UPWORK, INC — Director's Dealing 2021

Mar 9, 2021

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: Upwork Inc. (UPWK)
CIK: 0001627475
Period of Report: 2021-03-04

Reporting Person: Brown Hayden (Director, President & CEO)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2021-03-04	Common Sock	M	2501	$3.67	Acquired	441405	Direct
2021-03-04	Common Sock	M	76755	$3.58	Acquired	518160	Direct
2021-03-04	Common Sock	M	3333	$3.03	Acquired	521493	Direct
2021-03-04	Common Sock	M	177411	$3.68	Acquired	698904	Direct
2021-03-04	Common Sock	S	15504	$42.4661	Disposed	683400	Direct
2021-03-04	Common Sock	S	79418	$43.5098	Disposed	603982	Direct
2021-03-04	Common Sock	S	38759	$44.4135	Disposed	565223	Direct
2021-03-04	Common Sock	S	97756	$45.1926	Disposed	467467	Direct
2021-03-04	Common Sock	S	28563	$46.0699	Disposed	438904	Direct

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2021-03-04	Employee Stock Option (right to buy)	$3.67	M	2501	Disposed	2024-12-18	Common Stock (2501)	Direct
2021-03-04	Employee Stock Option (right to buy)	$3.58	M	76755	Disposed	2025-04-22	Common Sock (76755)	Direct
2021-03-04	Employee Stock Option (right to buy)	$3.03	M	3333	Disposed	2025-12-22	Common Sock (3333)	Direct
2021-03-04	Employee Stock Option (right to buy)	$3.68	M	177411	Disposed	2027-09-25	Common Sock (177411)	Direct

Footnotes

F1: This transaction was effected pursuant to a Rule 10b5-1 trading plan previously adopted by the Reporting Person.

F2: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $41.88 to $42.875 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.

F3: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $42.88 to $43.87 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.

F4: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $43.88 to $44.875 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $44.88 to $45.87 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.

F6: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $45.88 to $46.46 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.

F7: The options vested with respect to 1/60th of the total shares on January 19, 2015, and then 1/60th of the total shares vest monthly thereafter, subject to the continuing employment of the Reporting Person on each vesting date.

F8: The options vested with respect of 1/60th of the total shares on May 15, 2015, and then 1/60th of the total shares vest monthly thereafter, subject to the continuing employment of the Reporting Person on each vesting date. The stock option contains an early-exercise provision and is exercisable as to unvested shares, subject to the Issuer's right of repurchase.

F9: The options vested with respect of 1/60th of the total shares on February 1, 2016, and then 1/60th of the total shares vest monthly thereafter, subject to the continuing employment of the Reporting Person on each vesting date.

F10: The options vested with respect to 1/60th of the total shares on October 26, 2017, and then 1/60th of the total shares vest monthly thereafter, subject to the continuing employment of the Reporting Person on each vesting date.