X0306 4 2019-06-17 0 0001627475 Upwork Inc. UPWK 0001753419 Yuan Han-Shen C/O UPWORK INC. 441 LOGUE AVENUE MOUNTAIN VIEW CA 94043 0 1 0 0 SVP, Engineering Common Stock 2019-06-17 4 M 0 50000 3.18 A 52266 D Common Stock 2019-06-17 4 S 0 50000 15.4544 D 2266 D Common Stock 2019-06-18 4 M 0 50000 3.18 A 52266 D Common Stock 2019-06-18 4 S 0 50000 15.1741 D 2266 D Employee Stock Option (Right to Buy) 3.18 2019-06-17 4 M 0 50000 0 D 2025-09-20 Common Stock 50000 300000 D Employee Stock Option (Right to Buy) 3.18 2019-06-18 4 M 0 50000 0 D 2025-09-20 Common Stock 50000 250000 D The transactions reported on this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the Reporting Person. Includes 2,266 shares acquired under the Issuer's employee stock purchase plan on May 14, 2019. Represents the aggregate of sales effected on the same day at different prices. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.06 to $15.64 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 and became exercisable, and shall continue to vest and become exercisable, with respect to 1/5th of the shares on June 16, 2016, and an additional 1/60th of the shares monthly thereafter, subject to the continuing employment of the Reporting Person on each vesting date. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $15.025 to $15.63 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. /s/ Jacob McQuown, Attorney-in-Fact 2019-06-19