Upwork GM Executes $156K Stock Sale for Tax Obligations

Accepted by SEC EDGAR 06/23/2025 - 07:22 PM EDT

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Form Type

Rhea-AI Filing Summary

Dave Bottoms, GM of Marketplace at Upwork, reported multiple transactions on June 18, 2025, involving Restricted Stock Units (RSUs) and common stock:

Acquired 20,907 shares through the conversion of RSUs in three tranches: 8,980, 6,023, and 5,904 shares
Sold 11,562 shares at weighted average price of $13.51 to cover tax withholding obligations
Retained 9,345 shares after the transactions

The transactions were part of scheduled RSU vestings with different vesting schedules starting from December 2022, June 2024, and June 2025, each vesting quarterly over four years. The share sale was mandatory under Upwork's equity incentive plan for tax withholding through a "sell to cover" transaction, not a discretionary trade by the executive.

Insider Trade Summary

Exercise and sale activity reported; no spread calculated

Exercise and Sale 7 txns

Insider Bottoms Dave

Role GM, Marketplace

Sold 11,562 shs ($156K)

Approx. gross sale proceeds $156K

Approx. exercise cost $0.00

Type	Security	Shares	Price	Value
Exercise	Restricted Stock Units	8,980	$0.00	$0.00
Exercise	Restricted Stock Units	6,023	$0.00	$0.00
Exercise	Restricted Stock Units	5,904	$0.00	$0.00
Exercise	Common Stock	8,980	$0.00	$0.00
Exercise	Common Stock	6,023	$0.00	$0.00
Exercise	Common Stock	5,904	$0.00	$0.00
Sale	Common Stock	11,562	$13.5054	$156K

Holdings After Transaction: Restricted Stock Units — 199,721 contracts (Direct); Common Stock — 9,345 shares (Direct)

Footnotes (6)

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 $13.24 to $13.73 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 December 18, 2022, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.
F5. 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.
F6. 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.

FAQ

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

How many UPWK shares did GM Dave Bottoms sell on June 18, 2025?

Dave Bottoms sold 11,562 shares of UPWK common stock on June 18, 2025 at a weighted average price of $13.5054 per share. This sale was specifically to cover tax withholding obligations related to RSU vesting and was not a discretionary trade.

What was the vesting schedule for UPWK's RSUs granted to Dave Bottoms?

Dave Bottoms had three different RSU grants with different vesting schedules: 1) RSUs vesting quarterly over 4 years beginning December 18, 2022, 2) RSUs vesting quarterly over 4 years beginning June 18, 2024, and 3) RSUs vesting quarterly over 4 years beginning June 18, 2025.

How many UPWK shares does Dave Bottoms own after the June 18, 2025 transactions?

After the reported transactions, Dave Bottoms directly owns 9,345 shares of UPWK common stock. Additionally, he holds 44,900, 66,259, and 88,562 unvested RSUs from three different grants.

What was the price range of UPWK shares sold in the June 18, 2025 transaction?

The UPWK shares were sold in multiple transactions at prices ranging from $13.24 to $13.73 per share, with a weighted average price of $13.5054 per share.

What is Dave Bottoms' position at UPWK?

Dave Bottoms serves as GM, Marketplace at Upwork Inc. (UPWK) as indicated in the Form 4 filing.

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Form 4 Insider Transactions: What Each Field Means →

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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^*

Bottoms Dave

(Last)

(First)

(Middle)

C/O UPWORK INC.

530 LYTTON AVENUE, SUITE 301

(Street)

PALO ALTO

94301

(City)

(State)

(Zip)

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, Marketplace

3. Date of Earliest Transaction (Month/Day/Year)
06/18/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

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	06/18/2025		M		8,980	A	⁽¹⁾	8,980	D
Common Stock	06/18/2025		M		6,023	A	⁽¹⁾	15,003	D
Common Stock	06/18/2025		M		5,904	A	⁽¹⁾	20,907	D
Common Stock	06/18/2025		S⁽²⁾		11,562	D	$13.5054⁽³⁾	9,345	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⁾	06/18/2025		M			8,980	⁽⁴⁾	⁽⁴⁾	Common Stock	8,980	$0.00	44,900	D
Restricted Stock Units	⁽¹⁾	06/18/2025		M			6,023	⁽⁵⁾	⁽⁵⁾	Common Stock	6,023	$0.00	66,259	D
Restricted Stock Units	⁽¹⁾	06/18/2025		M			5,904	⁽⁶⁾	⁽⁶⁾	Common Stock	5,904	$0.00	88,562	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 $13.24 to $13.73 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 December 18, 2022, 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, 2024, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

6. 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	06/23/2025
	** 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.

Source: View Original Filing on SEC EDGAR