[Form 4] Upwork Inc. Insider Trading Activity

Rhea-AI Filing Summary

Dave Bottoms, listed as an officer (GM, Marketplace) of Upwork, Inc. (UPWK), reported a sale of 1,690 shares of Upwork common stock on 08/29/2025 at a price of $14.95 per share. The filing shows 345 shares remained beneficially owned by the reporting person after the transaction. The sale was executed under a Rule 10b5-1 trading plan adopted by the reporting person on May 30, 2025, and the Form 4 was signed by an attorney-in-fact, Jacob McQuown, on 09/03/2025. No derivatives or additional transactions are reported in this filing.

Positive

• Transaction disclosed promptly on Form 4 with specific share count and price
• Sale executed under a Rule 10b5-1 plan, indicating a pre-established trading arrangement and procedural compliance

Negative

• Officer reduced holdings to 345 shares following the sale, indicating a small remaining ownership stake

Insights

Securities/Equity Analyst

TL;DR: Officer sold a small block of shares under a pre-established 10b5-1 plan; remaining stake is minimal.

The reported sale of 1,690 shares at $14.95 is a routine, disclosed disposition by an officer using a Rule 10b5-1 plan adopted May 30, 2025. The filing indicates the officer retains 345 shares after the sale, which represents a small residual holding and limits any signal of continued large insider ownership. Because this is a single non-derivative sale with no additional context in the Form 4, the transaction appears procedural and compliant with insider trading plan requirements.

Corporate Governance Expert

TL;DR: Sale follows a documented 10b5-1 plan, demonstrating adherence to insider-trading governance procedures.

The Form 4 clearly states the sale was effected pursuant to a Rule 10b5-1 plan adopted on May 30, 2025, which provides an affirmative defense framework for scheduled insider transactions. The attestation by an attorney-in-fact and the explicit plan reference support procedural compliance. The filing does not disclose any other executive changes, option exercises, or derivative activity.

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).

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)
08/29/2025

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	08/29/2025		S(1)		1,690	D	$14.95	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

Explanation of Responses:

1. This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on May 30, 2025.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	09/03/2025
	** 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 insider transaction did UPWK officer Dave Bottoms report?

The Form 4 reports a sale of 1,690 shares of Upwork common stock executed on 08/29/2025.

At what price were the UPWK shares sold in the Form 4?

The reported sale price was $14.95 per share.

Was the Upwork insider sale part of a 10b5-1 plan (UPWK)?

Yes. The filing states the transaction was effected pursuant to a Rule 10b5-1 plan adopted by the reporting person on May 30, 2025.

How many Upwork shares does the reporting person own after the transaction?

The Form 4 shows the reporting person beneficially owned 345 shares following the reported sale.

Who signed the Form 4 for the UPWK reporting person?

The Form 4 is signed by Jacob McQuown, Attorney-in-Fact, dated 09/03/2025.