Dave Bottoms - 18 Jun 2025 Form 4 Insider Report for UPWORK, INC (UPWK)

Role: GM, Marketplace
Signature: /s/ Jacob McQuown, Attorney-in-Fact
Issuer symbol: UPWK
Transactions as of: 18 Jun 2025
Net transactions value: -$156,149
Form type: 4
Filing time: 23 Jun 2025, 19:22:46 UTC
Previous filing: 22 May 2025
Next filing: 12 Aug 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Bottoms Dave	GM, Marketplace	C/O UPWORK INC., 530 LYTTON AVENUE, SUITE 301, PALO ALTO	/s/ Jacob McQuown, Attorney-in-Fact	23 Jun 2025	0002019194

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPWK	Common Stock	Options Exercise		+8,980			8,980	18 Jun 2025	Direct	F1
transaction	UPWK	Common Stock	Options Exercise		+6,023	+67%		15,003	18 Jun 2025	Direct	F1
transaction	UPWK	Common Stock	Options Exercise		+5,904	+39%		20,907	18 Jun 2025	Direct	F1
transaction	UPWK	Common Stock	Sale	$156,149	-11,562	-55%	$13.51	9,345	18 Jun 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	-8,980	-17%	$0.000000	44,900	18 Jun 2025	Common Stock	8,980		Direct	F1, F4
transaction	UPWK	Restricted Stock Units	Options Exercise	$0	-6,023	-8.3%	$0.000000	66,259	18 Jun 2025	Common Stock	6,023		Direct	F1, F5
transaction	UPWK	Restricted Stock Units	Options Exercise	$0	-5,904	-6.2%	$0.000000	88,562	18 Jun 2025	Common Stock	5,904		Direct	F1, F6

* 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 $13.24 to $13.73 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 December 18, 2022, 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, 2024, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
F6	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.