Upwork CEO Sells $320K in Stock for Tax Obligations, Retains 1.1M Shares

Accepted by SEC EDGAR 06/23/2025 - 07:23 PM EDT Learn about SEC filing dates

Rhea-AI Filing Summary

Upwork CEO Hayden Brown reported multiple transactions on June 18, 2025, involving the company's common stock and restricted stock units (RSUs):

• Acquired 46,410 shares through the vesting of RSUs (17,733 + 28,677 shares)
• Sold 23,716 shares at an average price of $13.51 to cover tax withholding obligations
• Following these transactions, Brown directly owns 1,153,485 shares
• Maintains 625,228 unvested RSUs (195,066 + 430,162)

The RSUs vest quarterly over four-year periods starting June 18, 2024, and June 18, 2025, respectively. The share sale was mandatory for tax purposes and not a discretionary trade. Brown serves as both Director and President & CEO of Upwork.

Insider Trade Summary

Exercise and sale activity reported; no spread calculated

Exercise and Sale 5 txns

Insider Brown Hayden

Role President & CEO

Sold 23,716 shs ($320K)

Approx. gross sale proceeds $320K

Approx. exercise cost $0.00

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units	17,733	$0.00	$0.00
Exercise	Restricted Stock Units	28,677	$0.00	$0.00
Exercise	Common Stock	17,733	$0.00	$0.00
Exercise	Common Stock	28,677	$0.00	$0.00
Sale	Common Stock	23,716	$13.5054	$320K

Holdings After Transaction: Restricted Stock Units — 625,228 contracts (Direct); Common Stock — 1,153,485 shares (Direct)

Footnotes (5)

1. F1. Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
2. 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.
3. 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.
4. 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.
5. 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.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

How many UPWK shares did CEO Hayden Brown acquire through RSU vesting on June 18, 2025?

CEO Hayden Brown acquired a total of 46,410 shares through RSU vesting on June 18, 2025, consisting of 17,733 shares from one RSU grant and 28,677 shares from another RSU grant.

How many UPWK shares did Hayden Brown sell on June 18, 2025?

Hayden Brown sold 23,716 shares at a weighted average price of $13.5054 per share. This sale was specifically to cover tax withholding obligations related to the RSU vesting and was mandated by Upwork's equity incentive plan requirements.

What is the vesting schedule for UPWK CEO's recent RSU grants?

The RSUs vest in two separate schedules: one grant vests in equal quarterly installments over four years beginning June 18, 2024, and another grant vests in equal quarterly installments over four years beginning June 18, 2025. Both are subject to continued employment.

How many UPWK shares does CEO Hayden Brown own after the June 18, 2025 transactions?

Following the reported transactions, CEO Hayden Brown directly owns 1,153,485 shares of Upwork common stock. Additionally, she holds 195,066 unvested RSUs from one grant and 430,162 unvested RSUs from another grant.

What was the price range of UPWK shares sold in the tax-related sale?

The shares were sold in multiple transactions at prices ranging from $13.24 to $13.73 per share, with a weighted average price of $13.5054 per share.

AI-generated analysis. How Rhea-AI works. Not financial advice.

Form 4 Insider Transactions: What Each Field Means →

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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).

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)
06/18/2025

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	06/18/2025		M		17,733	A	(1)	1,148,524	D
Common Stock	06/18/2025		M		28,677	A	(1)	1,177,201	D
Common Stock	06/18/2025		S(2)		23,716	D	$13.5054(3)	1,153,485	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 Units	(1)	06/18/2025		M			17,733	(4)	(4)	Common Stock	17,733	$0.00	195,066	D
Restricted Stock Units	(1)	06/18/2025		M			28,677	(5)	(5)	Common Stock	28,677	$0.00	430,162	D

Explanation of Responses:

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

2. 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.

3. 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.

4. 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.

5. 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	06/23/2025
	** 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.