Upwork (UPWK) GM Dave Bottoms sells 18,575 shares after RSU vesting

Rhea-AI Filing Summary

Upwork, Inc. GM, Marketplace Dave Bottoms reported a mix of RSU vesting and share sales. On March 18, 2026, he converted a total of 20,908 Restricted Stock Units into an equal number of common shares at a conversion price of $0.00 per share, reflecting routine equity compensation vesting.

On the same day, he sold 11,575 common shares at a weighted average price of $12.3118 per share, followed by an additional sale of 7,000 shares on March 19, 2026 at a weighted average price of $11.4926 per share. Footnotes state that part of the shares sold were required to cover tax withholding obligations through a “sell to cover” transaction under Upwork’s equity incentive plans, meaning those sales were not discretionary trades.

Another footnote explains that the transactions were effected pursuant to a Rule 10b5-1 trading plan adopted on May 30, 2025, indicating the sales were pre-planned. After these transactions, Bottoms directly holds 2,678 shares of Upwork common stock, alongside ongoing RSU awards that vest in equal quarterly installments over four-year periods beginning on December 18, 2022, June 18, 2024, and June 18, 2025, subject to continued employment.

Insights

Equity compensation and insider-trading analyst

Routine RSU vesting with pre-planned and tax-driven sales; limited signal.

Dave Bottoms, GM of Marketplace at Upwork, reported conversion of 20,908 RSUs into common shares and total open-market sale activity of 18,575 shares. The data and footnotes show a standard equity compensation cycle rather than an abrupt portfolio shift.

One block of shares was sold to satisfy tax withholding obligations via a mandated “sell to cover” mechanism under the company’s equity plans, which is mechanical and not a discretionary decision. A separate footnote states the transactions were executed under a Rule 10b5-1 trading plan adopted on May 30, 2025, suggesting the timing was pre-scheduled.

Following these transactions, Bottoms holds 2,678 shares directly, and the RSU tables indicate continued unvested awards with quarterly vesting over four-year terms starting on December 18, 2022, June 18, 2024, and June 18, 2025. Given the pre-planned and tax-driven nature of much of the activity, this filing appears routine and is unlikely to materially alter an informed view of Upwork’s equity story.

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 CALIFORNIA 94301

(City) (State) (Zip)

UNITED STATES

(Country)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
03/18/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	03/18/2026		M		8,980	A	(1)	9,325	D
Common Stock	03/18/2026		M		6,024	A	(1)	15,349	D
Common Stock	03/18/2026		M		5,904	A	(1)	21,253	D
Common Stock	03/18/2026		S(2)		11,575	D	$12.3118(3)	9,678	D
Common Stock	03/19/2026		S(4)		7,000	D	$11.4926(5)	2,678	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)	03/18/2026		M			8,980	(6)	(6)	Common Stock	8,980	$0.00	17,960	D
Restricted Stock Units	(1)	03/18/2026		M			6,024	(7)	(7)	Common Stock	6,024	$0.00	48,188	D
Restricted Stock Units	(1)	03/18/2026		M			5,904	(8)	(8)	Common Stock	5,904	$0.00	70,850	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 $12.13 to $12.52 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 $11.33 to $11.72 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	03/20/2026
	** 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.
* Form 4: SEC 1474 (03-26)

FAQ

What insider transactions did Upwork (UPWK) executive Dave Bottoms report?

Dave Bottoms reported RSU vesting into 20,908 common shares and total sales of 18,575 shares. The filing shows routine equity compensation events combined with pre-planned and tax-related share sales rather than purely discretionary trading activity.

How many Upwork (UPWK) shares did Dave Bottoms sell and at what prices?

He sold 11,575 Upwork common shares at a weighted average price of $12.3118 and 7,000 shares at $11.4926. Footnotes note both transactions occurred through multiple trades within stated price ranges on March 18 and March 19, 2026.

Were Dave Bottoms’ Upwork (UPWK) share sales discretionary or pre-planned?

The filing states the transactions were effected under a Rule 10b5-1 plan adopted on May 30, 2025. This indicates the sales were pre-planned rather than opportunistic, reducing the informational value of their specific timing for investors evaluating insider sentiment.

What part of Dave Bottoms’ Upwork (UPWK) share sales covered tax withholding?

A footnote explains that a portion of the shares sold represented those required to cover tax withholding obligations tied to RSU vesting. The company’s equity plan mandates a “sell to cover” approach, so these shares were sold mechanically, not through a discretionary trading decision by Bottoms.

How many Upwork (UPWK) shares does Dave Bottoms hold after these transactions?

After completing the RSU conversions and share sales, Bottoms directly holds 2,678 shares of Upwork common stock. In addition, the RSU table shows unvested awards scheduled to vest quarterly over four-year periods, contingent on his continued employment with the company.

How do Dave Bottoms’ Upwork (UPWK) RSUs vest over time?

Footnotes state his RSUs vest in equal quarterly installments over four years starting on December 18, 2022, June 18, 2024, and June 18, 2025. Each vesting date requires his continued employment, reflecting standard time-based equity compensation structures for senior executives.