Upwork COO sells 45,732 shares in tax sale

Upwork’s GM & COO had RSUs vest into shares, with part of the stock sold automatically to cover taxes under a mandated sell-to-cover arrangement.

Rhea-AI Filing Summary

UPWORK, INC (UPWK) reported that GM & Chief Operating Officer Anthony Ray Kappus had restricted stock units vest and convert into common stock on September 18, 2026. 114,860 RSUs converted into the same number of common shares, and a portion of those shares was sold to cover tax withholding obligations under the company’s mandated “sell to cover” policy, rather than as a discretionary trade. After this vesting event, Kappus held 344,582 RSUs directly.

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 45,732 shs ($386K)

Approx. gross sale proceeds $386K

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units F1, F4	114,860	$0.00	$0.00
Exercise	Common Stock F1	114,860	--	--
Sale	Common Stock F2, F3	45,732	$8.4508	$386K

Holdings After Transaction: Restricted Stock Units — 344,582 contracts (Direct); Common Stock — 76,342 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 $8.315 to $8.52 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. F4. The RSUs vest 25% on September 18, 2026, and then 1/16th of the total number of shares on each quarterly anniversary thereafter, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Key Figures

RSUs converted: 114,860 units Common shares acquired: 114,860 shares Shares sold: 45,732 shares +3 more

6 metrics

RSUs converted 114,860 units Restricted stock units vesting and converting into common stock on September 18, 2026

Common shares acquired 114,860 shares Shares received upon RSU conversion on September 18, 2026

Shares sold 45,732 shares Automatic sale to cover tax withholding obligations on September 18, 2026

Weighted average sale price $8.4508 per share Shares sold in multiple transactions between $8.315 and $8.52 per share

Remaining RSUs held 344,582 units RSUs directly held by Anthony Ray Kappus after the reported vesting event

RSU vesting schedule 25% on September 18, 2026, then 1/16 quarterly Vesting continues quarterly, subject to continued employment on each vesting date

Key Terms

Restricted Stock Units, sell to cover, weighted average price, contingent right

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

"funded by a "sell to cover" transaction and does not represent a discretionary trade"

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.

contingent right financial

"represents a contingent right to receive one share of the Issuer's common stock"

FAQ

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

What insider equity activity did UPWK’s GM & COO report on September 18, 2026?

UPWK’s GM & COO, Anthony Ray Kappus, reported the vesting and conversion of 114,860 RSUs into common stock, followed by an automatic sale of a portion of those shares to satisfy tax withholding obligations through a mandated “sell to cover” transaction.

How many UPWK restricted stock units vested and converted for Anthony Ray Kappus?

On September 18, 2026, 114,860 restricted stock units vested for Anthony Ray Kappus, each RSU representing a contingent right to receive one share of Upwork common stock, resulting in the acquisition of 114,860 common shares upon conversion.

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

Anthony Ray Kappus sold 45,732 shares of UPWK common stock at a weighted average price of $8.4508 per share. The shares were sold in multiple transactions at prices ranging from $8.315 to $8.52 per share.

Why were UPWK shares sold in this Form 4 for Anthony Ray Kappus?

The 45,732 UPWK shares sold represent stock required to be sold to cover tax withholding obligations related to RSU vesting. The sale was mandated by Upwork’s equity incentive plan as a “sell to cover” transaction and did not represent a discretionary trade by Kappus.

How many UPWK RSUs does Anthony Ray Kappus hold after this transaction?

Following the September 18, 2026 vesting and conversion, Anthony Ray Kappus directly held 344,582 restricted stock units in UPWK, which continue to vest over time subject to his continued employment with the company.

Were the UPWK insider transactions by Anthony Ray Kappus under a Rule 10b5-1 plan?

No. The filing indicates no Rule 10b5-1 trading plan for these transactions. However, the sale of shares was still non-discretionary, as it was required by Upwork’s election to satisfy tax withholding obligations through a mandated “sell to cover” transaction.

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

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Available on EDGAR 09/22/2026 - 04:20 PM Accepted by SEC EDGAR 09/22/2026 - 04:19 PM Learn about SEC filing dates

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)
09/18/2026

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	09/18/2026		M		114,860	A	(1)	122,074	D
Common Stock	09/18/2026		S(2)		45,732	D	$8.4508(3)	76,342	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)	09/18/2026		M			114,860	(4)	(4)	Common Stock	114,860	$0.00	344,582	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 $8.315 to $8.52 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. The RSUs vest 25% on September 18, 2026, and then 1/16th of the total number of shares on each quarterly anniversary thereafter, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	09/22/2026
	** 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)