X0306 4 2021-03-04 0 0001627475 Upwork Inc. UPWK 0001753662 Brown Hayden C/O UPWORK INC. 2625 AUGUSTINE DRIVE, SUITE 601 SANTA CLARA CA 95054 1 1 0 0 President & CEO Common Sock 2021-03-04 4 M 0 2501 3.67 A 441405 D Common Sock 2021-03-04 4 M 0 76755 3.58 A 518160 D Common Sock 2021-03-04 4 M 0 3333 3.03 A 521493 D Common Sock 2021-03-04 4 M 0 177411 3.68 A 698904 D Common Sock 2021-03-04 4 S 0 15504 42.4661 D 683400 D Common Sock 2021-03-04 4 S 0 79418 43.5098 D 603982 D Common Sock 2021-03-04 4 S 0 38759 44.4135 D 565223 D Common Sock 2021-03-04 4 S 0 97756 45.1926 D 467467 D Common Sock 2021-03-04 4 S 0 28563 46.0699 D 438904 D Employee Stock Option (right to buy) 3.67 2021-03-04 4 M 0 2501 0.00 D 2024-12-18 Common Stock 2501 13141 D Employee Stock Option (right to buy) 3.58 2021-03-04 4 M 0 76755 0.00 D 2025-04-22 Common Sock 76755 1359 D Employee Stock Option (right to buy) 3.03 2021-03-04 4 M 0 3333 0.00 D 2025-12-22 Common Sock 3333 41668 D Employee Stock Option (right to buy) 3.68 2021-03-04 4 M 0 177411 0.00 D 2027-09-25 Common Sock 177411 401709 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 $41.88 to $42.875 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 $42.88 to $43.87 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 $43.88 to $44.875 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 $44.88 to $45.87 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 $45.88 to $46.46 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 options vested with respect to 1/60th of the total shares on January 19, 2015, 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 options vested with respect of 1/60th of the total shares on May 15, 2015, 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 contains an early-exercise provision and is exercisable as to unvested shares, subject to the Issuer's right of repurchase. The options vested with respect of 1/60th of the total shares on February 1, 2016, 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 options vested with respect to 1/60th of the total shares on October 26, 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. /s/ Jacob McQuown, Attorney-in-Fact 2021-03-08