X0306 4 2021-05-13 0 0001627475 UPWORK, INC UPWK 0001753662 Brown Hayden C/O UPWORK INC., 475 BRANNAN STREET, SUITE 430 SAN FRANCISCO CA 94107 1 1 0 0 President & CEO Common Sock 2021-05-13 4 M 0 20000 3.68 A 686634 D Common Sock 2021-05-13 4 S 0 13428 37.8752 D 673206 D Common Sock 2021-05-13 4 S 0 5672 38.5709 D 667534 D Common Sock 2021-05-13 4 S 0 900 39.3567 D 666634 D Employee Stock Option (right to buy) 3.68 2021-05-13 4 M 0 20000 0.00 D 2027-09-25 Common Sock 20000 381709 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 $37.17 to $38.16 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 $38.17 to $39.12 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 $39.20 to $39.55 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 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 2021-05-17