X0306 4 2019-05-10 0 0001627475 Upwork Inc. UPWK 0001753417 Kasriel Stephane C/O UPWORK INC. 441 LOGUE AVENUE MOUNTAIN VIEW CA 94043 1 1 0 0 President & CEO Common Stock 2019-05-10 4 M 0 280000 2.76 A 481848 D Common Stock 2019-05-10 4 S 0 209863 16.1999 D 271985 D Common Stock 2019-05-10 4 S 0 70137 16.7848 D 201848 D Common Stock 18152 D Employee Stock Option (right to buy) 2.76 2019-05-10 4 M 0 9225 0 D 2024-04-06 Common Stock 9225 9225 D Employee Stock Option (right to buy) 2.76 2019-05-10 4 M 0 270775 0 D 2024-04-06 Common Stock 270775 301966 D The transactions reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the Reporting Person. Represents the aggregate of sales effected on the same day at different prices. Represents the weighted average sales price per share. The shares sold at prices ranging from $15.68 to $16.65 per share. Full information regarding the number of shares sold at each price shall be provided upon request to the staff of the U.S. Securities and Exchange Commission, the Issuer, or a security holder of the Issuer. Represents the weighted average sales price per share. The shares sold at prices ranging from $16.69 to $16.89 per share. Full information regarding the number of shares sold at each price shall be provided upon request to the staff of the U.S. Securities and Exchange Commission, the Issuer, or a security holder of the Issuer. Held directly by the Reporting Person as custodian for his children. The stock option is fully vested and immediately exercisable. /s/ Jacob McQuown, Attorney-in-Fact 2019-05-14