Erica Gessert - Mar 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: Mar 18, 2025
Transactions value $: -$56,405
Form type: 4
Date filed: 3/20/2025, 07:01 PM
Previous filing: Feb 20, 2025
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPWK	Common Stock	Options Exercise		+8.43K	+5.38%		165K	Mar 18, 2025	Direct	F1
transaction	UPWK	Common Stock	Sale	-$56.4K	-4.32K	-2.61%	$13.07	161K	Mar 18, 2025	Direct	F2, F3

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	-8.43K	-7.69%	$0.00	101K	Mar 18, 2025	Common Stock	8.43K		Direct	F1, F4
transaction	UPWK	Restricted Stock Units	Award	$0	+155K		$0.00	155K	Mar 18, 2025	Common Stock	155K		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 $12.895 to $13.245 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 RSUs vest in equal quarterly installments over four years beginning on June 18, 2024, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
F5	The RSUs vest in equal quarterly installments over four years beginning on June 18, 2025, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.