report regarding the design and

operation of our executive compensation program, to determine whether it might encourage inappropriate risk-

taking that could have a material adverse effect on the Company. Following a review of that report and the

Company’s review of its other compensation programs, the compensation committee determined that the Company’s

compensation programs do not encourage employees to take risks that are reasonably likely to have a material

adverse effect on the Company.

Executive Employment Agreements

We have entered into a letter agreement or an employment agreement with each of our named executive officers.

Each of our named executive officers also has executed our standard form of proprietary information and inventions

agreement. The principal terms of the letter and employment agreements are described below.

Mr. Timm

In January 2021, we entered into a letter agreement with Mr. Timm, which was amended in February 2022. Mr.

Timm’s employment is “at will” and may be terminated at any time, with or without cause (as such term is defined

in the letter agreement). However, under the letter agreement, Mr. Timm is eligible for severance payments and

benefits upon a termination of his employment with us under certain circumstances, including in connection with a

change in control of the Company as described in more detail below under the subsection titled “Potential Payments

and Benefits upon Termination or Change in Control.”

Ms. Binkley

In August 2022, we entered into an executive employment agreement with Ms. Binkley. Ms. Binkley’s employment

is “at will” and may be terminated at any time, with or without cause (as such term is defined in the employment

agreement). Under the agreement, Ms. Binkley is eligible for severance payments and benefits upon a termination of

her employment with us under certain circumstances, including in connection with a change in control of the

Company as described in more detail below under the subsection titled “Potential Payments and Benefits upon

Termination or Change in Control.”

Mr. Bonakdarpour

In December 2021, we entered into an executive employment agreement with Mr. Bonakdarpour. Mr.

Bonakdarpour’s employment is “at will” and may be terminated at any time, with or without cause (as such term is

defined in the employment agreement). Under the agreement, Mr. Bonakdarpour is eligible for severance payments

and benefits upon a termination of his employment with us under certain circumstances, including in connection

with a change in control of the Company as described in more detail below under the subsection titled “Potential

Payments and Benefits upon Termination or Change in Control.”

Mr. Allison

In November 2021, we entered into an executive employment agreement with Mr. Allison. Mr. Allison’s

employment is “at will” and may be terminated at any time, with or without cause (as such term is defined in the

employment agreement). Under the agreement, Mr. Allison is eligible for severance payments and benefits upon a

termination of his employment with us under certain circumstances, including in connection with a change in control

of the Company as described in more detail below under the subsection titled “Potential Payments and Benefits

upon Termination or Change in Control.”

Stock Ownership Guidelines

The board of directors expects all executive officers and non-employee directors to maintain ownership in the

Company in order to help align interests with those of stockholders. Accordingly, the compensation committee

adopted stock ownership guidelines for all executive officers and non-employee directors effective April 30, 2025.

The ownership guidelines are as follows:

Population	Guideline Multiple	Share Ownership Includes
Chief Executive Officer	5x current annual base salary	• Shares owned directly by the executive officer/ non-employee director or his or her spouse or minor children • Shares held in trust for the benefit of the executive/non-employee director or his or her spouse or minor children • Shares obtained through vesting of restricted stock or restricted stock units • Time-based vesting restricted stock or restricted stock units that are unvested and outstanding
Other Executive Officers	3x current annual base salary
Non-Employee Directors	5x current annual cash retainer

The ownership guidelines are expected to be satisfied within five years of being subject to the stock ownership

guidelines and thereafter maintained throughout the duration of the executive officer’s or non-employee director’s

tenure with the Company. Until the guideline is met, executive officers and non-employee directors are required to

retain an amount equal to 50% of the net shares received from the vesting of all time-based or performance-based

restricted stock or restricted stock units.

As of the last scheduled review, all executive officers and non-employee directors had satisfied their applicable

ownership guideline.

Other Compensation and Benefits

Health and Welfare Benefits

In addition to the compensation described below in the “ 2025 Summary Compensation Table,” a ll of our current

named executive officers are eligible to participate in our employee broad-based benefit plans, including our

medical, dental, vision, life, disability and accidental death and dismemberment insurance plans, in each case on the

same basis as all of our other employees. We pay the premiums for the basic life and disability insurance for all of

our employees, including our named executive officers.

We maintain the Root Retirement 401(k) Plan (the “401(k) Plan”), a broad-based plan that provides eligible U.S.

employees with an opportunity to save for retirement on a tax-advantaged basis. Eligible employees are able to defer

eligible compensation up to certain Internal Revenue Code (the “Code”) limits, which are updated annually.

Currently, we contribute the equivalent of 3% of the eligible employee’s earnings to their 401(k) account regardless

of the amount the employee contributes, subject to a one-year vesting requirement from date of hire. The 401(k)

Plan is intended to be qualified under Section 401(a) of the Code, with the related trust intended to be tax exempt

under Section 501(a) of the Code. As a tax-qualified retirement plan, contributions to the 401(k) Plan are deductible

by us when made and contributions and earnings on those amounts are not generally taxable to the employees until

withdrawn or distributed from the 401(k) Plan.

Perquisites and Other Personal Benefits

We generally do not provide perquisites or other personal benefits to our named executive officers that are not

widely made available to all full-time employees u nless they are deemed necessary to help ensure the safety and

well-being of our named executive officers . During 2025 , none of our named executive officers received perquisites

or other personal benefits in the amount of $10,000 or more, except Mr. Timm, who received certain security

services.

Compensation Committee Report

The compensation committee of the board of directors oversees Root’s compensation programs on behalf of the

board of directors. The compensation committee reviewed and discussed with management the “ Compensation

Discussion and Analysis ” section included in this Proxy Statement.

The compensation committee recommended to the board of directors that the “ Compensation Discussion and

Analysis ” be included in this Proxy Statement and incorporated by reference in our Annual Report on Form 10-K for

the year ended December 31, 2025 .

This report is provided by the following independent directors who constitute the compensation committee:

Julie Szudarek, Chair

Donna Dorsey

Doug Ulman

The material in this report is not “soliciting material,” is not deemed “filed” with the Commission and is not to be

incorporated by reference in any filing of Root under the Securities Act, or the Exchange Act, whether made before

or after the date hereof and irrespective of any general incorporation language in any such filing.

EXECUTIVE COMPENSATION TABLES

2025 Summary Compensation Table

The following table sets forth the compensation for the fiscal years ended December 31, 2025 , December 31, 2024 ,

and December 31, 2023 , as applicable, for our CEO, Chief Financial Officer and our other two named executive

officers.

Name and Principal Position	Year	Salary ($)	Bonus ($)	Stock Awards ($) (1)	Non-Equity Incentive Plan Compensation ($) (2)	All Other Compensation ($) (3)	Total ($)
Alexander Timm Chief Executive Officer	2025	750,000	–	5,499,875	1,687,500	225,973	8,163,348
	2024	750,000	–	6,504,587	3,375,000	23,533	10,653,120
	2023	750,000	2,600,000	2,121,471	3,206,250	10,085	8,687,806
Megan Binkley Chief Financial Officer	2025	484,704	–	2,624,972	562,500	10,685	3,682,861
	2024	449,846	–	2,838,942	1,032,750	10,425	4,331,963
Mahtiyar Bonakdarpour President & Chief Technology Officer	2025	550,000	–	3,699,991	825,000	10,685	5,085,676
	2024	541,346	–	5,001,939	1,650,000	5,757	7,199,042
	2023	500,000	1,275,000	1,503,127	900,000	10,085	4,188,212
Jonathan Allison Chief Administrative Officer	2025	520,000	–	2,399,971	780,000	10,685	3,710,656
	2024	514,615	–	2,703,935	1,560,000	22,606	4,801,156
	2023	488,846	600,000	703,593	1,425,000	36,085	3,253,524

(1) For 2025 , the aggregate grant date fair value of equity awards granted in 2025 to our named executive officers was determined in

accordance with FASB ASC Topic 718. See Note 2 to the Consolidated Financial Statements in our Annual Report on Form 10-K for the

year ended December 31, 2025 , for a discussion of the assumptions made in determining the aggregate grant date fair value of our stock

awards. The grant date fair value for 2025 PSUs is based on the grant date fair value of the underlying shares of common stock and based

on the probable outcome of the performance conditions. The value of the 2025 PSUs if maximum performance were to be achieved is as

follows: Mr. Timm, $10,999,749 ; Ms. Binkley, $5,249,943 ; Mr. Bonakdarpour, $7,399,983 ; and Mr. Allison, $4,799,941 . See

“Compensation Discussion and Analysis—Long-Term Incentives” above for more information about the stock awards.

(2) Amounts shown for 2025 represent 2025 annual cash incentive award payouts earned by our named executive officers under our annual

cash incentive award program based on achievement of Company performance measures. See “Compensation Discussion and Analysis—

2025 Annual Cash Incentive Performance Award Measures” above for more information about these incentive payouts.

(3) Amounts shown for 2025 represent Company matching contributions made to the 401(k) Plan and life insurance premiums paid by the

Company on behalf of our named executive officers. For Mr. Timm, amount for 2025 also includes the incremental cost of personal security

services as determined by the board of directors to be in the best interest of ensuring his safety and security. For more information, please

see the following table:

Name	2025 401(k) Plan Contributions ($)	2025 Life Insurance Plan Premiums ($)	2025 Security Benefits ($)	Total ($)
A. Timm	10,500	185	215,288	225,973
M. Binkley	10,500	185	—	10,685
M. Bonakdarpour	10,500	185	—	10,685
J. Allison	10,500	185	—	10,685

2025 Grants of Plan-Based Awards Table

The following table provides information on the following plan-based awards granted to our named executive

officers in 2025 .

Name	Award Type (1)	Grant Date — Threshold ($)	Target ($)	Maximum ($)	Estimated Future Payouts under Equity Incentive Plan Awards (3) — Threshold (#)	Target (#)	Maximum (#)	Grant Date Fair Value of Stock and Option Awards ($) (4)
A. Timm	Annual Incentive	562,500	1,125,000	3,375,000
	PSUs	5/21/2025			10,920	43,681	87,362	5,499,875
M. Binkley	Annual Incentive	187,500	375,000	1,125,000
	PSUs	5/21/2025			5,212	20,848	41,696	2,624,972
M. Bonakdarpour	Annual Incentive	275,000	550,000	1,650,000
	PSUs	5/21/2025			7,347	29,386	58,772	3,699,991
J. Allison	Annual Incentive	260,000	520,000	1,560,000
	PSUs	5/21/2025			4,765	19,061	38,122	2,399,971

(1) “Annual Incentive” refers to annual cash incentive award opportunities under our 2025 STI Plan that are earned based on Company

performance against certain pre-established measures. See “ Compensation Discussion and Analysis— 2025 Annual Cash Incentive

Performance Award Measures ” above. Each PSU represents a contingent right to receive one share of our Class A common stock upon

vesting of the award. See “ Compensation Discussion and Analysis—Long-Term Incentives ” above.

(2) These columns represent the potential cash payouts under the annual cash incentive award program for 2025 .

(3) These columns represent the threshold, target, and maximum number of PSUs that could be earned based on total three-year performance,

which performance depends upon the Company’s achievement against the performance measures of Policies in Force and Gross Accident

Period Loss Ratio.

(4) Reflects the aggregate grant date fair value of the PSU awards, determined in accordance with FASB ASC Topic 718.

Grants made in 2025 are described more fully in the “ Compensation Discussion and Analysis ” section of this Proxy

Statement. The material terms of the named executive officers’ employment agreements are described above under

“ Compensation Discussion and Analysis—Executive Employment Agreements ” and below under “ Potential

Payments and Benefits Upon Termination or Change in Control ”. More information concerning the amount of

salary in proportion to the total compensation of our named executive officers is provided under the section of this

Proxy Statement entitled “ Compensation Discussion and Analysis—Key 2025 Compensation Program Elements ”.

Outstanding Equity Awards at 2025 Fiscal Year-End Table

The following table shows certain information regarding outstanding equity awards held by our named executive

officers that remained outstanding as of December 31, 2025 .

Name	Grant Date	Option Awards — Number of Securities Underlying Unexercised Options (#) Exercisable	Option Exercise Price ($) (1)	Option Expiration Date	Stock Awards — Number of Shares or Units of Stock That Have Not Vested (#)	Market Value of Shares or Units of Stock That Have Not Vested ($) (2)	Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (#)	Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($) (2)
A. Timm	6/19/2018 (3)				12,088	873,116
	8/9/2023 (4)						146,927	10,612,537
	8/9/2023 (5)				78,290	5,654,887
	4/1/2024 (6)				7,672	554,149
	11/13/2024 (7)				113,659	8,209,590
	5/21/2025 (8)				8,736	631,001
	5/21/2025 (9)						78,626	5,679,156
M. Binkley	4/18/2019	972	43.20	4/17/2029
	8/29/2020	555	145.62	8/28/2030
	8/9/2023 (10)						11,146	805,076
	8/9/2023 (11)				36,234	2,617,182
	11/13/2024 (12)				57,868	4,179,806
	5/21/2025 (8)				4,170	301,199
	5/21/2025 (9)						37,526	2,710,503
M. Bonakdarpour	7/21/2018	3,240	12.20	7/20/2028
	4/18/2019	12,152	43.20	4/17/2029
	4/1/2022 (13)				7,360	531,613
	8/9/2023 (14)						100,433	7,254,276
	8/9/2023 (15)				56,285	4,065,466
	11/13/2024 (16)				101,958	7,364,426
	5/21/2025 (8)				5,877	424,496
	5/21/2025 (9)						52,895	3,820,606
J. Allison	12/13/2017	10,636	5.15	12/12/2027
	7/16/2019	1,388	43.20	7/15/2029
	8/9/2023 (17)						15,031	1,085,689
	8/9/2023 (18)				36,234	2,617,182
	11/13/2024 (19)				55,116	3,981,029
	5/21/2025 (8)				3,812	275,341
	5/21/2025 (9)						34,310	2,478,211

(1) All of the option awards were granted with a per share exercise price equal to the fair market value of one share of our common stock on the

date of grant.

(2) Market value represents the product of the closing price of a share of the Company’s Class A common stock on December 31, 2025 , of

$ 72.23 per share, multiplied by the number of RSUs or PSUs.

(3) Reflects the number of shares acquired upon exercise of stock options that remained unvested on December 31, 2025 . Stock options granted

to our named executive officers under the 2015 Equity Incentive Plan (as described below) permitted early exercise and, if such options are

or were exercised, the stock acquired upon the exercise of such options is restricted and subject to a repurchase right in favor of the

Company. Such repurchase right lapses, and vesting occurs, with respect to such restricted stock on the same vesting schedule as the

original stock option award. Restricted stock acquired by Mr. Timm upon the early exercise of stock options vests in equal monthly

installments through June 2026.

(4) 62,969 PSUs were earned and vested on April 1, 2026 and the remaining 83,958 PSUs are scheduled to vest on April 1, 2027, subject to

attainment of a specified stock price threshold.

(5) 32,997 RSUs vested on April 1, 2026 and the remaining 45,293 RSUs are scheduled to vest on April 1, 2027.

(6) These RSUs vested on April 1, 2026.

(7) Each of these PSUs granted for the fiscal 2025 performance period, which are deemed to be earned because the performance condition was

achieved at the end of 2025, are included in this column because the stock had not yet vested as of the last day of the fiscal year. 28,414

PSUs vested on February 19, 2026 and the remaining PSUs are scheduled to vest as to 28,415 units on January 1, 2027, 28,414 units on

January 1, 2028, and 28,416 units on January 1, 2029.

(8) Represents the portion of the 2025 PSUs, which vested for the fiscal 2025 sub-performance period, which are deemed to be earned because

the performance condition was achieved at the end of 2025, and are included in this column because the stock had not yet vested as of the

last day of the fiscal year. These PSUs vested and settled on February 19, 2026.

(9) Remaining 2025 PSUs are reported at maximum , of which a portion may be earned after the fiscal 2025 through fiscal 2026 sub-

performance period and the remainder may be earned after the overall fiscal 2025 through fiscal 2027 performance period with the

opportunity to earn 200% of the overall granted target PSUs subject to the achievement against a predetermined Gross Accident Period Loss

Ratio and Policies In Force goal matrix. See the “Estimated Future Payouts under Equity Incentive Plan Awards” columns of the “2025

Grants of Plan-Based Awards Table” table on page 44 of this Proxy Statement for the threshold, target, and maximum numbers of PSUs that

can be earned.

(10) 4,777 PSUs were earned and vested on April 1, 2026 and the remaining 6,369 PSUs are scheduled to vest on April 1, 2027, subject to

attainment of a specified stock price threshold.

(11) 18,117 RSUs vested on April 1, 2026 and the remaining 18,117 RSUs are scheduled to vest on April 1, 2027.

(12) Each of these PSUs granted for the fiscal 2025 performance period, which are deemed to be earned because the performance condition was

achieved at the end of 2025, are included in this column because the stock had not yet vested as of the last day of the fiscal year. 14,466

PSUs vested on February 19, 2026 and the remaining PSUs are scheduled to vest as to 14,467 units on January 1, 2027, 14,467 units on

January 1, 2028, and 14,468 units on January 1, 2029.

(13) 3,680 RSUs vested on January 2, 2026 and 3,680 RSUs vested on April 1, 2026.

(14) 43,043 PSUs were earned and vested on April 1, 2026 and the remaining 57,390 PSUs are scheduled to vest on April 1, 2027, subject to

attainment of a specified stock price threshold.

(15) 24,399 RSUs vested on April 1, 2026 and the remaining 31,886 RSUs are scheduled to vest on April 1, 2027.

(16) Each of these PSUs granted for the fiscal 2025 performance period, which are deemed to be earned because the performance condition was

achieved at the end of 2025, are included in this column because the stock had not yet vested as of the last day of the fiscal year. 25,490

PSUs vested on February 19, 2026 and the remaining PSUs are scheduled to vest as to 25,490 units on January 1, 2027, 25,490 units on

January 1, 2028, and 25,488 units on January 1, 2029.

(17) 6,442 PSUs were earned and vested on April 1, 2026 and the remaining 8,589 PSUs are scheduled to vest on April 1, 2027, subject to

attainment of a specified stock price threshold.

(18) 18,117 RSUs vested on April 1, 2026 and the remaining 18,117 RSUs are scheduled to vest on April 1, 2027.

(19) Each of these PSUs granted for the Fiscal 2025 performance period, which are deemed to be earned because the performance condition was

achieved at the end of fiscal 2025, are included in this column because the stock had not yet vested as of the last day of the fiscal year.

13,779 PSUs vested on February 19, 2026 and the remaining PSUs are scheduled to vest as to 13,780 units on January 1, 2027, 13,780 units

on January 1, 2028, and 13,777 units on January 1, 2029.

2025 Option Exercises and Stock Vested Table

The following table shows information regarding restricted stock or restricted stock units that vested during 2025 .

Name	Stock Awards — Number of Shares Acquired on Vesting (#)	Value Realized on Vesting ($) (3)
A. Timm	24,174 (1)	2,630,754
	70,324 (2)	9,005,049
M. Binkley	21,299 (2)	2,737,013
M. Bonakdarpour	60,313 (2)	7,372,327
J. Allison	22,399 (2)	2,863,427

(1) Reflects the number of shares of restricted stock (acquired upon early exercise of stock options) that vested during the year. Stock options

granted to our named executive officers under the 2015 Equity Incentive Plan permitted early exercise and, if such stock options were

exercised, the shares of our common stock acquired upon the exercise of such stock options were restricted. Vesting occurs with respect to

such restricted stock on the same vesting schedule as the original stock option award.

(2) Reflects the gross number of shares received upon the vesting of RSUs. Based on the tax withholding payment elections, the following

number of shares were withheld to cover taxes: Mr. Timm, 32,205; Ms. Binkley, 9,651; Mr. Bonakdarpour, 26,798; and Mr. Allison,

10,202.

(3) Reflects the fair market value per share of the underlying shares of Class A common stock as of the vesting date, multiplied by the number

of shares vested.

Potential Payments and Benefits Upon Termination or Change in Control

Pursuant to the letter and employment agreements described above that we have entered into with each of our named

executive officers, if we had terminated a named executive officer’s employment without “cause” (which does not

include termination by reason of death or disability) or if the named executive officer had resigned for “good

reason” (as such terms are defined in each applicable named executive officer’s letter agreement or employment

agreement), the named executive officer would have been entitled to the following severance payments and benefits:

• 12 months’ continuation of the NEO’s then-current base salary;

• in the case of Ms. Binkley and Messrs. Bonakdarpour and Allison, payment equal to the portion of the annual

short-term incentive, if any, to be awarded for the period beginning on January 1 of the year the termination

occurs through the date of the termination on a pro rata basis;

• up to 12 months of direct payment or reimbursement of COBRA premiums for the NEO and the NEO’s eligible

dependents;

• accelerated vesting and exercisability of the unvested portion of each of the NEO’s then-outstanding equity

awards that otherwise would have vested had the NEO remained employed for 12 months following the date of

such termination; and

• if such termination occurs upon or within 12 months following a change in control of the Company (as defined

in the 2020 Plan) instead of the accelerated vesting described in clause (iv) above, 100% of unvested equity

awards would fully vest and become exercisable.

In the event of a termination of employment by reason of death or disability, Ms. Binkley and Messrs. Bonakdarpour

and Allison are eligible for a payment equal to the portion of the annual short-term incentive, if any, to be awarded

for the period beginning on January 1 of the year the termination occurs through the date of the termination on a pro

rata basis.

In the event of a voluntary resignation, Mr. Timm is eligible to receive, pursuant to his employment agreement, 12

months of his base salary and up to 12 months of direct payment or reimbursement of COBRA premiums for

himself and his eligible dependents. Mr. Bonakdarpour is eligible to receive, pursuant to his employment agreement,

12 months of his base salary and payment equal to the portion of the annual short-term incentive, if any, to be

awarded for the period beginning on January 1 of the year the termination occurs through the date of the termination

on a pro rata basis.

Each named executive officer’s receipt of the severance payments and benefits described above would have been

subject to their timely execution and non-revocation of a release of claims in favor of the Company.

The following table summarizes the payments and benefits that would have been payable to the named executive

officers assuming a hypothetical termination occurred as of December 31, 2025 .

Name	Benefits and Payments	Voluntary Resignation ($)	Involuntary Termination Without Cause or Good Reason Resignation (No Change in Control) ($)	Involuntary Termination For Cause ($)	Involuntary Termination Without Cause or Good Reason Resignation (Change in Control) ($)	Death/ Disability ($) (1)
A. Timm	Cash Severance	750,000	750,000	—	750,000	—
	Short-Term Incentive	—	—	—	—	—
	Health Benefit Payments	27,440	27,440	—	27,440	—
	Equity Vesting (2)	—	11,042,233	—	29,059,357	29,059,357
M. Binkley	Cash Severance	—	500,000	—	500,000	—
	Short-Term Incentive (3)	—	375,000	—	375,000	375,000
	Health Benefit Payments	—	10,561	—	10,561	—
	Equity Vesting (2)	—	2,999,712	—	9,107,914	9,107,914
M. Bonakdarpour	Cash Severance	550,000	550,000	—	550,000	—
	Short-Term Incentive (3)	550,000	550,000	—	550,000	550,000
	Health Benefit Payments	—	—	—	—	—
	Equity Vesting (2)	—	7,668,587	—	21,338,331	21,338,331
J. Allison	Cash Severance	—	520,000	—	520,000	—
	Short-Term Incentive (3)	—	520,000	—	520,000	520,000
	Health Benefit Payments	—	—	—	—	—
	Equity Vesting (2)	—	3,044,495	—	9,060,676	9,060,676

(1) Equity values reflect acceleration of unvested grants in the event of death. The compensation committee has the discretion to accelerate

vesting in the event of a disability.

(2) Reflects the value of equity awards that would vest upon the noted termination of employment based on the closing stock price of our Class

A common stock on December 31, 2025 , of $ 72.23 per share.

(3) In the case of Short-Term Incentive payments, while the named executive officers had the rights described in the narrative above to receive

pro-rated payment of the 2025 Short-Term Incentive under certain scenarios, the Company retained the discretion in each case to determine

the amount of such pro-rated payment, including based on actual performance and any other criteria the Company deems relevant. For

purposes of this disclosure, each of the Short-Term Incentive payments is disclosed at the named executive officer’s target level for the full

year, but actual payment under non-hypothetical situations could be more or less than target, depending on the timing of the scenario and

the compensation committee’s use of discretion.

CEO Pay Ratio

Mr. Timm, our CEO, received annual total compensation of $ 8,163,348 in 2025 , as reflected in the “ 2025 Summary

Compensation Table.” We estimate that the median of the 2025 annual total compensation for all employees of the

Company as of December 31, 2025 (the “Determination Date”), excluding our CEO, w as $ 68,634 , wh ich amount

comprises all applicable elements of compensation for 2025 in accordance with Item 402(c)(2)(x) of Regulation S-K

(the “Median Annual Compensation”). The ratio of Mr. Timm’s annual 2025 total compensation to the Median

Annual Compensation was approximately 119 to 1. We note that due to our permitted use of reasonable estimates

and assumptions in preparing this pay ratio disclosure, the disclosure may involve a degree of imprecision, and thus,

the disclosure is a reasonable estimate calculated in a manner consistent with Item 402(u) of Regulation S-K using

the data and assumptions described above.

In addition to our CEO, we employed a total of 1,259 employees, representing all full-time, part-time, seasonal and

temporary employees of the Company, as of the Determination Date, of which all were based in the United States.

We evaluated 2025 Form W-2 box 1 income for these 1,259 employees to determine the Median Employee. In

determining the Median Employee, we did not annualize compensation for employees who worked less than all of

2025 .

Pay Versus Performance

The following table provides information regarding “C ompensation Actually Paid ” (“CAP”) to our named executive

officers as determined in accordance with Item 402(v) of Regulation S-K and as described below, as well as Root’s

total stockholder return, the total stockholder return of our peer group (which includes the same issuers included in

the peer group depicted in our stock performance graph), Root’s GAAP net income (loss) and Root’s Adjusted

EBITDA for the fiscal years ende d December 31, 2025 , 2024 , 2023 , 2022 , and 2021 .

Year (1)	Summary Compensation Table Total for PEO ($) (2)	CAP to PEO ($) (2)	Average Summary Compensation Table Total for Non-PEO NEOs ($)	Average CAP to Non-PEO NEOs ($) (2)	Value of Initial Fixed $100 Investment Based On: — Total Stockholder Return ($)	Peer Group Total Stockholder Return ($) (3)	Net Income (Loss) ($) (in millions)	Adjusted EBITDA ($) (4) (in millions)
2025	8,163,348	14,113,264	4,159,731	6,852,767	25.54	86.52	40	132
2024	10,653,120	33,628,828	5,444,054	14,275,890	25.67	92.13	31	112
2023	8,687,806	9,709,825	3,720,868	4,355,570	3.71	61.20	( 147 )	( 43 )
2022	5,126,730	( 3,002,565 )	5,231,713	1,612,583	1.59	50.59	( 298 )	( 186 )
2021	5,784,695	( 25,185,719 )	9,760,351	( 5,961,079 )	19.73	82.94	( 521 )	( 446 )

(1) The following table lists the PEO and non-PEO NEOs for each of fiscal years 2025 , 2024 , 2023 , 2022 , and 2021 .

Year	PEO	Non-PEO NEOs
2025	Alexander Timm	Megan Binkley, Mahtiyar Bonakdarpour, and Jonathan Allison
2024	Alexander Timm	Megan Binkley, Mahtiyar Bonakdarpour, and Jonathan Allison
2023	Alexander Timm	Mahtiyar Bonakdarpour and Jonathan Allison
2022	Alexander Timm	Robert Bateman, Mahtiyar Bonakdarpour, Daniel Rosenthal, and Hemal Shah
2021	Alexander Timm	Daniel Rosenthal, Hemal Shah, Anirban Kundu, and Daniel Manges

(2) “CAP to the PEO” and “Average CAP to Non-PEO NEOs” includes the amounts set forth in the “ 2025 Summary Compensation Table” total

columns above (or in prior years’ Summary Compensation Tables), adjusted as set forth in the table below, as determined by Item 402(v) of

Regulation S-K. Stock option grant date fair values are determined based on the Black-Scholes option pricing model as of the date of grant.

Adjustments have been made using stock option fair values based on the Black-Scholes option pricing model as of the measurement dates

as described in the table below. The Black-Scholes option pricing model uses a consistent set of valuation inputs (including Root’s stock

price, volatility, market risk-free rate, and the options’ strike price and term) which have been updated as of each measurement date, as

applicable. RSU and PSU grant date fair values are determined using the stock price on the date of grant. Adjustments have been made

using the stock price as of the measurement dates as described in the table below.

PEO	2025 ($)	2024 ($)	2023 ($)	2022 ($)	2021 ($)
Summary Compensation Table Total	8,163,348	10,653,120	8,687,806	5,126,730	5,784,695
-SCT “Stock Awards” Column Value	( 5,499,875 )	( 6,504,587 )	( 2,121,471 )	( 2,117,395 )	( 5,066,228 )
-SCT “Option Awards” Column Value	—	—	—	—	—
+year-end fair value of equity awards granted in the covered year that are outstanding and unvested as of the covered year end	3,744,306	6,471,326	2,471,966	276,530	1,539,689
+/-change in fair value (from prior year end to covered year end) of equity awards granted in prior years that are outstanding and unvested as of the covered year end	2,925,933	20,250,158	505,897	( 5,137,824 )	( 24,692,246 )
+vesting date fair value of equity awards granted and vested in the covered year end	—	—	—	—	—
+/- change in fair value (from prior year end to vesting date) of equity awards granted in prior years that vested in the covered year	4,779,552	2,758,811	165,627	( 1,150,606 )	( 2,751,629 )
-fair value as of prior year end of equity awards granted in prior years that failed to vest in the covered year	—	—	—	—	—
+dividends or earnings paid on equity awards in the covered year	—	—	—	—	—
Total Amount Added or Deducted from Summary Compensation Table Total	5,949,916	22,975,708	1,022,019	( 8,129,295 )	( 30,970,414 )
Compensation Actually Paid	14,113,264	33,628,828	9,709,825	( 3,002,565 )	( 25,185,719 )

Average of Non-PEO NEOs	2025 ($)	2024 ($)	2023 ($)	2022 ($)	2021 ($)
Summary Compensation Table Total	4,159,731	5,444,054	3,720,868	5,231,713	9,760,351
-SCT “Stock Awards” Column Value	( 2,908,311 )	( 3,514,939 )	( 1,103,360 )	( 2,630,288 )	( 8,996,668 )
-SCT “Option Awards” Column Value	—	—	—	—	—
+year-end fair value of equity awards granted in the covered year that are outstanding and unvested as of the covered year end	1,979,967	3,377,227	1,283,361	389,979	938,417
+/-change in fair value (from prior year end to covered year end) of equity awards granted in prior years that are outstanding and unvested as of the covered year end	1,812,879	7,626,620	247,426	( 389,707 )	( 1,181,515 )
+vesting date fair value of equity awards granted and vested in the covered year end	—	—	—	—	—
+/- change in fair value (from prior year end to vesting date) of equity awards granted in prior years that vested in the covered year	1,808,501	1,342,928	207,275	( 211,992 )	( 419,568 )
-fair value as of prior year end of equity awards granted in prior years that failed to vest in the covered year	—	—	—	( 777,122 )	( 6,062,096 )
+dividends or earnings paid on equity awards in the covered year	—	—	—	—	—
Total Amount Added or Deducted from Summary Compensation Table Total	2,693,036	8,831,836	634,702	( 3,619,130 )	( 15,721,430 )
Compensation Actually Paid	6,852,767	14,275,890	4,355,570	1,612,583	( 5,961,079 )

(3) Our peer group for the purposes of this disclosure includes Trupanion Inc., Kinsale Capital Group Inc., Lemonade Inc., Goosehead Insurance

Inc., Palomar Holdings Inc. and Kemper Corp, which are the issuers included in the peer group depicted in our performance graph. Total

Stockholder Return for the Company and the peer group was calculated as the yearly percentage change in cumulative Total Stockholder

Return based on a deemed fixed investment of $100 at market close on December 31, 2020 and in accordance with Items 201(e) and 402(v)

of Regulation S-K. Because fiscal years are presented in the table in reverse chronological order (from top to bottom), the table should be

read from bottom to top for purposes of understanding cumulative returns over time.

(4) “Adjusted EBITDA” as defined in the “Compensation Discussion and Analysis— 2025 Annual Cash Incentive Performance Award

Measures” section above.

The following list (the “Tabular List”) provides the performance measures that we believe represent the most

important measures we used to link compensation actually paid to our named executive officers for fiscal year 2025

to our performance:

Tabular List
Adjusted EBITDA	We use Adjusted EBITDA as an internal performance measure in the management of our operations because we believe it provides management and other users of our financial information useful insight into our results of operations and underlying business performance.
Gross Accident Period Loss Ratio	We view gross accident period loss ratio as the best measure of the impact of pricing and underwriting actions.
Policies In Force Growth	We view policies in force as an important metric to assess our financial performance because policy growth drives our revenue growth, expands brand awareness, deepens our market penetration, and generates additional data to continue to improve the functioning of our platform.

Total Stockholder Return (“TSR”) is intended to reflect the change in value of a $100 investment made on

December 31, 2020. Both cumulative TSR and the noted compensation reflect the full period between December 31,

2020 and December 31, 2025 . The chart below demonstrates the relationship between Root’s TSR and

Compensation Actually Paid to Mr. Timm and our Non-PEO NEOs.

The Compensation A ctually Paid to Mr. Timm and our other Non-PEO NEOs is generally correlated with our net

income or loss over the period January 1, 2021 through December 31, 2025 as demonstrated in the chart below.

The Compensation Actually Paid to Mr. Timm and our other Non-PEO NEOs is generally correlated with our

Adjusted EBITDA over the period January 1, 2021 through December 31, 2025 as demonstrated in the chart below.

Policy Regarding Options and Similar Equity Awards

The Company does not currently grant awards of stock options, stock appreciation rights or similar option-like

equity awards . Accordingly, the Company does not have a specific policy or practice on the timing of grants of such

awards in relation to the disclosure of material nonpublic information . In the event the Company determines to grant

awards of stock options or similar equity awards in the future, the compensation committee will evaluate the

appropriate steps to take in relation to the foregoing.

Employee Benefit and Stock Plans

We believe that our ability to grant equity awards is a valuable and necessary compensation tool that aligns the long-

term financial interests of our employees, consultants and directors with the financial interests of our stockholders.

In addition, we believe that our ability to grant RSUs, stock options and other equity-based awards helps us to

attract, retain and motivate employees, consultants and directors and encourages them to devote their best efforts to

our business and financial success. The principal features of our equity incentive plans are summarized below. These

summaries are qualified in their entirety by reference to the actual text of the plans.

2020 Equity Incentive Plan

In October 2020, our board of directors adopted, and our stockholders approved, our 2020 Plan as a successor to our

2015 Equity Incentive Plan (the “2015 Plan”). The 2020 Plan provides for the grant of incentive stock options

(“ISOs”) within the meaning of Section 422 of the Code to employees, including employees of any of our parent or

subsidiary corporations, and for the grant of nonstatutory stock options (“NSOs”), stock appreciation rights,

restricted stock awards, restricted stock unit awards, performance awards and other forms of awards to employees,

directors and consultants, including employees and consultants of our affiliates.

Authorized Shares. The aggregate number of shares of our Class A common stock that may be issued under our

2020 Plan adjusted proportionately following our August 12, 2022, 1-for-18 reverse stock split, was 4,890,299

shares on December 31, 2025 . In addition, the number of shares of our Class A common stock reserved for issuance

under our 2020 Plan automatically increases on January 1 of each year, from January 1, 2021 through January 1,

2030, in an amount equal to (1) 4% of the total number of shares of our common stock (both Class A and Class B)

outstanding on December 31 of the preceding year or (2) a lesser number of shares of our Class A common stock

determined by our board of directors prior to the date of the increase. On January 1, 2026, the total number of shares

available for issuance under the 2020 Plan was increased by 621,626 shares pursuant to this provision. The

maximum number of shares of our Class A common stock that may be issued on the exercise of ISOs under our

2020 Plan following the reverse stock split is 6,666,666 shares .

Corporate Transactions. The following applies to stock awards under the 2020 Plan in the event of a corporate

transaction (as defined in the 2020 Plan), unless otherwise provided in a participant’s stock award agreement or

other written agreement with us or one of our affiliates or unless otherwise expressly provided by the plan

administrator at the time of grant.

In the event of a corporate transaction, any stock awards outstanding under the 2020 Plan may be assumed,

continued or substituted by any surviving or acquiring corporation (or its parent company) and any reacquisition or

repurchase rights held by us with respect to the stock award may be assigned to our successor (or its parent

company). If the surviving or acquiring corporation (or its parent company) does not assume, continue or substitute

such stock awards, then (1) with respect to any such stock awards that are held by participants whose continuous

service has not terminated prior to the effective time of the corporate transaction, or current participants, the vesting

(and exercisability, if applicable) of such stock awards will be accelerated in full (or, in the case of performance

awards with multiple vesting levels depending on the level of performance, vesting will accelerate at 100% of the

target level) to a date prior to the effective time of the corporate transaction (contingent upon the effectiveness of the

corporate transaction) and such stock awards will terminate if not exercised (if applicable) at or prior to the effective

time of the corporate transaction and any reacquisition or repurchase rights held by us with respect to such stock

awards will lapse (contingent upon the effectiveness of the corporate transaction) and (2) any such stock awards that

are held by persons other than current participants will terminate if not exercised (if applicable) prior to the effective

time of the corporate transaction, except that any reacquisition or repurchase rights held by us with respect to such

stock awards will not terminate and may continue to be exercised notwithstanding the corporate transaction.

In the event a stock award will terminate if not exercised prior to the effective time of a corporate transaction, the

plan administrator may provide, in its sole discretion, that the holder of such stock award may not exercise such

stock award but instead will receive a payment equal in value to the excess (if any) of (1) the per share amount

payable to holders of Class A common stock in connection with the corporate transaction, over (2) any per share

exercise price payable by such holder, if applicable. In addition, any escrow, holdback, earn out or similar provisions

in the definitive agreement for the corporate transaction may apply to such payment to the same extent and in the

same manner as such provisions apply to the holders of our Class A common stock.

2020 Employee Stock Purchase Plan

In October 2020, our board of directors adopted, and our stockholders approved, the 2020 Employee Stock Purchase

Plan (“ESPP”). The purpose of the ESPP is to secure the services of new employees, to retain the services of

existing employees and to provide incentives for such individuals to exert maximum efforts toward our success and

that of our affiliates. The ESPP is intended to qualify as an “employee stock purchase plan” within the meaning of

Section 423 of the Code. Employees may have to satisfy one or more of the following service requirements before

participating in the ESPP, as determined by our board of directors, including: (1) being customarily employed for

more than 20 hours per week; (2) being customarily employed for more than five months per calendar year; or (3)

continuous employment with us or one of our affiliates for a period of time (not to exceed two years). No employee

may purchase shares under the ESPP at a rate in excess of $25,000 worth of our Class A common stock based on the

fair market value per share of our Class A common stock at the beginning of an offering for each year such a

purchase right is outstanding. Finally, no employee will be eligible for the grant of any purchase rights under the

ESPP if immediately after such rights are granted, such employee has voting power over 5% or more of our

outstanding capital stock measured by vote or value pursuant to Section 424(d) of the Code.

Share Reserve. The aggregate number of shares of our Class A common stock that may be issued under the ESPP

was 996,930 shares on December 31, 2025 . This includes 277,777 shares of our Class A common stock originally

issuable under the ESPP, adjusted proportionately following our reverse stock split, and annual increases. The

number of shares of our Class A common stock reserved for issuance automatically increases on January 1 of each

year, from January 1, 2021 through January 1, 2030, by the lesser of (1) 1% of the total number of shares of our

common stock (both Class A and Class B) outstanding on December 31 of the preceding calendar year and (2)

416,666 shares of our Class A common stock, except that, prior to the date of any such increase, our board of

directors may determine that such increase will be less than the amount set forth in clauses (1) and (2). On January

1, 2026, the total number of shares available for issuance under the ESPP was increased by 155,406 shares pursuant

to this provision.

Corporate Transactions. In the event of a corporate transaction (as defined in the ESPP), any then-outstanding rights

to purchase our stock under the ESPP may be assumed, continued or substituted by any surviving or acquiring entity

(or its parent company). If the surviving or acquiring entity (or its parent company) elects not to assume, continue or

substitute such purchase rights, then the participants’ accumulated payroll contributions will be used to purchase

shares of our Class A common stock within 10 business days prior to such corporate transaction, and such purchase

rights will terminate immediately.

Amended and Restated 2015 Equity Incentive Plan

In March 2015, the board of directors of our subsidiary Caret Holdings, Inc. adopted, and its stockholders approved,

our 2015 Plan. In August 2019, our board of directors adopted the 2015 Plan and assumed the outstanding

obligations thereunder, such that each outstanding option to purchase shares of the common stock of Caret Holdings,

Inc. was converted into an option to purchase an equal number of shares of our Class B common stock subject to the

same terms and conditions set forth in the 2015 Plan. The 2015 Plan has been periodically amended. The 2015 Plan

provides for the grant of ISOs to our employees and any of our subsidiary corporations’ employees and for the grant

of NSOs, restricted stock awards or restricted stock units to our employees, directors and consultants, and any of our

affiliates’ employees and consultants. The 2015 Plan was terminated in connection with our initial public offering

and no further grants may be made under the 2015 Plan. However, all outstanding stock awards granted under the

2015 Plan continue to be subject to the terms and conditions of the 2015 Plan and the agreements evidencing such

stock awards.

Corporate Transactions. In the event of (1) our dissolution or liquidation or (2) an “acquisition” (as defined in the

2015 Plan), outstanding awards may be assumed, converted or replaced by the successor or acquiring corporation (if

any). In the alternative, the successor or acquiring corporation may substitute equivalent awards or provide

substantially similar consideration to participants as was provided to our stockholders. The successor or acquiring

corporation may also substitute awards by issuing substantially similar shares or other property subject to repurchase

restrictions and other provisions no less favorable to the participant than those which applied immediately prior to

the transaction. If such successor or acquiring corporation (if any) does not assume, convert, replace or substitute

awards, then the vesting of such awards will accelerate and options will become exercisable in full prior to the

consummation of such event, and if such options are not exercised prior to the consummation of the corporate

transaction, they will terminate.

Equity Compensation Plan Information

The following table summarizes our equity compensation plan information as of December 31, 2025 . Information is

included for equity compensation plans approved by our stockholders. We do not have any equity compensation

plans not approved by our stockholders:

Plan Category	Number of securities to be issued upon exercise of outstanding options, warrants and rights (a) (#)	Weighted-average exercise price of outstanding options, warrants and rights (b) ($)	Number of securities remaining available for issuance under equity compensation plans (excluding securities reflected in column (a)) (c) (#)
Equity compensation plans approved by security holders:
2015 Equity Incentive Plan (1)	105,160	34.80	—
2020 Equity Incentive Plan (2)	1,224,988	—	1,800,160
2020 Employee Stock Purchase Plan (3)	—	—	996,930
Equity compensation plans not approved by security holders	—	—	—
Total	1,330,148		2,797,090

(1 ) Following the adoption of the 2020 Plan, no additional stock awards were granted under the 2015 Plan. Any shares becoming available

under the 2015 Plan by repurchase, forfeiture, expiration or cancellation will become available for grant under the 2020 Plan. Column (a)

reflects 105,160 options not forfeited, cancelled or expired as of December 31, 2025 under the 2015 Plan and column (b) reflects the

weighted-average exercise price of the options.

(2) The number of shares of Class A common stock reserved for issuance under the 2020 Plan automatically increases on January 1 of each

year, beginning on January 1, 2021 and continuing through and including January 1, 2030, by 4% of the total number of shares of our

common stock outstanding on December 31 of the preceding calendar year or a lesser number of shares determined by our board of

directors. Pursuant to the terms of the 2020 Plan, an additional 621,626 shares were added to the number of available shares effective

January 1, 2026. Column (a) reflects 570,888 restricted stock units and 654,100 performance-based restricted stock units presented at target

level of performance as of December 31, 2025 under the 2020 Plan. An additional 380,563 performance-based restricted stock units could

vest if maximum performance is achieved. No amount is reported in column (b) as restricted stock units have no exercise price.

(3) The number of shares of Class A common stock reserved for issuance under the ESPP automatically increases on January 1 of each year,

beginning on January 1, 2021 and continuing through and including January 1, 2030, by the lesser of (i) 1% of the total number of shares of

our common stock outstanding on December 31 of the preceding calendar year, (ii) 416,666 shares or (iii) such lesser number of shares

determined by our board of directors. Pursuant to the terms of the ESPP, an additional 155,406 shares were added to the number of available

shares effective January 1, 2026. No shares have been issued under this plan as of December 31, 2025 .

PROPOSAL 3 - APPROVAL, ON AN ADVISORY BASIS,

OF OUR NAMED EXECUTIVE OFFICER COMPENSATION

Pursuant to Section 14A of the Exchange Act, we are conducting an advisory vote to approve the compensation of

our named executive officers as disclosed in this Proxy Statement. At the 2022 Annual Meeting, the stockholders

approved the board of directors’ proposal to seek advisory approvals of the compensation of our named executive

officers on an annual basis. Accordingly, we expect that the next advisory vote, following the vote at the Annual

Meeting, to approve the compensation of our named executive officers will take place at our 2027 Annual Meeting.

Although this vote is nonbinding, the compensation committee values your opinion and expects to consider the

voting results when making future decisions about named executive officer compensation.

Stockholders may also contact management to provide input on named executive officer compensation matters at

any time by contacting Investor Relations, by email at: [email protected].

As described in the “ Compensation Discussion and Analysis ” section of this Proxy Statement, our compensation

committee has effectively established an executive compensation program that reflects both Company and individual

performance. Executive compensation decisions are made in order to attract, motivate, retain and reward talented

executives, with a focus on delivering business results and value to our stockholders.

Our compensation committee consistently exercises care and discipline in determining executive compensation. Our

board of directors urges you to review carefully the “ Compensation Discussion and Analysis ” section that describes

our compensation philosophy and programs in greater detail and to approve the following resolution:

“RESOLVED, that the compensation paid to the Company’s named executive officers, as disclosed pursuant to Item

402 of Regulation S-K, including in the “ Compensation Discussion and Analysis, ” compensation tables and

accompanying narrative discussion, is hereby APPROVED.”

OUR BOARD OF DIRECTORS RECOMMENDS A

VOTE “FOR” THE APPROVAL, ON AN ADVISORY BASIS,

OF OUR NAMED EXECUTIVE OFFICER COMPENSATION.

PROPOSAL 4 - APPROVAL OF AN AMENDMENT TO THE COMPANY’S

AMENDED AND RESTATED CERTIFICATE OF INCORPORATION

TO ALLOW FOR THE EXCULPATION OF CERTAIN OFFICERS

Background

Our Amended and Restated Certificate of Incorporation limits the monetary liability of our directors in certain

circumstances pursuant to, and consistent with, Section 102(b)(7) of the General Corporation Law of the State of

Delaware (the “DGCL”). Effective August 1, 2022, Section 102(b)(7) of the DGCL was amended to permit a

corporation to include in its certificate of incorporation a provision eliminating or limiting monetary liability for

certain officers, in addition to directors, for a breach of the duty of care in certain circumstances. As amended,

Section 102(b)(7) of the DGCL permits exculpation only for direct claims brought by stockholders for breach of

certain officers’ fiduciary duty of care, including class actions, and accordingly would not eliminate officers’

monetary liability for breach of fiduciary duty claims brought by the corporation itself or for derivative claims

brought by stockholders in the name of the corporation. On April 11, 2026, the board of directors unanimously

approved and declared advisable the proposed amendment to our Amended and Restated Certificate of Incorporation

that would eliminate or limit the monetary liability of certain officers to the extent permitted by Section 102(b)(7) of

the DGCL (the “Proposed Amendment”). The Proposed Amendment would not limit the liability of officers for any

breach of the duty of loyalty to us or our stockholders, any acts or omissions not in good faith or which involve

intentional misconduct or a knowing violation of the law, and any transaction from which the officer derived an

improper personal benefit. The rationale for limiting the scope of our officers’ liability, as further described below,

is to strike a balance between stockholders’ interest in accountability and their interest in the Company being able to

recruit and retain quality officers to work on its behalf while also addressing rising litigation and insurance costs.

The board of directors recommends that our stockholders approve and adopt the Proposed Amendment. Upon

approval and adoption of this proposal, the Company will file a Certificate of Amendment to our Amended and

Restated Certificate of Incorporation, in the form attached hereto as Appendix A, with the Secretary of State of the

State of Delaware shortly after the Annual Meeting. The board of directors, in its sole discretion, reserves the right

to abandon the Proposed Amendment at any time before it becomes effective, even if it is approved and adopted by

the stockholders.

Reasons for the Proposed Amendment

Enhanced Ability to Attract and Retain Officers

The board of directors believes that amending our Amended and Restated Certificate of Incorporation to add the

authorized liability protection for certain officers, consistent with the protection in our Amended and Restated

Certificate of Incorporation currently afforded to our directors, is necessary to continue to attract and retain

experienced and qualified officers. In accordance with the DGCL, the Proposed Amendment would only apply to

certain officers, namely to a person who, during the course of conduct alleged to be wrongful, (i) is or was serving as

our CEO, chief operating officer, chief financial officer, chief legal officer, chief accounting officer, controller, or

treasurer, (ii) is or was identified in our public filings with the Securities and Exchange Commission as one of our

most highly compensated executive officers, or (iii) has, by written agreement with the Company, consented to be

identified as an officer for purposes of being subject to personal jurisdiction in Delaware. The Proposed Amendment

would enable our officers to exercise their business judgment in furtherance of our stockholders’ interests without

the potential distraction of risking personal liability. An officer’s role often requires the officer to make decisions on

crucial and time-sensitive matters, which can create substantial risk of investigations, claims, actions, suits, or

proceedings seeking to impose liability based on hindsight, especially in the current litigious environment and

regardless of merit. Further, enhancing our ability to retain and attract experienced officers is in the best interests of

the Company, and we should seek to assure such persons that exculpation under certain circumstances is available.

We believe that failing to adopt the Proposed Amendment could impact our recruitment and retention of exceptional

officer candidates who conclude that the potential exposure to liabilities, costs of defense, and other risks of

proceedings exceeds the benefits of serving as an officer of the Company.

Addressing Rising Litigation and Insurance Costs for Stockholders

Prior to the amendment of Section 102(b)(7) of the DGCL, Delaware law permitted Delaware corporations to

exculpate directors from personal liability for monetary damages associated with breaches of the duty of care, but

that protection did not extend to a Delaware corporation’s officers. Consequently, stockholder plaintiffs have

employed the tactic of bringing certain claims that would otherwise be exculpated if brought against directors

against individual officers to avoid dismissal of such claims. The amendment to Section 102(b)(7) of the DGCL was

adopted to address inconsistent treatment between officers and directors and address rising litigation and insurance

costs for stockholders. Accordingly, the Proposed Amendment will align certain protections for certain of our

officers to those currently available to our directors. Further, the Proposed Amendment will not negatively impact

stockholder rights, considering the narrow class and type of claims for which officers’ liability would be exculpated.

In addition, we are not proposing the Proposed Amendment in anticipation of any specific litigation; rather, we are

proposing the Proposed Amendment on a prospective basis to help mitigate potential future harm to the Company

and its stockholders.

Accordingly, because of the benefits we believe would accrue to us and our stockholders in the form of an enhanced

ability to attract and retain talented officers and to address rising litigation and insurance costs for stockholders, the

board of directors recommends that our stockholders approve and adopt the Proposed Amendment as described

herein.

The approval and adoption of the amendment to our Amended and Restated Certificate of Incorporation requires the

affirmative vote of the holders of at least 66 2/3% of the shares outstanding and entitled to vote at the Annual

Meeting.

OUR BOARD OF DIRECTORS RECOMMENDS A VOTE “FOR” THE

APPROVAL OF AN AMENDMENT TO THE COMPANY’S AMENDED

AND RESTATED CERTIFICATE OF INCORPORATION, AS AMENDED,

TO ALLOW FOR EXCULPATION OF CERTAIN OFFICERS.

SECURITY OWNERSHIP OF

CERTAIN BENEFICIAL OWNERS AND MANAGEMENT

The following table sets forth certain information regarding the ownership of our Class A and Class B common

stock as of April 6, 2026 , by:

• each person or entity known by us to be beneficial owners of more than five percent of our Class A common

stock or Class B common stock;

• each of our named executive officers;

• each of our directors; and

• all of our current executive officers and directors as a group.

We have determined beneficial ownership in accordance with the rules and regulations of the SEC and the

information set forth below is not necessarily indicative of beneficial ownership for any other purpose. Except as

indicated by the footnotes below, we believe, based on information furnished to us, that the persons and entities

named in the table below have sole voting and sole investment power with respect to all shares that they beneficially

own, subject to applicable community property laws.

Applicable percentage ownership is based o n 14,015,900 shares of Class A common stock and 1,806,236 shares of

Class B common stock outstanding as of April 6, 2026 , and 14,053,096 shares of Series A preferred stock

outstanding as of April 6, 2026 and entitled to 780,727 votes. In computing the number of shares beneficially owned

by a person and the percentage ownership of such person, we deemed to be outstanding all shares subject to options

held by the person that are currently exercisable, or exercisable or would vest based on service-based vesting

conditions within 60 days of April 6, 2026 . In addition, we deemed to be outstanding all RSUs held by the person

that would vest based on service-based vesting conditions within 60 days of April 6, 2026 . However, except as

described above, we did not deem such shares outstanding for the purpose of computing the percentage ownership of

any other person.

Unless otherwise indicated, the address for each beneficial owner listed in the table below is c/o Root, Inc., 80 E.

Rich Street, Suite 500, Columbus, Ohio 43215.

	Beneficial Ownership — Class A Common Stock		Class B Common Stock		% of Total Voting Power†
Beneficial Owner	Number of Shares	%	Number of Shares	%
5% Stockholders:
Entities associated with Ribbit Capital (1) .......................	503,800	3.6 %	728,807	40.3 %	23.7 %
Carvana Group, LLC (2) ..................................................	780,727	5.6 %	—	—	2.4 %
Directors and Named Executive Officers:
Alexander Timm (3) .........................................................	144,766	1.0 %	1,067,184	59.1 %	32.9 %
Mahtiyar Bonakdarpour (4) ..............................................	413,459	2.9 %	15,392	*	1.7 %
Jonathan Allison (5) .........................................................	14,042	*	12,024	*	*
Megan Binkley (6) ...........................................................	52,321	*	2,638	*	*
Douglas Ulman (7) ...........................................................	44,549	*	—	—	*
Jerri DeVard (8) ...............................................................	18,532	*	—	—	*
Lawrence Hilsheimer (9) ..................................................	42,591	*	5,555	*	*
Nancy Kramer (10) ...........................................................	27,933	*	4,166	*	*
Beth Birnbaum (11) ..........................................................	14,280	*	—	—	*
Julie Szudarek (12) ...........................................................	11,832	*	—	—	*
Donna Dorsey (13) ............................................................	9,956	*	—	—	*
All executive officers and directors as a group (11 persons) ...................................................................	794,261	5.7 %	1,106,959	61.3 %	36.1 %

Less than one percent.

† Percentage of total voting power represents voting power with respect to all shares of our Class A common stock, Class B common stock

and Series A preferred stock as a single class. The holders of our Class B common stock are entitled to 10 votes per share and holders of our

Class A common stock are entitled to one vote per share. The holder of the Series A preferred stock is entitled to vote with the holders of

Class A common stock and has the right to one vote per share of Class A common stock into which the Series A preferred stock is

convertible.

(1) Based on the information contained in the Schedule 13G/A filed on August 14, 2025. Consists of 728,807 shares of Class B common stock

held by Ribbit Capital IV, L.P,. for itself and as nominee for Ribbit Founder Fund IV, L.P. (“Ribbit Capital IV”), and RT-E Ribbit

Opportunity IV, LLC (“Ribbit RT-E”). Meyer Malka is the sole director of Ribbit Capital GP IV, Ltd., which is the general partner of Ribbit

Capital GP IV, L.P., which is both the general partner of Ribbit Capital IV and the managing member of Ribbit RT-E and as such, Mr.

Malka may be deemed to hold voting and investment power with respect to the shares held by Ribbit Capital IV and Ribbit RT-E. The

principal office address of each of these entities is c/o Ribbit Capital Management, 364 University Avenue, Palo Alto, California 94301.

(2) Based on the information contained in the Schedule 13D/A filed on March 3, 2026. Consists of 780,727 shares of Class A common stock

into which Series A preferred stock is convertible at the option of the holder, subject to such holder’s receipt of approval from the

Company’s domestic insurance regulators in the event such conversion would cause the holder to hold in excess of 9.9% of the voting stock

of the Company. Excludes 2,927,727 shares of Class A Common Stock issuable upon the exercise of exercisable warrants that were out of

the money as of April 6, 2026, and for which the Company has the option to net settle. The principal office address of Carvana Group, LLC

is 300 E. Rio Salado Parkway, Tempe, Arizona 85281.

(3) Consists of (i) 144,766 shares of Class A common stock, (ii) 1,056,393 shares of Class B common stock, of which 6,044 shares may be

repurchased by us at the original purchase price as of April 6, 2026, and (iii) 10,791 shares of Class B common stock held by the Timm

Descendants Trust. The Timm Descendants Trust is a trust for the benefit of Mr. Timm and his immediate family.

(4) Consists of (i) 264,165 shares of Class A common stock, and (ii) 15,392 shares of Class B common stock issuable to Mr. Bonakdarpour

pursuant to exercisable options. Also includes the following shares over which Mr. Bonakdarpour may be deemed to have an indirect

pecuniary interest through his spouse’s carried interest in Drive Capital Overdrive Fund I (GP), LLC, (iii) 99,687 shares of Class A common

stock held by Drive Capital Overdrive Fund I, L.P., (iv) 48,201 shares of Class A common stock held by Drive Capital Overdrive Fund I

(TE), L.P., and (v) 1,406 shares of Class A common stock held by Drive Capital Overdrive Ignition Fund I, L.P (collectively, the “Drive

shares”). Neither Mr. Bonakdarpour nor his spouse has voting or investment control over the Drive shares.

(5) Consists of (i) 14,042 shares of Class A common stock, and (ii) 12,024 shares of Class B common stock issuable to Mr. Allison pursuant to

exercisable options.

(6) Consists of (i) 52,321 shares of Class A common stock, (ii) 1,111 shares of Class B common stock, and (iii) 1,527 shares of Class B

common stock issuable to Ms. Binkley pursuant to exercisable options.

(7) Consists of (i) 33,824 shares of Class A common stock held by the Douglas E. Ulman 2016 Revocable Trust, (ii) 9,606 shares of Class A

common stock held by the Douglas E. Ulman 2016 Irrevocable Trust for which Mr. Ulman’s spouse is the trustee, and (iii) 1,119 shares of

Class A common stock issuable in respect of restricted stock units vesting within 60 days of April 6, 2026 and upon retirement from service

on the board of directors. In addition, Mr. Ulman has sole voting control over 3,755 shares of Class A common stock in a donor advised

fund.

(8) Consists of (i) 17,413 shares of Class A common stock, and (ii) 1,119 shares of Class A common stock issuable in respect of restricted stock

units vesting within 60 days of April 6, 2026 and upon retirement from service on the board of directors.

(9) Consists of (i) 41,472 shares of Class A common stock, 1,596 of which are held through Mr. Hilsheimer’s IRA, (ii) 1,119 shares of Class A

common stock issuable in respect of restricted stock units vesting within 60 days of April 6, 2026, and (iii) 5,555 shares of Class B common

stock.

(10) Consists of (i) 26,814 shares of Class A common stock, 10,317 of which are held through the Nancy J. Kramer Revocable Trust (ii) 1,119

shares of Class A common stock issuable in respect of restricted stock units vesting within 60 days of April 6, 2026 and upon retirement

from service on the board of directors, and (iii) 4,166 shares of Class B common stock issuable to Ms. Kramer pursuant to exercisable

options.

(11) Consists of (i) 13,161 shares of Class A common stock, and (ii) 1,119 shares of Class A common stock issuable in respect of restricted stock

units vesting within 60 days of April 6, 2026 and upon retirement from service on the board of directors.

(12) Consists of (i) 10,713 shares of Class A common stock, and (ii) 1,119 shares of Class A common stock issuable in respect of restricted stock

units vesting within 60 days of April 6, 2026 and upon retirement from service on the board of directors.

(13) Consists of (i) 8,837 shares of Class A common stock, and (ii) 1,119 shares of Class A common stock issuable in respect of restricted stock

units vesting within 60 days of April 6, 2026 and upon retirement from service on the board of directors.

TRANSACTIONS WITH RELATED PERSONS

The following is a summary of transactions since January 1, 2025 , to which we were a party or will be a party, in

which:

• the amounts involved exceeded or will exceed $120,000; and

• any of our directors, executive officers or holders of more than 5% of Class A common stock or Class B common stock, or any member of the immediate family of, or person sharing the household with, the foregoing persons, had or will have a direct or indirect material interest.

Investors’ Rights Agreement

We are party to an amended and restated investors’ rights agreement (“IRA”) with certain holders of our capital

stock, including entities affiliated with Ribbit Capital, as well as other holders of our previously issued redeemable

convertible preferred stock, all shares of which were converted into shares of our Class B common stock at the time

of our initial public offering. The IRA provides the holders of such shares with certain registration rights, including

the right to demand that we file a registration statement or request that their shares be covered by a registration

statement that we are otherwise filing.

Carvana Agreements

We are a party to an investment agreement and a commercial agreement with, and have issued warrants to, Carvana

Group, LLC (“Carvana”). Pursuant to the investment agreement, Carvana is entitled to certain governance, consent

and registration rights contemplated by the investment agreement. Carvana’s governance rights include the right to

appoint Ernest Garcia III, the President and Chief Executive Officer of Carvana, to our board of directors. Carvana

will no longer be entitled to appoint Mr. Garcia to our board of directors if Carvana ceases to beneficially own any

of the Series A preferred stock acquired by Carvana at the closing of the investment. Carvana has not exercised its

appointment right as of the date hereof. Carvana is subject to customary standstill and non-transfer restrictions in

respect of the Series A preferred stock and the warrants for a five-year period following the closing of the

investment, subject to certain limited exceptions in the investment agreement. Carvana has also covenanted in the

investment agreement to make all required insurance regulatory filings with Root’s domestic insurance regulators in

the event that the conversion of the Series A preferred stock or exercise of the warrants would cause Carvana to hold

in excess of 9.9% of the outstanding voting stock of Root. Both Carvana and Root must use commercially

reasonable efforts to obtain any required regulatory approvals. Carvana has also agreed to vote its shares of Series A

preferred stock at the Annual Meeting in support of Proposal 1 and in the same proportion as our unaffiliated

stockholders with respect to all of the other proposals. Our “unaffiliated stockholders” do not include any of our

current officers and directors and any other beneficial owner of more than 5.0% (determined on a fully-diluted basis)

of our outstanding common stock (other than investors that are eligible to file a Schedule 13G with the SEC

pursuant to Rule 13d-1(b) of the Exchange Act) and any affiliate of any of the foregoing persons.

Policies and Procedures for Transactions with Related Persons

We have adopted a written policy that our executive officers, directors, nominees for election as a director,

beneficial owners of more than 5% of any class of our common stock and any members of the immediate family of

any of the foregoing persons are not permitted to enter into a related person transaction with us without the approval

or ratification of our board of directors or our audit, risk and finance committee. Any request for us to enter into a

transaction with an executive officer, director, nominee for election as a director, beneficial owner of more than 5%

of any class of our common stock or any member of the immediate family of any of the foregoing persons, in which

the amount involved exceeds $120,000 and such person would have a direct or indirect interest, must be presented to

our board of directors or our audit, risk and finance committee for review, consideration and approval. In approving

or rejecting any such proposal, our board of directors or our audit, risk and finance committee is to consider the

material facts of the transaction, including whether the transaction is on terms no less favorable than terms generally

available to an unaffiliated third party under the same or similar circumstances and the extent of the related person’s

interest in the transaction.

DELINQUENT SECTION 16(a) REPORTS

Section 16(a) of the Exchange Act requires directors, executive officers and beneficial owners of more than 10

percent of our equity securities to file reports of holdings and transactions in its equity securities with the SEC and

Nasdaq generally within two business days of a reportable transaction. We seek to assist our directors and executive

officers by monitoring transactions and completing and filing reports on their behalf. Based solely on our review of

Section 16 reports prepared by or furnished to us, we believe that all Section 16(a) SEC filing requirements

applicable to our directors and executive officers and beneficial owners of more than 10 percent of our equity

securities for fiscal year ended December 31, 2025 were timely met, except as follows: a Form 4 reporting one

transaction for Ms. Kramer was filed one day late due to inability to access Ms. Kramer’s EDGAR filing codes.

HOUSEHOLDING OF PROXY MATERIALS

The SEC has adopted rules that permit companies and intermediaries (e.g., brokers) to satisfy the delivery

requirements for Notices of Internet Availability of Proxy Materials or other Annual Meeting materials with respect

to two or more stockholders sharing the same address by delivering a single Notice of Internet Availability of Proxy

Materials or other Annual Meeting materials addressed to those stockholders. This process, which is commonly

referred to as “householding,” potentially means extra convenience for stockholders and cost savings for companies.

This year, a number of brokers with account holders who are our stockholders will likely be “householding” our

proxy materials. A single Notice of Internet Availability of Proxy Materials will be delivered to multiple

stockholders sharing an address unless contrary instructions have been received from the affected stockholders.

Once you have received notice from your broker that they will be “householding” communications to your address,

“householding” will continue until you are notified otherwise or until you revoke your consent. If, at any time, you

no longer wish to participate in “householding” and would prefer to receive a separate Notice of Internet

Availability of Proxy Materials, please notify your broker or us. Direct your written request to us via email at

[email protected] or via mail to Root, Inc., 80 E. Rich Street, Suite 500, Columbus, Ohio 43215, Attention:

Secretary, or you may make a request by telephone to (866) 980-9431. Stockholders who currently receive multiple

copies of the Notices of Internet Availability of Proxy Materials at their addresses and would like to request

“householding” of their communications should contact their brokers.

OTHER MATTERS

Our board of directors knows of no other matters that will be presented for consideration at the Annual Meeting

except as indicated in the notice. However, if any other matters are properly brought before the Annual Meeting for

action of which we did not have notice on or prior to March 6, 2026, or that applicable laws otherwise permit

proxies to vote on a discretionary basis, it is the intention of the persons named in the accompanying proxy to vote

on such matters in accordance with their best judgment.

By Order of the Board of Directors,

Jodi E. Baker

Chief Legal Officer and Secretary

April 24, 2026

We have filed our Annual Report on Form 10-K for the fiscal year ended December 31, 2025 , with the SEC. It is

available free of charge at the SEC’s web site at www.sec.gov. Stockholders can also access this Proxy Statement

and our Annual Report on Form 10-K at ir.joinroot.com. A copy of our Annual Report on Form 10-K for the fiscal

year ended December 31, 2025 , is also available without charge upon written request to us via email at

[email protected] .

A-1

APPENDIX A

CERTIFICATE OF AMENDMENT

AMENDED AND RESTATED CERTIFICATE OF INCORPORATION

ROOT, INC.

Root, Inc., a corporation organized and existing under the General Corporation Law of the State of Delaware

(the “Company”), hereby certifies as follows:

FIRST: That the Board of Directors of the Company has duly adopted resolutions (i) authorizing the Company

to execute and file with the Secretary of State of the State of Delaware this Certificate of Amendment to Amended

and Restated Certificate of Incorporation (this “Second Amendment”) to allow for the exculpation of certain officers

and (ii) declaring this Second Amendment to be advisable, submitted to and considered by the stockholders of the

Company entitled to vote thereon for approval by the affirmative vote of such stockholders in accordance with the

terms of the Company’s Amended and Restated Certificate of Incorporation (the “Certificate of Incorporation”) and

Section 242 of the General Corporation Law of the State of Delaware (the “DGCL”) and recommended for approval

by the stockholders of the Company.

SECOND: That this Second Amendment was duly adopted in accordance with the terms of the Certificate of

Incorporation and the provisions of Section 242 of the DGCL by the Board of Directors and stockholders of the

Company.

THIRD: Immediately upon filing of this Second Amendment, Section A of Article VI of the Certificate of

Incorporation is hereby amended to read in its entirety as follows:

“A. The liability of the directors and officers of the Company for monetary damages for breach of fiduciary

duty as a director or officer shall be eliminated to the fullest extent permitted under applicable law now or as

hereafter amended. Solely for the purpose of this Section A of Article VI, “officer” shall have the meaning provided

in Section 102(b)(7) of the DGCL as currently in effect and as it may hereafter be amended .”

IN WITNESS WHEREOF, the Company has caused this Certificate of Amendment to Amended and Restated

Certificate of Incorporation to be executed by [ ] its [ ], this [ ] day of

[ ], 202[ ].

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Root, Inc. Proxy Solicitation & Information Statement 2026

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Root, Inc. — Proxy Solicitation & Information Statement 2026

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Root, Inc. Proxy Solicitation & Information Statement 2026