[Form 4] Upwork Inc. Insider Trading Activity

Rhea-AI Filing Summary

Erica Gessert, Chief Financial Officer of Upwork, Inc. (UPWK) reported equity activity related to restricted stock units and a sell-to-cover tax-withholding transaction. On 08/18/2025, 37,500 RSUs vested, converting to 37,500 shares of common stock that were recorded as acquired. To satisfy tax withholding required by the company's equity plan, 19,036 shares were sold in multiple transactions at a weighted average price of $13.8352 per share (prices ranged $13.74–$13.987). After these transactions the reporting person held 209,202 shares of common stock and beneficially owned 262,500 shares underlying RSUs.

The filing notes the sell-to-cover was mandated by the issuer's election under its equity incentive plans and does not reflect a discretionary sale by the reporting person.

Insights

Financial Analyst

TL;DR: Routine executive equity vesting with mandated sell-to-cover; no material change to ownership stake beyond expected vesting mechanics.

The filing documents a standard vesting event of 37,500 RSUs and a concurrent sell-to-cover of 19,036 shares to satisfy tax obligations at a weighted average price of $13.8352. This is an administrative liquidity action driven by plan terms, not an opportunistic open-market divestiture. The net increase in common shares held (post-transaction 209,202) and total underlying RSU exposure (262,500) maintain executive alignment with shareholder interests. There is no indication of additional strategic or liquidity-driven dispositions.

Corporate Governance Expert

TL;DR: Transaction reflects standard equity-compensation governance and plan-enforced tax withholding; demonstrates plan mechanics working as intended.

The report explicitly states the sale was a "sell-to-cover" required by the issuer's equity incentive plan, which is a common governance practice to satisfy withholding without requiring cash payments by the executive. The disclosure is clear on number of RSUs vested, number of shares sold for withholding, and the price range, indicating appropriate SEC Section 16 reporting and transparency. No governance issues or discretionary insider selling are evidenced here.

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

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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^*

Gessert Erica

(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)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Financial Officer

3. Date of Earliest Transaction (Month/Day/Year)
08/18/2025

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	08/18/2025		M		37,500	A	(1)	228,238	D
Common Stock	08/18/2025		S(2)		19,036	D	$13.8352(3)	209,202	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)	08/18/2025		M			37,500	(4)	(4)	Common Stock	37,500	$0.00	262,500	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 $13.74 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.

4. 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.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	08/20/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
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