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UPWORK, INC Director's Dealing 2025

Nov 20, 2025

31644_dirs_2025-11-19_aa9dad3d-e64b-46df-b6bd-b26dc23cdc26.zip

Director's Dealing

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SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: UPWORK, INC (UPWK)
CIK: 0001627475
Period of Report: 2025-11-17

Reporting Person: Bottoms Dave (N/A)

Non-Derivative Transactions

Date Security Code Shares Price A/D Holdings After Ownership
2025-11-17 Common Stock S 561.00 $16.45 Disposed 345.00 Direct
2025-11-18 Common Stock M 3750.00 Acquired 4095.00 Direct
2025-11-18 Common Stock S 955.00 $16.1426 Disposed 3140.00 Direct
2025-11-18 Common Stock S 1047.00 $17.2393 Disposed 2093.00 Direct
2025-11-19 Common Stock S 1748.00 $18.1293 Disposed 345.00 Direct

Derivative Transactions

Date Security Exercise Price Code Shares A/D Expiration Underlying Ownership
2025-11-18 Restricted Stock Units $ M 3750.00 Disposed Common Stock (3750.00) Direct

Footnotes

F1: This transaction was effected pursuant to a Rule 10b5-1 plan adopted by the Reporting Person on May 30, 2025.

F2: Reflects 561 shares acquired under the Issuer's employee stock purchase plan on November 14, 2025.

F3: Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.

F4: 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.

F5: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.66 to $16.65 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $16.67 to $17.4932 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.

F7: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $17.80 to $18.36 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.

F8: The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.