Upwork (NASDAQ: UPWK) COO sells shares to cover RSU tax bill

Rhea-AI Filing Summary

Upwork, Inc. GM & Chief Operating Officer Anthony Ray Kappus reported routine equity compensation activity involving RSUs and a related tax sale. On May 18, 2026, 5,114 shares of common stock were acquired upon the conversion of restricted stock units at a price of $0.00 per share. On the same date, 1,905 shares of common stock were sold at a weighted average price of $8.6634 per share, within a range of $8.57 to $8.73 per share, to cover tax withholding obligations under a mandatory “sell to cover” arrangement, which the footnotes state was not a discretionary trade. After these transactions, Kappus directly holds 3,209 shares of common stock and 76,719 restricted stock units that each represent a right to receive one share of common stock, vesting in equal quarterly installments over four years beginning on May 18, 2026, subject to continued employment.

Insights

Equity compensation analyst

COO’s Form 4 shows RSU vesting with a mandated tax sale, a routine non-discretionary event.

The filing shows Anthony Ray Kappus acquiring 5,114 common shares at $0.00 per share through the conversion of restricted stock units, while 1,905 shares were sold around $8.6634 to satisfy tax withholding. Footnotes clarify this “sell to cover” was required by Upwork’s equity plan, not an elective sale.

Following the transactions, he directly owns 3,209 common shares and 76,719 RSUs. The RSUs vest in equal quarterly installments over four years starting on May 18, 2026, contingent on continued employment. This pattern is typical for senior executive compensation and does not, by itself, signal a change in sentiment.

Insider Trade Summary

Net Seller: 1,905 shares ($16,504)

Net Sell 3 txns

Insider Kappus Anthony Ray

Role GM & Chief Operating Officer

Sold 1,905 shs ($17K)

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units	5,114	$0.00	--
Exercise	Common Stock	5,114	$0.00	--
Sale	Common Stock	1,905	$8.6634	$17K

Holdings After Transaction: Restricted Stock Units — 76,719 shares (Direct, null); Common Stock — 5,114 shares (Direct, null)

Footnotes (1)

1. 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 $8.57 to $8.73 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, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Key Figures

Shares sold for taxes: 1,905 shares Weighted average sale price: $8.6634 per share Shares acquired via RSU conversion: 5,114 shares +3 more

6 metrics

Shares sold for taxes 1,905 shares Common stock sold on May 18, 2026 to cover tax withholding

Weighted average sale price $8.6634 per share Sale price range $8.57–$8.73 on May 18, 2026

Shares acquired via RSU conversion 5,114 shares Common stock acquired at $0.00 per share on May 18, 2026

Common shares held after transactions 3,209 shares Direct holdings following May 18, 2026 transactions

RSUs held after transactions 76,719 RSUs Restricted stock units outstanding after May 18, 2026

RSU vesting schedule Four years, quarterly Equal quarterly installments beginning May 18, 2026

Key Terms

Restricted Stock Units, sell to cover, weighted average price, equity incentive plans, +1 more

5 terms

Restricted Stock Units financial

"security_title: "Restricted Stock Units" and footnote defining each RSU"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

sell to cover financial

"tax withholding obligations to be funded by a "sell to cover" transaction"

Sell to cover is when a person who receives company stock through options or awards sells just enough shares immediately to pay required taxes, exercise costs, or fees, keeping the rest. Think of it like cashing part of a bonus to cover the tax bill so you can keep the remainder. For investors, it can create predictable small selling pressure and slightly change the number of shares actually held by insiders without increasing long‑term dilution.

weighted average price financial

"The reported price in Column 4 is a weighted average price."

Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.

equity incentive plans financial

"mandated by the Issuer's election under its equity incentive plans"

Equity incentive plans are company programs that pay employees, executives, or directors with company stock, stock options, or share units instead of or in addition to cash, aiming to align their interests with shareholders—like giving team members a stake in the house they help build. For investors this matters because such plans can motivate better company performance but also dilute existing ownership and increase reported compensation costs, so they affect future earnings, voting power, and share value.

contingent right financial

"Each restricted stock unit ("RSU") represents a contingent right to receive one share"

Form 4 Insider Transactions: What Each Field Means →

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^*

Kappus Anthony Ray

(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 & Chief Operating Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/18/2026

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	05/18/2026		M		5,114	A	(1)	5,114	D
Common Stock	05/18/2026		S(2)		1,905	D	$8.6634(3)	3,209	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)	05/18/2026		M			5,114	(4)	(4)	Common Stock	5,114	$0.00	76,719	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 $8.57 to $8.73 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, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	05/20/2026
	** 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) COO Anthony Ray Kappus report?

Anthony Ray Kappus reported RSU vesting and a related tax sale. He acquired 5,114 shares of Upwork common stock via RSU conversion and sold 1,905 shares around a weighted average price of $8.6634 per share to cover tax withholding obligations.

Was the Upwork (UPWK) COO’s share sale a discretionary trade?

The sale was described as a mandatory tax “sell to cover.” Footnotes state 1,905 shares were sold to fund tax withholding obligations required by Upwork’s equity incentive plans, meaning the transaction did not represent a discretionary open-market decision by the executive.

How many Upwork (UPWK) shares and RSUs does the COO hold after these transactions?

After the transactions, the COO holds both stock and RSUs. He directly owns 3,209 shares of Upwork common stock and 76,719 restricted stock units, each RSU representing a contingent right to receive one share of common stock in the future.

At what prices were the Upwork (UPWK) COO’s shares sold to cover taxes?

The sale used a weighted average price of $8.6634 per share. Footnotes explain that the 1,905 shares were sold in multiple trades with prices ranging from $8.57 to $8.73 per share, inclusive, to satisfy tax withholding needs.

How do the Upwork (UPWK) COO’s RSUs vest after this Form 4 filing?

The RSUs vest gradually over four years. Footnotes state that the restricted stock units vest in equal quarterly installments over four years beginning on May 18, 2026, provided Anthony Ray Kappus remains employed by Upwork on each vesting date.

What does each restricted stock unit (RSU) represent for Upwork (UPWK) COO compensation?

Each RSU equals a right to one Upwork common share. The filing explains that every restricted stock unit represents a contingent right to receive one share of the company’s common stock, subject to vesting conditions tied primarily to continued employment.