X0306 4 2020-11-06 0 0001627475 Upwork Inc. UPWK 0001809355 Gilpin Eric C/O UPWORK INC. 2625 AUGUSTINE DRIVE, SUITE 601 SANTA CLARA CA 95054 0 1 0 0 Senior VP, Sales Common Stock 2020-11-06 4 M 0 40000 3.23 A 42606 D Common Stock 2020-11-06 4 M 0 50000 4.04 A 92606 D Common Stock 2020-11-06 4 S 0 14924 27.7941 D 77682 D Common Stock 2020-11-06 4 S 0 64853 28.5352 D 12829 D Common Stock 2020-11-06 4 S 0 10223 29.2602 D 2606 D Common Stock 2020-11-10 4 M 0 10000 3.23 A 12606 D Common Stock 2020-11-10 4 S 0 1000 25.975 D 11606 D Common Stock 2020-11-10 4 S 0 8500 27.2614 D 3106 D Common Stock 2020-11-10 4 S 0 500 27.912 D 2606 D Employee Stock Option (right to buy) 3.23 2020-11-06 4 M 0 40000 0.00 D 2026-04-19 Common Stock 40000 180000 D Employee Stock Option (right to buy) 4.04 2020-11-06 4 M 0 50000 0.00 D 2028-02-05 Common Stock 50000 50000 D Employee Stock Option (right to buy) 3.23 2020-11-10 4 M 0 10000 0.00 D 2026-04-19 Common Stock 10000 170000 D This transaction was effected pursuant to a Rule 10b5-1 trading plan previously adopted 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 $27.17 to $28.15 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $28.19 to $29.18 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $29.19 to $29.40 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $25.50 to $26.37 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $26.60 to $27.54 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 reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $27.61 to $28.34 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 stock option vested with respect to 1/5th of the total shares on April 20, 2017, and then 1/60th of the total shares vest monthly thereafter, subject to the continuing employment of the Reporting Person on each vesting date. The stock option vested with respect to 1/60th of the total shares on March 6, 2018, and then 1/60th of the total shares vest monthly thereafter, subject to the continuing employment of the Reporting Person on each vesting date. /s/ Jacob McQuown, Attorney-in-Fact 2020-11-10