Upwork (NASDAQ: UPWK) CFO vests RSUs and sells shares to cover taxes

Rhea-AI Filing Summary

UPWORK, INC Chief Financial Officer Erica Gessert reported routine equity compensation activity involving RSUs and a related tax sale. On June 18 2026, 18,132 restricted stock units converted into the same number of common shares. To cover tax withholding on this vesting, 9,169 common shares were sold in a mandated “sell to cover” transaction at a weighted average price of $8.1507 per share, with actual sale prices ranging from $8.02 to $8.25 per share. The filing notes this sale did not represent a discretionary trade by Gessert. Following these transactions, she directly holds 341,609 shares of Upwork common stock. The RSU awards continue to vest in equal quarterly installments over four years beginning on June 18, 2024 and June 18, 2025, subject to her continued employment.

Insights

Equity compensation analyst

Routine RSU vesting with tax-related share sale; limited signaling value.

The transactions show Erica Gessert receiving common shares as her restricted stock units vested and then selling a portion solely to fund tax withholding. Footnotes specify the company requires a mandated “sell to cover” under its equity incentive plans.

This pattern—derivative exercises combined with a tax-driven sale—typically reflects mechanics of equity compensation rather than an active market-timing decision. Net, she remains a substantial shareholder with 341,609 common shares held directly after the transactions.

The RSUs vest in equal quarterly installments over four years starting on June 18, 2024 and June 18, 2025, so similar non-discretionary tax sales may recur as future tranches vest, depending on withholding requirements.

Insider Trade Summary

Net Seller: 9,169 shares ($74,734)

Net Sell 5 txns

Insider Gessert Erica

Role Chief Financial Officer

Sold 9,169 shs ($75K)

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units	8,432	$0.00	--
Exercise	Restricted Stock Units	9,700	$0.00	--
Exercise	Common Stock	8,432	$0.00	--
Exercise	Common Stock	9,700	$0.00	--
Sale	Common Stock	9,169	$8.1507	$75K

Holdings After Transaction: Restricted Stock Units — 59,031 shares (Direct, null); Common Stock — 341,078 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 $8.02 to $8.25 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 June 18, 2024, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date. The RSUs vest in equal quarterly installments over four years beginning on June 18, 2025, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Key Figures

Shares sold for taxes: 9,169 shares Weighted average sale price: $8.1507 per share RSUs converted: 18,132 units +2 more

5 metrics

Shares sold for taxes 9,169 shares Mandated sell-to-cover on June 18 2026

Weighted average sale price $8.1507 per share Open-market sale for tax withholding

RSUs converted 18,132 units Restricted stock units converting into common shares

Common shares held after 341,609 shares Direct ownership after June 18 2026 transactions

Sale price range $8.02–$8.25 per share Price range for multiple sale executions

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

"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.

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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^*

Gessert Erica

(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)
	Chief Financial Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/18/2026

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	06/18/2026		M		8,432	A	(1)	341,078	D
Common Stock	06/18/2026		M		9,700	A	(1)	350,778	D
Common Stock	06/18/2026		S(2)		9,169	D	$8.1507(3)	341,609	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)	06/18/2026		M			8,432	(4)	(4)	Common Stock	8,432	$0.00	59,031	D
Restricted Stock Units	(1)	06/18/2026		M			9,700	(5)	(5)	Common Stock	9,700	$0.00	106,697	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 $8.02 to $8.25 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 June 18, 2024, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

5. The RSUs vest in equal quarterly installments over four years beginning on June 18, 2025, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

Remarks:

	/s/ Jacob McQuown, Attorney-in-Fact	06/23/2026
	** 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 did Upwork (UPWK) CFO Erica Gessert report in this Form 4?

Erica Gessert reported RSU vesting and a related tax sale. On June 18 2026, 18,132 restricted stock units converted into common shares, and 9,169 shares were sold to cover tax withholding obligations mandated under Upwork’s equity incentive plans.

How many Upwork (UPWK) shares did the CFO sell and at what price?

The CFO sold 9,169 Upwork common shares. The weighted average sale price was $8.1507 per share, with individual trades executed between $8.02 and $8.25 per share, according to the weighted-average price footnote in the filing.

Was Erica Gessert’s Upwork (UPWK) share sale a discretionary trade?

No, the filing states the sale was not discretionary. Shares were sold under a mandated “sell to cover” arrangement chosen by Upwork to satisfy tax withholding on RSU vesting, so the transaction reflects tax obligations rather than an elective market-timing decision.

How many Upwork (UPWK) shares does the CFO hold after these transactions?

After the reported transactions, Gessert holds 341,609 common shares directly. This post-transaction balance, disclosed in the Form 4, shows she retains a sizable equity position in Upwork following the RSU conversion and related tax-driven share sale.

How do the Upwork (UPWK) CFO’s RSUs vest over time?

The RSUs vest in equal quarterly installments over four years. One grant began vesting on June 18, 2024 and another on June 18, 2025, with continued vesting conditioned on Gessert’s ongoing employment with Upwork at each quarterly vesting date.

What do the restricted stock units (RSUs) in the Upwork (UPWK) filing represent?

Each RSU represents a right to receive one Upwork common share. As RSUs vest, they convert into an equal number of common shares that are delivered to the holder, subject to applicable tax withholding and the company’s equity incentive plan provisions.