Eric Gilpin - May 18, 2021 Form 4 Insider Report for UPWORK, INC (UPWK)

Role: Senior VP, Sales
Signature: /s/ Jacob McQuown, Attorney-in-Fact
Stock symbol: UPWK
Transactions as of: May 18, 2021
Transactions value $: -$133,507
Form type: 4
Date filed: 5/20/2021, 07:12 PM
Next filing: Aug 20, 2021

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPWK	Common Stock	Options Exercise		+6.74K	+83.17%		14.8K	May 18, 2021	Direct	F1, F2
transaction	UPWK	Common Stock	Options Exercise		+525	+3.54%		15.4K	May 18, 2021	Direct	F1
transaction	UPWK	Common Stock	Sale	-$124K	-3.08K	-20.02%	$40.27	12.3K	May 18, 2021	Direct	F3, F4
transaction	UPWK	Common Stock	Sale	-$9.68K	-240	-1.95%	$40.32	12K	May 18, 2021	Direct	F3, F4

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-6.74K	-8.33%	$0.00	74.1K	May 18, 2021	Common Stock	6.74K		Direct	F1, F5
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-525	-6.24%	$0.00	7.89K	May 18, 2021	Common Stock	525		Direct	F1, F6

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock.
F2	Includes 1,065 shares acquired under the Issuer's employee stock purchase plan on May 14, 2021.
F3	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.
F4	The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $40.10 to $40.90 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 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.
F6	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.