Upwork (UPWK) COO exercises RSUs, sells 558 shares for taxes

Rhea-AI Filing Summary

Upwork, Inc.’s GM & Chief Operating Officer Anthony Ray Kappus reported RSU vesting on July 18, 2026, converting 1,412 RSUs into the same number of common shares at no cost. To satisfy tax withholding from this vesting, 558 shares were automatically sold in a required “sell to cover” transaction at a weighted average price of $9.0554 per share. After the transaction, he reported holding 21,191 RSUs that vest in equal quarterly installments over four years beginning July 18, 2026, subject to continued employment.

Insider Trade Summary

Exercise and sale activity reported; no spread calculated

Exercise and Sale 3 txns

Insider Kappus Anthony Ray

Role GM & Chief Operating Officer

Sold 558 shs ($5K)

Approx. gross sale proceeds $5K

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units F1, F4	1,412	$0.00	$0.00
Exercise	Common Stock F1	1,412	--	--
Sale	Common Stock F2, F3	558	$9.0554	$5K

Holdings After Transaction: Restricted Stock Units — 21,191 shares (Direct); Common Stock — 4,063 shares (Direct)

Footnotes (4)

1. F1. Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
2. F2. 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. F3. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $9.01 to $9.12 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. F4. The RSUs vest in equal quarterly installments over four years beginning on July 18, 2026, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Key Figures

Shares acquired via RSU conversion: 1,412 shares Shares sold to cover taxes: 558 shares Weighted average sale price: $9.0554 per share +3 more

6 metrics

Shares acquired via RSU conversion 1,412 shares Common stock received from RSU vesting on July 18, 2026

Shares sold to cover taxes 558 shares Automatic sell-to-cover transaction tied to RSU vesting

Weighted average sale price $9.0554 per share Weighted average for 558 shares sold

Sale price range $9.01–$9.12 per share Range of prices for multiple sale transactions

RSUs exercised 1,412 RSUs Restricted Stock Units converted into common stock

RSUs remaining after transaction 21,191 RSUs RSUs vesting quarterly over four years from July 18, 2026

Key Terms

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

4 terms

Restricted Stock Units financial

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

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

"require the satisfaction of 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.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Form 4 Insider Transactions: What Each Field Means →

Available on EDGAR 07/21/2026 - 04:41 PM Accepted by SEC EDGAR 07/21/2026 - 04:40 PM Learn about SEC filing dates

FAQ

What transactions did UPWK executive Anthony Ray Kappus report on July 18, 2026?

He reported RSU vesting into 1,412 Upwork (UPWK) shares and an automatic sale of 558 shares. The sale was solely to cover tax withholding from the RSU vesting under the company’s equity incentive plans, not a discretionary trade.

How many Upwork (UPWK) shares did Kappus acquire through RSU vesting?

Kappus acquired 1,412 shares of Upwork common stock when an equal number of RSUs vested. Each restricted stock unit represents a contingent right to receive one share of common stock upon vesting, subject to continued employment conditions.

Why were 558 UPWK shares sold, and at what price were they sold?

The 558 shares were sold to cover tax withholding obligations from the RSU vesting. They were sold at a weighted average price of $9.0554 per share, in multiple transactions ranging between $9.01 and $9.12 per share.

How many Upwork (UPWK) RSUs does Anthony Ray Kappus hold after these transactions?

After the reported RSU vesting, Kappus reported holding 21,191 RSUs. These restricted stock units are scheduled to vest in equal quarterly installments over four years beginning on July 18, 2026, subject to his continued employment with Upwork.

Were the UPWK share sales by Kappus discretionary or mandated?

The 558-share sale was mandated by Upwork’s equity incentive plans as a “sell to cover” tax transaction. It was executed solely to fund required tax withholding from the RSU vesting and is explicitly described as not a discretionary trade by Kappus.

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)
07/18/2026

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	07/18/2026		M		1,412	A	(1)	4,621	D
Common Stock	07/18/2026		S(2)		558	D	$9.0554(3)	4,063	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)	07/18/2026		M			1,412	(4)	(4)	Common Stock	1,412	$0.00	21,191	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 $9.01 to $9.12 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 July 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	07/21/2026
	** 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)