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

Role: Chief Financial Officer
Signature: /s/ Jacob McQuown, Attorney-in-Fact
Issuer symbol: UPWK
Transactions as of: 18 May 2025
Net transactions value: -$325,902
Form type: 4
Filing time: 19 May 2025, 21:40:54 UTC
Previous filing: 20 Mar 2025
Next filing: 23 Jun 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	19 May 2025	0001975669

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPWK	Common Stock	Options Exercise		+37,500	+23%		201,550	18 May 2025	Direct	F1, F2
transaction	UPWK	Common Stock	Sale	$325,902	-19,677	-9.8%	$16.56	181,873	19 May 2025	Direct	F3, 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	-37,500	-11%	$0.000000	300,000	18 May 2025	Common Stock	37,500		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	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.