Was Hayden Brown’s Upwork (UPWK) share sale a discretionary transaction?

The filing states the sale was not discretionary. Shares were sold under a mandated “sell to cover” arrangement to satisfy tax withholding obligations tied to RSU vesting, as required by Upwork’s equity incentive plan election.

Upwork (UPWK) CEO Hayden Brown exercises RSUs, sells 23,745 shares to cover taxes

Filing Impact

(Neutral)

Filing Sentiment

(Neutral)

Form Type

Rhea-AI Filing Summary

UPWORK, INC President & CEO Hayden Brown reported routine equity compensation activity. On March 18, 2026, Brown exercised restricted stock units that converted into a total of 46,410 shares of common stock at an exercise price of $0.00 per share.

To cover tax withholding obligations from these RSU vestings, 23,745 shares of common stock were sold in a mandated “sell to cover” transaction at a weighted average price of $12.3118 per share, which the footnotes state was not a discretionary trade. Following these transactions, Brown directly owned 798,732 shares of Upwork common stock. The RSUs vest in equal quarterly installments over four years beginning on June 18, 2024 and June 18, 2025, subject to continued employment.

Insider Trade Summary

Net Seller: 23,745 shares ($292,344)

Net Sell 5 txns

Insider Brown Hayden

Role President & CEO

Sold 23,745 shs ($292K)

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units	17,733	$0.00	--
Exercise	Restricted Stock Units	28,677	$0.00	--
Exercise	Common Stock	17,733	$0.00	--
Exercise	Common Stock	28,677	$0.00	--
Sale	Common Stock	23,745	$12.3118	$292K

Holdings After Transaction: Restricted Stock Units — 141,866 shares (Direct); Common Stock — 793,800 shares (Direct)

Footnotes (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 $12.13 to $12.52 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. 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.

Form 4 Insider Transactions: What Each Field Means →

03/20/2026 - 04:50 PM

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^*

Brown Hayden

(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)

X	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	President & CEO

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
03/18/2026

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	03/18/2026		M		17,733	A	⁽¹⁾	793,800	D
Common Stock	03/18/2026		M		28,677	A	⁽¹⁾	822,477	D
Common Stock	03/18/2026		S⁽²⁾		23,745	D	$12.3118⁽³⁾	798,732	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⁾	03/18/2026		M			17,733	⁽⁴⁾	⁽⁴⁾	Common Stock	17,733	$0.00	141,866	D
Restricted Stock Units	⁽¹⁾	03/18/2026		M			28,677	⁽⁵⁾	⁽⁵⁾	Common Stock	28,677	$0.00	344,130	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 $12.13 to $12.52 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 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	03/20/2026
	** 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

FAQ

What insider transactions did Upwork (UPWK) CEO Hayden Brown report?

Hayden Brown reported RSU vesting and related share activity. RSUs converted into 46,410 common shares, and 23,745 shares were sold to cover tax withholding, leaving her with 798,732 directly owned Upwork shares after the transactions.

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

The filing shows 23,745 Upwork common shares sold. The weighted average sale price was $12.3118 per share, with individual trades executed between $12.13 and $12.52, according to the detailed price range disclosed in the footnotes.

How many Upwork (UPWK) shares does the CEO hold after these Form 4 transactions?

After the reported RSU exercises and tax-related sale, Hayden Brown directly holds 798,732 shares of Upwork common stock. This figure reflects her post-transaction ownership as disclosed in the non-derivative holdings section of the Form 4.

What RSU vesting schedule applies to Upwork (UPWK) CEO Hayden Brown?

The RSUs referenced in the filing vest in equal quarterly installments over four years. One grant begins vesting on June 18, 2024, and another on June 18, 2025, each conditioned on Hayden Brown’s continued employment with Upwork.

How many RSUs did Upwork (UPWK) CEO Hayden Brown have convert into common shares?

Two RSU tranches converted, totaling 46,410 underlying shares of Upwork common stock. One tranche covered 17,733 shares and the other 28,677 shares, each RSU representing a contingent right to receive one share of common stock.