[Form 4] UPWORK, INC Insider Trading Activity

Rhea-AI Filing Summary

Dave Bottoms, GM, Marketplace at Upwork, Inc. (UPWK), reported issuance and sales tied to restricted stock units (RSUs) and a Rule 10b5-1 plan. On 09/18/2025 and 09/19/2025 the reporting person had multiple non-derivative and derivative transactions: vesting RSUs were recorded (8,980; 6,024; 5,904 RSUs) that convert one-for-one into common shares when vested. To satisfy tax-withholding, 10,894 shares were sold on 09/18/2025 at a weighted average price of $19.1646 and 10,014 shares were sold on 09/19/2025 under a 10b5-1 plan at a weighted average price of $19.9588. Following these transactions the reporting person beneficially owned 345 shares (after the 09/19 sale). The RSUs vest quarterly over four years per the stated grant schedules.

Positive

• Clear disclosure of RSU vesting schedules and amounts (8,980; 6,024; 5,904 RSUs) with one-for-one conversion to common stock
• Sell-to-cover sale explicitly identified as required by the issuer's equity incentive plans (not a discretionary trade)
• 10b5-1 plan sale disclosed with adoption date (May 30, 2025) and weighted-average price ranges provided

Negative

• Material reduction in holdings: reporting person beneficial ownership decreased to 345 shares after reported sales
• Large share sales on 09/18/2025 and 09/19/2025 (10,894 and 10,014 shares) which may reduce insider stake materially

Insights

Financial Analyst

TL;DR: Insider sales were largely mechanical (tax withholding and a pre-existing 10b5-1 plan) and reduced beneficial ownership materially.

The filing shows vesting of multiple RSU grants that convert 1:1 to common shares and scheduled quarterly vesting over four-year periods. The reporting person sold 10,894 shares on 09/18/2025 to cover tax withholding and sold 10,014 shares on 09/19/2025 under a Rule 10b5-1 plan at weighted average prices of $19.1646 and $19.9588 respectively, leaving a beneficial ownership of 345 shares. These are routine equity-compensation and plan-driven transactions rather than discretionary open-market selling.

Corporate Governance Expert

TL;DR: Transactions conform to equity-plan mechanics and 10b5-1 procedures, with clear disclosure of sell-to-cover and plan-driven sales.

The Form 4 discloses required "sell-to-cover" withholding tied to vesting RSUs and sales under a 10b5-1 schedule adopted May 30, 2025. Footnotes detail weighted-average price ranges and the issuer's mandatory tax-withholding policy. The filing includes an attorney-in-fact signature, consistent with standard practice. Disclosure is specific and appears complete based on provided entries.

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^*

Bottoms Dave

(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)
	GM, Marketplace

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		8,980	A	(1)	9,325	D
Common Stock	09/18/2025		M		6,024	A	(1)	15,349	D
Common Stock	09/18/2025		M		5,904	A	(1)	21,253	D
Common Stock	09/18/2025		S(2)		10,894	D	$19.1646(3)	10,359	D
Common Stock	09/19/2025		S(4)		10,014	D	$19.9588(5)	345	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			8,980	(6)	(6)	Common Stock	8,980	$0.00	35,920	D
Restricted Stock Units	(1)	09/18/2025		M			6,024	(7)	(7)	Common Stock	6,024	$0.00	60,235	D
Restricted Stock Units	(1)	09/18/2025		M			5,904	(8)	(8)	Common Stock	5,904	$0.00	82,658	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. This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on May 30, 2025.

5. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $19.64 to $20.35 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 in equal quarterly installments over four years beginning on December 18, 2022, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

7. 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.

8. 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.
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 transactions did the Upwork (UPWK) insider report on Form 4?

Answer: The filing reports vesting of RSUs (8,980; 6,024; 5,904) and sales of 10,894 shares on 09/18/2025 and 10,014 shares on 09/19/2025.

Why were shares sold on 09/18/2025 according to the Form 4?

Answer: The 09/18/2025 sale of 10,894 shares was a mandated "sell-to-cover" to satisfy tax-withholding obligations tied to RSU vesting.

Were any sales executed under a 10b5-1 plan?

Answer: Yes. The 09/19/2025 sale of 10,014 shares was effected pursuant to a Rule 10b5-1 plan adopted May 30, 2025.

What prices were reported for the shares sold?

Answer: 09/18/2025 sales reported a weighted-average price of $19.1646 (range $18.89–$19.495). 09/19/2025 sales reported $19.9588 weighted-average (range $19.64–$20.35).

How many shares does the reporting person beneficially own after these transactions?

Answer: The Form 4 reports the reporting person beneficially owned 345 shares following the 09/19/2025 transactions.