X0306 4 2019-06-18 0 0001627475 Upwork Inc. UPWK 0001753662 Brown Hayden C/O UPWORK INC. 441 LOGUE AVENUE MOUNTAIN VIEW CA 94043 0 1 0 0 Chief Marketing & Product Ofcr Common Stock 2019-06-18 4 M 0 3860 0 A 295516 D Common Stock 2019-06-18 4 S 0 1435 15.57 D 294081 D Restricted Stock Units (RSU) 2019-06-18 4 M 0 3860 0 D Common Stock 3860 57900 D Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock. Represents the number of shares required to be sold by the Reporting Person to cover tax withholding obligations in connection with the vesting of the RSUs listed in Table II. This sale is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of tax withholding obligations to be funded by a "sell to cover" transaction and does not represent a discretionary trade by the Reporting Person. 6.25% of the RSUs vested on June 18, 2019, and the remainder will vest as to an additional 6.25% of the RSUs on each quarterly anniversary thereafter, subject to, on each vesting date, the Reporting Person's (i) continued employment with the Issuer and (ii) continued leadership of the Issuer's marketing and product departments. Shares of the Issuer's common stock will be delivered to the Reporting Person following vesting. /s/ Jacob McQuown, Attorney-in-Fact 2019-06-20