Were any of the Upwork (UPWK) share sales related to tax withholding?

Yes. A portion of the reported sales represents shares sold to cover tax withholding obligations arising from RSU vesting, under the issuer’s equity incentive plan election to use mandatory “sell to cover” transactions.

Upwork insider files Form 4 detailing RSU vesting and share sales

Q: What insider activity did Upwork (UPWK) report in this Form 4?

The GM, Marketplace of Upwork Inc. (UPWK) reported sales of common stock and the vesting and settlement of 3,750 RSUs into shares between November 17 and 19, 2025 , along with updated beneficial ownership.

Q: How many Upwork shares did the insider sell and at what prices?

The reporting person sold 561 shares at $16.45 on November 17, 2025 , 955 shares at a weighted average of $16.1426 and 1,047 shares at a weighted average of $17.2393 on November 18 , and 1,748 shares at a weighted average of $18.1293 on November 19 .

Q: What RSU activity did the Upwork (UPWK) executive report?

On November 18, 2025 , 3,750 restricted stock units (RSUs) were converted into an equal number of Upwork common shares. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023 , subject to continued employment.

Q: What is the insiders remaining Upwork (UPWK) ownership after these transactions?

After the reported transactions, the insider directly held 345 shares of Upwork common stock and 18,750 RSUs , each RSU representing a contingent right to receive one share of common stock.

Q: Was a Rule 10b5-1 trading plan used for the Upwork (UPWK) stock sales?

Yes. One of the transactions was effected under a Rule 10b5-1 trading plan adopted by the reporting person on May 30, 2025 , which is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).

Filing Impact

(Neutral)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Upwork Inc. (UPWK) executive GM, Marketplace reported several equity transactions. On November 17, 2025, the reporting person sold 561 shares of common stock at $16.45 per share under a Rule 10b5-1 trading plan. On November 18, 2025, 3,750 restricted stock units (RSUs) were converted into common shares, and the person then sold 955 shares at a weighted average price of $16.1426 and 1,047 shares at a weighted average price of $17.2393. On November 19, 2025, an additional 1,748 shares were sold at a weighted average price of $18.1293.

Some of the sales were required to cover tax withholding obligations tied to RSU vesting, described as “sell to cover” transactions rather than discretionary trades. Following these transactions, the reporting person directly owned 345 shares of Upwork common stock and 18,750 RSUs, each RSU representing one share that vests quarterly over four years beginning on May 18, 2023.

Insider Trade Summary

Net Seller: 4,311 shares ($74,384)

Net Sell 6 txns

Insider Bottoms Dave

Role GM, Marketplace

Sold 4,311 shs ($74K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,748	$18.1293	$32K
Exercise	Restricted Stock Units	3,750	$0.00	--
Exercise	Common Stock	3,750	$0.00	--
Sale	Common Stock	955	$16.1426	$15K
Sale	Common Stock	1,047	$17.2393	$18K
Sale	Common Stock	561	$16.45	$9K

Holdings After Transaction: Common Stock — 345 shares (Direct); Restricted Stock Units — 18,750 shares (Direct)

Footnotes (1)

This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on May 30, 2025. Reflects 561 shares acquired under the Issuer's employee stock purchase plan on November 14, 2025. Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock. 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. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.66 to $16.65 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. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $16.67 to $17.4932 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. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $17.80 to $18.36 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. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Form 4 Insider Transactions: What Each Field Means →

11/19/2025 - 07:18 PM

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).

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

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)
11/17/2025

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	11/17/2025		S⁽¹⁾		561	D	$16.45	345⁽²⁾	D
Common Stock	11/18/2025		M		3,750	A	⁽³⁾	4,095	D
Common Stock	11/18/2025		S⁽⁴⁾		955	D	$16.1426⁽⁵⁾	3,140	D
Common Stock	11/18/2025		S⁽⁴⁾		1,047	D	$17.2393⁽⁶⁾	2,093	D
Common Stock	11/19/2025		S⁽¹⁾		1,748	D	$18.1293⁽⁷⁾	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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Restricted Stock Units	⁽³⁾	11/18/2025		M			3,750	⁽⁸⁾	⁽⁸⁾	Common Stock	3,750	$0.00	18,750	D

Explanation of Responses:

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

2. Reflects 561 shares acquired under the Issuer's employee stock purchase plan on November 14, 2025.

3. Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.

4. 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.

5. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.66 to $16.65 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $16.67 to $17.4932 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.

7. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $17.80 to $18.36 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.

8. The RSUs vest in equal quarterly installments over four 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	11/19/2025
	** 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.

Source: View Original Filing on SEC EDGAR

FAQ

What insider activity did Upwork (UPWK) report in this Form 4?

The GM, Marketplace of Upwork Inc. (UPWK) reported sales of common stock and the vesting and settlement of 3,750 RSUs into shares between November 17 and 19, 2025, along with updated beneficial ownership.

How many Upwork shares did the insider sell and at what prices?

The reporting person sold 561 shares at $16.45 on November 17, 2025, 955 shares at a weighted average of $16.1426 and 1,047 shares at a weighted average of $17.2393 on November 18, and 1,748 shares at a weighted average of $18.1293 on November 19.

What RSU activity did the Upwork (UPWK) executive report?

On November 18, 2025, 3,750 restricted stock units (RSUs) were converted into an equal number of Upwork common shares. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023, subject to continued employment.

What is the insiders remaining Upwork (UPWK) ownership after these transactions?

After the reported transactions, the insider directly held 345 shares of Upwork common stock and 18,750 RSUs, each RSU representing a contingent right to receive one share of common stock.

Was a Rule 10b5-1 trading plan used for the Upwork (UPWK) stock sales?

Yes. One of the transactions was effected under a Rule 10b5-1 trading plan adopted by the reporting person on May 30, 2025, which is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c).