UPWORK, INC — Director's Dealing 2025

May 20, 2025

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: UPWORK, INC (UPWK)
CIK: 0001627475
Period of Report: 2025-05-18

Reporting Person: Gessert Erica (N/A)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2025-05-18	Common Stock	M	37500.00	—	Acquired	201550.00	Direct
2025-05-19	Common Stock	S	19677.00	$16.5626	Disposed	181873.00	Direct

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2025-05-18	Restricted Stock Units	$	M	37500.00	Disposed		Common Stock (37500.00)	Direct

Footnotes

F1: Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.

F2: Reflects 3,105 shares acquired under the Issuer's employee stock purchase plan on May 14, 2025

F3: Represents the number of shares required to be sold by the Reporting Person to cover tax withholding obligations in connection with the vesting of the RSUs listed in Table II. This sale is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of tax withholding obligations to be funded by a "sell to cover" transaction and does not represent a discretionary trade by the Reporting Person.

F4: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $16.5003 to $16.8929 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or the staff of the Securities and Exchange Commission, upon written request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.

F5: The RSUs vest 25% on May 18, 2024 and then 1/16th of the total number of shares on each quarterly anniversary thereafter, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.