UPWORK, INC — Director's Dealing 2021

Jan 21, 2021

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: Upwork Inc. (UPWK)
CIK: 0001627475
Period of Report: 2021-01-18

Reporting Person: Brown Hayden (Director, President & CEO)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2021-01-18	Common Stock	M	2585	—	Acquired	439971	Direct
2021-01-20	Common Stock	S	633	$39.866	Disposed	439338	Direct
2021-01-20	Common Stock	S	354	$40.7498	Disposed	438984	Direct
2021-01-20	Common Stock	S	80	$41.3537	Disposed	438904	Direct

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2021-01-18	Employee Stock Option (right to buy)	$38.80	A	1500000	Acquired	2031-01-17	Common Stock (1500000)	Direct
2021-01-18	Restricted Stock Units (RSU)	$	M	2585	Disposed		Common Stock (2585)	Direct

Footnotes

F1: Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.

F2: 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.

F3: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $39.27 to $40.26 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.

F4: The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $40.27 to $41.26 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.

F5: The reported price in Column 4 is a weighted average price. These shares were purchased in multiple transactions at prices ranging from $41.27 to $41.74 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 purchased at each separate price within the range set forth in this footnote.

F6: The option will vest in 16 equal quarterly installments conditioned upon the achievement of certain performance milestones that are based on market capitalization metrics, subject to the Reporting Person's continued employment as the Chief Executive Officer of the Issuer.

F7: The RSUs will vest in equal quarterly installments over three years beginning on January 18, 2020, subject to the Reporting Person's continuing employment with the Issuer on each vesting date.