[Form 4] Upwork Inc. Insider Trading Activity

Rhea-AI Filing Summary

Dave Bottoms, an officer (GM, Marketplace) of Upwork, Inc. (UPWK), reported equity activity on 08/18/2025. 3,750 restricted stock units (RSUs) vested and were recorded as acquired, representing the contingent right to receive one share each. Concurrently, 2,060 shares were sold to satisfy tax-withholding obligations under the company’s mandatory "sell-to-cover" program at a weighted-average price of $13.837 per share (sales ranged $13.74–$13.987). After these transactions, the filing shows the reporting person directly beneficially owned 4,095 shares of common stock and held 22,500 RSUs total. The sale to cover was not a discretionary trade but a plan-mandated withholding method.

Positive

• 3,750 RSUs vested, increasing the reporting person's immediate equity alignment with shareholders
• Filing discloses sell-to-cover was plan-mandated (not a discretionary sale), improving transparency

Negative

• 2,060 shares sold to cover taxes, modestly reducing the reporting person's direct share count

Insights

Financial Analyst

TL;DR Routine RSU vesting with mandated sell-to-cover taxes; immaterial to Upwork’s capital structure.

The filing documents the vesting of 3,750 RSUs and an accompanying sell-to-cover of 2,060 shares at a weighted-average price of $13.837. This is a standard compensation settlement event rather than an opportunistic insider sale. The net change in direct common shares is modest (report shows 4,095 shares beneficially owned post-transaction). There is no indication of open-market trading beyond the tax withholding disposition and no derivative exercises beyond RSU vesting. For investors, this transaction is administrative and does not signal company-level operational changes.

Corporate Governance Expert

TL;DR Compensation-driven disclosure aligns with governance expectations; sell-to-cover is plan-compliant.

The Form 4 clarifies that the share disposals were mandated by the issuer’s equity plan to satisfy tax withholding upon RSU vesting, which is consistent with prudent governance and typical equity compensation practices. The reporting person remains an officer and retains a larger position in unvested RSUs (22,500), indicating continued alignment with shareholder interests. The filing is transparent about price range and provides an undertaking to disclose per-price breakouts if requested.

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

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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).

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)
08/18/2025

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	08/18/2025		M		3,750	A	(1)	4,095	D
Common Stock	08/18/2025		S(2)		2,060	D	$13.837(3)	2,035	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)	08/18/2025		M			3,750	(4)	(4)	Common Stock	3,750	$0.00	22,500	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 $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.

4. The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023, subject to the continuing employment of the Reporting Person on each vesting date.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	08/20/2025
	** 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 UPWK officer Dave Bottoms report on Form 4?

The report shows 3,750 RSUs vested on 08/18/2025 and a concurrent sell-to-cover of 2,060 shares to satisfy tax withholding.

At what price were the shares sold in the sell-to-cover transaction?

The shares were sold at a weighted-average price of $13.837 per share, with individual sale prices ranging from $13.74 to $13.987.

How many shares and RSUs does the reporting person hold after the transactions?

After the reported transactions the filing shows 4,095 shares beneficially owned directly and 22,500 RSUs beneficially owned following the reported transactions.

Was the sale a discretionary insider trade?

No. The sale was a mandatory sell-to-cover required by the issuer’s equity incentive plan to satisfy tax withholding obligations.

Does the Form 4 indicate any option exercises or other derivative activity?

No option exercises are reported; the only derivative-related item is the vesting of 3,750 RSUs that convert into common stock.