Upwork COO Kappus sells 559 shares to cover taxes

Q: How many UPWK shares did Anthony Ray Kappus sell, and at what price?

Anthony Ray Kappus sold 559 common shares on October 19, 2026, at a weighted average price of $8.4293 per share; the shares were sold in transactions ranging from $8.36 to $8.4950 per share. The sale was mandated to cover tax withholding and was not discretionary. No Rule 10b5-1 plan is reported.

Upwork’s COO’s 559-share sale was required to fund tax withholding on vested RSUs, rather than a discretionary trade.

Filing Impact

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Filing Sentiment

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Form Type

Rhea-AI Filing Summary

Upwork, Inc. GM & Chief Operating Officer Anthony Ray Kappus converted 1,413 restricted stock units into 1,413 common shares on October 18, 2026; his reported remaining RSU position was 19,778. On October 19, he sold 559 common shares at a weighted average of $8.4293 per share, in transactions ranging from $8.36 to $8.4950, to cover tax withholding. Upwork’s equity-plan election mandated the sell-to-cover transaction, which was not discretionary; no Rule 10b5-1 plan is reported.

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 559 shs ($5K)

Approx. gross sale proceeds $5K

Type	Security	Shares	Price	Value
Sale	Common Stock ^{F2, F3}	559	$8.4293	$5K
Exercise	Restricted Stock Units ^{F1, F4}	1,413	$0.00	$0.00
Exercise	Common Stock ^F1	1,413	--	--

Holdings After Transaction: Restricted Stock Units — 19,778 contracts (Direct); Common Stock — 77,196 shares (Direct)

Footnotes (4)

F1. Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
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.
F3. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $8.36 to $8.4950 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.
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

Common shares sold: 559 shares Weighted average sale price: $8.4293 per share Sale price range: $8.36 to $8.4950 per share +3 more

6 metrics

Common shares sold 559 shares October 19, 2026

Weighted average sale price $8.4293 per share Sale on October 19, 2026

Sale price range $8.36 to $8.4950 per share Multiple transactions

Restricted stock units converted 1,413 RSUs October 18, 2026

Common shares acquired upon conversion 1,413 shares October 18, 2026

RSUs following transaction 19,778 RSUs Reported after the October 18, 2026 transaction

Key Terms

restricted stock unit, sell to cover, weighted average price

3 terms

restricted stock unit financial

"Each restricted stock unit ("RSU") represents a contingent right"

A restricted stock unit is a promise from a company to give an employee shares of stock after certain conditions are met, like staying with the company for a set amount of time. It’s like earning a bonus that turns into company stock once you’ve proven your commitment, making it a way to motivate and reward employees.

sell to cover financial

"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.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

How many UPWK shares did Anthony Ray Kappus sell, and at what price?

Anthony Ray Kappus sold 559 common shares on October 19, 2026, at a weighted average price of $8.4293 per share; the shares were sold in transactions ranging from $8.36 to $8.4950 per share. The sale was mandated to cover tax withholding and was not discretionary. No Rule 10b5-1 plan is reported.

What were the vesting terms for Anthony Ray Kappus’s UPWK RSUs?

The RSUs vest in equal quarterly installments over four years beginning July 18, 2026, subject to his continued employment with Upwork on each vesting date.

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

Form 4 Insider Transactions: What Each Field Means →

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Available on EDGAR 10/20/2026 - 04:34 PM EDT Accepted by SEC EDGAR 10/20/2026 - 04:34 PM EDT

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)
10/18/2026

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)
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	10/18/2026		M		1,413	A	⁽¹⁾	77,755	D
Common Stock	10/19/2026		S⁽²⁾		559	D	$8.4293⁽³⁾	77,196	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	⁽¹⁾	10/18/2026		M			1,413	⁽⁴⁾	⁽⁴⁾	Common Stock	1,413	$0.00	19,778	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 $8.36 to $8.4950 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	10/20/2026
	** 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)

Source: View Original Filing on SEC EDGAR