UPWORK, INC — Director's Dealing 2023

Feb 23, 2023

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: UPWORK, INC (UPWK)
CIK: 0001627475
Period of Report: 2023-02-18

Reporting Person: Gilpin Eric (Chief Sales Officer)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2023-02-18	Common Stock	M	6735	—	Acquired	45973	Direct
2023-02-18	Common Stock	M	263	—	Acquired	46236	Direct
2023-02-18	Common Stock	M	526	—	Acquired	46762	Direct
2023-02-18	Common Stock	M	8790	—	Acquired	55552	Direct
2023-02-18	Common Stock	M	3924	—	Acquired	59476	Direct
2023-02-18	Common Stock	M	3043	—	Acquired	62519	Direct
2023-02-21	Common Stock	S	11331	$11.4666	Disposed	51188	Direct

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2023-02-18	Restricted Stock Units (RSU)	$	A	35159	Acquired		Common Stock (35159)	Direct
2023-02-18	Restricted Stock Units (RSU)	$	A	40000	Acquired		Common Stock (40000)	Direct
2023-02-18	Restricted Stock Units (RSU)	$	M	6735	Disposed		Common Stock (6735)	Direct
2023-02-18	Restricted Stock Units (RSU)	$	M	263	Disposed		Common Stock (263)	Direct
2023-02-18	Restricted Stock Units (RSU)	$	M	526	Disposed		Common Stock (526)	Direct
2023-02-18	Restricted Stock Units (RSU)	$	M	8790	Disposed		Common Stock (8790)	Direct
2023-02-18	Restricted Stock Units (RSU)	$	M	3924	Disposed		Common Stock (3924)	Direct
2023-02-18	Restricted Stock Units (RSU)	$	M	3043	Disposed		Common Stock (3043)	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 $11.38 to $11.62 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 RSUs vest 25% on February 18, 2023, and then 6.25% of the total shares vest on each quarterly anniversary thereafter, subject to the Reporting Person's continued employment with the Issuer on each vesting date.

F5: The RSUs vest in equal quarterly installments over four years beginning on May 18, 2023, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

F6: The RSUs vest in equal quarterly installments over four years beginning on May 18, 2020, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

F7: The RSUs vest 25% on February 18, 2022, and then 6.25% of the total shares vest on each quarterly anniversary thereafter, subject to the Reporting Person's continued employment with the Issuer on each vesting date.

F8: The RSUs vest in equal quarterly installments over four years beginning on May 18, 2021, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

F9: The RSUs vest in equal quarterly installments over four years beginning on May 18, 2022, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.

F10: The RSUs vest in equal quarterly installments on each quarterly anniversary, beginning on November 18, 2022 over four quarters of continuous service, subject to the continuing employment of the Reporting Person with the Issuer on each vesting date.