Erica Gessert - Nov 18, 2025 Form 4 Insider Report for UPWORK, INC (UPWK)

Role: Chief Financial Officer
Signature: /s/ Jacob McQuown, Attorney-in-Fact
Stock symbol: UPWK
Transactions as of: Nov 18, 2025
Transactions value $: -$308,840
Form type: 4
Date filed: 11/20/2025, 06:18 PM
Previous filing: Sep 22, 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Gessert Erica	Chief Financial Officer	C/O UPWORK INC., 530 LYTTON AVENUE, SUITE 301, PALO ALTO	/s/ Jacob McQuown, Attorney-in-Fact	2025-11-20	0001975669

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPWK	Common Stock	Options Exercise		+37.5K	+17.15%		256K	Nov 18, 2025	Direct	F1
transaction	UPWK	Common Stock	Sale	-$146K	-9.06K	-3.54%	$16.14	247K	Nov 18, 2025	Direct	F2, F3
transaction	UPWK	Common Stock	Sale	-$163K	-9.43K	-3.82%	$17.24	238K	Nov 18, 2025	Direct	F2, F4

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	UPWK	Restricted Stock Units	Options Exercise	$0	-37.5K	-14.29%	$0.00	225K	Nov 18, 2025	Common Stock	37.5K		Direct	F1, F5

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
F2	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.
F3	The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.66 to $16.65 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 $16.67 to $17.4932 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.