[Form 4] UPWORK, INC Insider Trading Activity

Rhea-AI Filing Summary

Hayden Brown, President & CEO and Director of Upwork, Inc. (UPWK), reported multiple stock transactions in mid-September 2025. The Form 4 shows Rule 10b5-1 plan sales and vesting of restricted stock units (RSUs). On 09/17/2025 she sold 20,000 shares at $18. On 09/18/2025 she sold 20,000 shares at $19 and sold 22,344 shares at a weighted-average $19.1639 after receiving 17,734 and 28,677 vested RSUs that same day. On 09/19/2025 she sold another 20,000 shares at $20. After these transactions, she beneficially owned 1,082,358 shares. The filer adopted the 10b5-1 plan on December 6, 2024, and some sales were "sell to cover" for tax withholding in connection with RSU vesting.

Positive

• Transactions were executed under a documented Rule 10b5-1 plan adopted on December 6, 2024, indicating pre-planned, compliant trading.
• RSU vesting was disclosed with 17,734 and 28,677 RSUs recorded as acquired on 09/18/2025, reflecting standard equity compensation realization.

Negative

• Insider sales totaling 82,344 shares across 09/17–09/19/2025 (excluding shares sold to cover taxes) represent notable insider liquidity during the period.
• Sell-to-cover sales occurred to satisfy tax withholding obligations, reducing the reporting person's net holdings despite RSU vesting.

Insights

Corporate Governance Expert

TL;DR: Multiple scheduled insider sales and RSU vesting under a pre-established 10b5-1 plan; routine governance disclosure.

The filings show the CEO/Director engaged in planned disposals under a Rule 10b5-1 plan adopted 12/06/2024 and routine settlement of RSU tax withholding via "sell to cover." Transactions include sales on 09/17–09/19/2025 and RSU vesting on 09/18/2025. From a governance perspective, the presence of a documented trading plan and use of issuer-mandated sell-to-cover mechanics indicate procedural compliance and reduce appearance-based insider trading concerns. Materiality is limited to share count movements and standard equity compensation mechanics.

Securities Analyst

TL;DR: Insider sold shares across several days at prices between $18 and $20; net beneficial holdings remained above one million shares.

The reported sales: 20,000 shares at $18 (09/17), 20,000 at $19 (09/18), 22,344 at a weighted $19.1639 (09/18), and 20,000 at $20 (09/19). Concurrently, RSUs totaling 46,411 shares vested and were recorded as acquired on 09/18. After these actions the reporting person held 1,082,358 shares. For investors, this is a disclosure of insider liquidity events and compensation settlement rather than an operational update. Impact appears neutral absent additional context.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

X

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Brown Hayden

(Last) (First) (Middle)

C/O UPWORK INC.

530 LYTTON AVENUE, SUITE 301

(Street)

PALO ALTO CA 94301

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
UPWORK, INC [ UPWK ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President & CEO

3. Date of Earliest Transaction (Month/Day/Year)
09/17/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	09/17/2025		S(1)		20,000	D	$18	1,098,291	D
Common Stock	09/18/2025		S(1)		20,000	D	$19	1,078,291	D
Common Stock	09/18/2025		M		17,734	A	(2)	1,096,025	D
Common Stock	09/18/2025		M		28,677	A	(2)	1,124,702	D
Common Stock	09/18/2025		S(3)		22,344	D	$19.1639(4)	1,102,358	D
Common Stock	09/19/2025		S(1)		20,000	D	$20	1,082,358	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Restricted Stock Unit	(2)	09/18/2025		M			17,734	(5)	(5)	Common Stock	17,734	$0.00	177,332	D
Restricted Stock Unit	(2)	09/18/2025		M			28,677	(6)	(6)	Common Stock	28,677	$0.00	401,485	D

Explanation of Responses:

1. This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on December 6, 2024.

2. Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.

3. 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.

4. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $18.89 to $19.495 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.

5. 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.

6. 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.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	09/19/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What insider transactions did UPWK CEO Hayden Brown report in September 2025?

Hayden Brown reported sales of 20,000 shares on 09/17/2025 at $18, 20,000 shares on 09/18/2025 at $19, 22,344 shares on 09/18/2025 at a weighted-average $19.1639, and 20,000 shares on 09/19/2025 at $20.

Did Hayden Brown receive any equity awards that vested?

Yes. Two RSU groups vested on 09/18/2025: 17,734 RSUs and 28,677 RSUs, each representing one share per RSU.

Were the sales part of a pre-existing trading plan?

Yes. The Form 4 states the transactions were effected pursuant to a Rule 10b5-1 plan adopted on December 6, 2024.

What was Hayden Brown's beneficial ownership after these transactions?

Following the reported transactions, the filing shows beneficial ownership of 1,082,358 shares.

What does 'sell to cover' mean in this filing?

It indicates shares were sold to satisfy tax withholding obligations tied to RSU vesting; the filing notes these sales do not represent discretionary trades by the reporting person.