[Form 4] Upwork Inc. Insider Trading Activity

Rhea-AI Filing Summary

Marie Olivier, Chief Accounting Officer of Upwork, Inc. (UPWK), reported several transactions in August 2025. On 08/14/2025 she sold 1,294 shares under a Rule 10b5-1 plan at a weighted average price of $14 per share. On 08/18/2025 she had restricted stock units vest and be settled: 1,427 RSUs and 1,200 RSUs (each RSU converts to one share). To satisfy tax withholding upon vesting, she had 941 shares sold in a sell-to-cover at a weighted average price of $13.8367 per share. Following the reported transactions, she beneficially owned 2,434 shares (after the 08/14 sale) and later 3,375 and 2,434 shares as shown in the filing; Table II shows 2,854 and 2,400 underlying shares resulting from the settled RSUs. The filing states the 08/14 sale was pursuant to a 10b5-1 plan adopted May 15, 2025, and that sell-to-cover was required by the issuer's equity plan.

Insights

Financial Analyst

TL;DR: Routine insider activity tied to RSU vesting and tax-withholding sales with limited material market impact.

The transactions are primarily non-discretionary: two RSU vesting events converted to common shares and a sell-to-cover sale satisfied tax withholding obligations; an earlier sale was executed under a 10b5-1 plan. Quantities are modest relative to typical market floats for a public company: sales of 1,294 and 941 shares and RSU settlements of 1,427 and 1,200 RSUs. The filing discloses weighted average sale prices and the plan adoption date, all of which are transparent and consistent with routine executive compensation administration.

Corporate Governance Expert

TL;DR: Disclosure appears complete and follows standard governance practices for equity awards and 10b5-1 trading plans.

The report identifies the reporting person, role (Chief Accounting Officer), relationship to the issuer, and cites the 10b5-1 plan adoption date (May 15, 2025). It documents RSU vesting schedules and the issuer-mandated sell-to-cover for tax withholding. Signatures and explanatory footnotes are included, indicating adherence to Form 4 requirements; no governance irregularities or omissions are evident from the provided content.

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

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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).

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^*

Marie Olivier

(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 Accounting Officer

3. Date of Earliest Transaction (Month/Day/Year)
08/14/2025

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	08/14/2025		S(1)		1,294	D	$14	748	D
Common Stock	08/18/2025		M		1,427	A	(2)	2,175	D
Common Stock	08/18/2025		M		1,200	A	(2)	3,375	D
Common Stock	08/18/2025		S(3)		941	D	$13.8367(4)	2,434	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	(2)	08/18/2025		M			1,427	(5)	(5)	Common Stock	1,427	$0.00	2,854	D
Restricted Stock Units	(2)	08/18/2025		M			1,200	(6)	(6)	Common Stock	1,200	$0.00	2,400	D

Explanation of Responses:

1. This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on May 15, 2025.

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 $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.

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

6. The RSUs vest in equal quarterly installments over three 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	08/18/2025
	** 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 insider transactions did Marie Olivier (UPWK) report in August 2025?

She sold 1,294 shares on 08/14/2025 under a 10b5-1 plan and had RSUs vest on 08/18/2025 totaling 2,627 RSUs (1,427 and 1,200).

Why were shares sold on 08/18/2025 in the Form 4 for UPWK?

941 shares were sold as a sell-to-cover to satisfy tax withholding obligations required by the issuer's equity incentive plans.

What price information is provided in the Form 4 for the sales?

The 08/14 sale reports a weighted average price of $14.00 per share; the 08/18 sell-to-cover reports a weighted average of $13.8367 per share, with trades ranging $13.74–$13.987.

Did the filing reference a trading plan for the sales?

Yes. The 08/14 transaction was effected pursuant to a Rule 10b5-1 plan adopted May 15, 2025.

How many shares did Marie Olivier beneficially own after the reported transactions?

The filing lists beneficial ownership amounts after transactions, including figures such as 2,434 and 3,375 shares as shown in the Tables.