[Form 4] UPWORK, INC Insider Trading Activity

Rhea-AI Filing Summary

Erica Gessert, Chief Financial Officer of Upwork, Inc. (UPWK), reported multiple equity transactions on 09/18/2025. The filing shows acquisition of 8,433 and 9,700 restricted stock units (RSUs) that vest quarterly over four years, increasing RSU-based claims on common stock. Concurrently, 8,730 shares were sold as a mandatory "sell-to-cover" to satisfy tax-withholding obligations at a weighted-average price of $19.1641 per share. Following these events, the reporting person beneficially owned 218,605, 227,335, and other figures shown per transaction line, and held 84,329 and 135,796 shares attributable to vested RSUs in Table II. The sale was described as required by the company’s equity plan and not a discretionary trade.

Positive

• Acquisition of 18,133 RSUs (8,433 and 9,700) increases the reporting person’s long-term equity alignment with shareholders
• RSUs vest quarterly over four years, which supports executive retention and alignment with long-term performance

Negative

• Sale of 8,730 shares at a weighted-average price of $19.1641, though disclosed as a mandatory sell-to-cover rather than discretionary selling

Insights

Corporate Governance Expert

TL;DR: Routine, plan-driven equity vesting and mandatory sell-to-cover; governance controls appear in effect.

The Form 4 documents scheduled RSU vesting and an associated sell-to-cover to meet tax obligations, a common practice under equity compensation plans. The reporting person, the CFO, recorded two RSU accruals (8,433 and 9,700 RSUs) that vest quarterly over four years, which aligns compensation with continued service. The sale of 8,730 shares was explicitly mandated by the issuer to satisfy tax withholding and is described as non-discretionary. From a governance perspective, disclosures are complete and transparent regarding price range and the nature of the transactions.

Securities Analyst

TL;DR: Insider increased long-term equity exposure via RSUs while executing a routine sell-to-cover; no obvious signal of company-specific stress.

The transactions show net addition of RSU-based equity claims (total RSUs acquired 18,133) while a mandated sale reduced share count by 8,730 at a weighted-average price of $19.1641. The RSU vesting schedules (starting June 2024 and June 2025) indicate multi-year retention incentives. Because the sale was a plan-mandated tax withholding event, it should not be interpreted as a voluntary disposition driven by firm outlook. Overall, the filing is neutral for near-term valuation impact but confirms ongoing executive equity alignment with shareholder value over time.

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)
09/18/2025

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	09/18/2025		M		8,433	A	(1)	217,635	D
Common Stock	09/18/2025		M		9,700	A	(1)	227,335	D
Common Stock	09/18/2025		S(2)		8,730	D	$19.1641(3)	218,605	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)	09/18/2025		M			8,433	(4)	(4)	Common Stock	8,433	$0.00	84,329	D
Restricted Stock Units	(1)	09/18/2025		M			9,700	(5)	(5)	Common Stock	9,700	$0.00	135,796	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 $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.

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	09/22/2025
	** 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.
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FAQ

What transactions did UPWK insider Erica Gessert report on 09/18/2025?

The filing reports acquisition of 8,433 and 9,700 RSUs and a sell-to-cover sale of 8,730 shares at a weighted-average price of $19.1641.

Were the share sales by the UPWK CFO discretionary trades?

No; the filing states the sale was mandated by the issuer’s equity plan as a sell-to-cover to satisfy tax-withholding obligations.

How do the newly acquired RSUs vest?

One RSU grant vests in equal quarterly installments over four years beginning June 18, 2024; the other vests similarly beginning June 18, 2025.

How many RSUs were acquired in total in this Form 4?

A total of 18,133 RSUs were acquired (8,433 + 9,700) on 09/18/2025.

What price range were the sold shares executed at?

The sale transactions occurred at prices ranging from $18.89 to $19.495 per share, with a reported weighted-average of $19.1641.