Dave Bottoms - 18 Sep 2025 Form 4 Insider Report for UPWORK, INC (UPWK)

Role
GM, Marketplace
Signature
/s/ Jacob McQuown, Attorney-in-Fact
Issuer symbol
UPWK
Transactions as of
18 Sep 2025
Net transactions value
-$408,647
Form type
4
Filing time
22 Sep 2025, 16:33:59 UTC
Previous filing
03 Sep 2025
Next filing
19 Nov 2025
SEC
View on sec.gov

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
Bottoms Dave GM, Marketplace C/O UPWORK INC., 530 LYTTON AVENUE, SUITE 301, PALO ALTO /s/ Jacob McQuown, Attorney-in-Fact 22 Sep 2025 0002019194

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction UPWK Common Stock Options Exercise +8,980 +2603% 9,325 18 Sep 2025 Direct F1
transaction UPWK Common Stock Options Exercise +6,024 +65% 15,349 18 Sep 2025 Direct F1
transaction UPWK Common Stock Options Exercise +5,904 +38% 21,253 18 Sep 2025 Direct F1
transaction UPWK Common Stock Sale $208,779 -10,894 -51% $19.16 10,359 18 Sep 2025 Direct F2, F3
transaction UPWK Common Stock Sale $199,867 -10,014 -97% $19.96 345 19 Sep 2025 Direct F4, F5

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction UPWK Restricted Stock Units Options Exercise $0 -8,980 -20% $0.000000 35,920 18 Sep 2025 Common Stock 8,980 Direct F1, F6
transaction UPWK Restricted Stock Units Options Exercise $0 -6,024 -9.1% $0.000000 60,235 18 Sep 2025 Common Stock 6,024 Direct F1, F7
transaction UPWK Restricted Stock Units Options Exercise $0 -5,904 -6.7% $0.000000 82,658 18 Sep 2025 Common Stock 5,904 Direct F1, F8
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Buy Plan / Sale Plan: These are also open market purchases/sales of shares, but in this case the transaction is part of a trading plan. Rule 10b5-1 allows insiders to setup a trading plan to buy/sell stocks over a certain period of time. Since the purchases/sales are predetermined, this protects the insiders from violating insider trading law.

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).

Explanation of Responses:

Id Content
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 $18.89 to $19.495 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 This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on May 30, 2025.
F5 The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $19.64 to $20.35 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.
F6 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.
F7 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.
F8 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.