[Form 4] Upwork Inc. Insider Trading Activity

Rhea-AI Filing Summary

Upwork Inc. director and President & CEO Hayden Brown reported multiple transactions in August 2025 that changed her beneficial ownership of Upwork (UPWK) common stock. On August 15, 2025 she sold 60,000 shares under a Rule 10b5-1 plan at a weighted-average price of $13.7575, leaving her with 1,093,485 shares. Between August 18, 2025 transfers and vesting converted RSUs into shares, adding a total of 50,383 shares, and a "sell to cover" sale of 25,577 shares occurred to satisfy tax withholding at a weighted-average price of $13.8352. After these events her reported beneficial ownership is 1,118,291 shares. Several RSU awards remain subject to future vesting schedules.

Positive

• Use of Rule 10b5-1 plan for the 60,000-share sale, indicating the transaction was pre-established and not opportunistic
• Continued substantial ownership: the reporting person still beneficially owns 1,118,291 shares after transactions
• RSU vesting disclosed with clear schedules, showing alignment with long-term compensation structures

Negative

• Insider sold 85,577 shares total (60,000 under 10b5-1 and 25,577 sell-to-cover), reducing reported holdings
• Weighted-average sale prices of $13.7575 and $13.8352 indicate dispositions near mid-$13 per share range

Insights

Securities Analyst

TL;DR: Insider sold shares under a pre-established 10b5-1 plan and sold shares to cover taxes after RSU vesting; overall holding remains over one million shares.

The transactions include a planned sale of 60,000 shares under a Rule 10b5-1 plan and a mandatory "sell to cover" of 25,577 shares tied to RSU vesting. The RSU vesting converted 50,383 units into common stock, increasing share count before withholding. The use of a 10b5-1 plan indicates the large sale was prearranged and not an ad hoc disposition. Net change reduces reported beneficial ownership from the pre-sale level but leaves the reporting person with a substantial stake of 1,118,291 shares.

Corporate Governance Expert

TL;DR: Transactions appear procedural and governance-compliant: planned trading and mandatory tax-withholding sales after RSU vesting.

The filing documents compliance with Rule 10b5-1 and issuer-mandated "sell to cover" for tax withholding, which are standard mechanisms to manage insider liquidity and tax obligations. Multiple RSU schedules are disclosed with vesting timelines, showing continued alignment with long-term incentive structures. No indication of unusual or opportunistic trades beyond the pre-arranged plan and mandatory withholding.

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)
08/15/2025

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	08/15/2025		S(1)		60,000	D	$13.7575(2)	1,093,485	D
Common Stock	08/18/2025		M		9,589	A	(3)	1,103,074	D
Common Stock	08/18/2025		M		7,610	A	(3)	1,110,684	D
Common Stock	08/18/2025		M		14,850	A	(3)	1,125,534	D
Common Stock	08/18/2025		M		18,334	A	(3)	1,143,868	D
Common Stock	08/18/2025		S(4)		25,577	D	$13.8352(5)	1,118,291	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	(3)	08/18/2025		M			9,589	(6)	(6)	Common Stock	9,589	$0.00	19,178	D
Restricted Stock Unit	(3)	08/18/2025		M			7,610	(7)	(7)	Common Stock	7,610	$0.00	15,221	D
Restricted Stock Unit	(3)	08/18/2025		M			14,850	(8)	(8)	Common Stock	14,850	$0.00	89,100	D
Restricted Stock Unit	(3)	08/18/2025		M			18,334	(9)	(9)	Common Stock	18,334	$0.00	110,000	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. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $13.64 to $14.01 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.

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

4. 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.

5. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $13.74 to $13.987 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.

6. The RSUs vest 25% on February 18, 2023, and then 6.25% of the total shares vest on each quarterly anniversary thereafter, subject to the Reporting Person's continued employment with the Issuer on each vesting date.

7. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2022, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

8. The RSUs vest 25% on February 18, 2024, and then 6.25% of the total shares vest on each quarterly anniversary thereafter, subject to the Reporting Person's continued employment with the Issuer on each vesting date.

9. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	08/19/2025
	** 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 Hayden Brown report for UPWK in August 2025?

Hayden Brown sold 60,000 shares25,577 shares

How many UPWK shares does Hayden Brown beneficially own after these transactions?

1,118,291 shares

Were the sales discretionary or pre-planned?

The 60,000-share sale was executed pursuant to a Rule 10b5-1 plan

What prices were reported for the share sales?

Weighted-average prices

Did any RSUs vest, and how many shares resulted?

RSU vesting on 08/18/2025 converted 50,383 RSUs