Jeff McCombs - 18 Nov 2022 Form 4 Insider Report for UPWORK, INC (UPWK)

Role: Chief Financial Officer
Signature: /s/ Jacob McQuown, Attorney-in-Fact
Issuer symbol: UPWK
Transactions as of: 18 Nov 2022
Net transactions value: -$197,527
Form type: 4
Filing time: 22 Nov 2022, 19:02:25 UTC
Previous filing: 03 Oct 2022
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPWK	Common Stock	Options Exercise		+17,146	+20%		101,255	18 Nov 2022	Direct	F1
transaction	UPWK	Common Stock	Options Exercise		+732	+0.72%		101,987	18 Nov 2022	Direct	F1
transaction	UPWK	Common Stock	Options Exercise		+1,472	+1.4%		103,459	18 Nov 2022	Direct	F1
transaction	UPWK	Common Stock	Options Exercise		+7,135	+6.9%		110,594	18 Nov 2022	Direct	F1
transaction	UPWK	Common Stock	Options Exercise		+3,042	+2.8%		113,636	18 Nov 2022	Direct	F1
transaction	UPWK	Common Stock	Sale	$197,527	-16,372	-14%	$12.06	97,264	21 Nov 2022	Direct	F2, F3

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	-17,146	-12%	$0.000000	120,028	18 Nov 2022	Common Stock	17,146		Direct	F1, F4
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-732	-10%	$0.000000	6,592	18 Nov 2022	Common Stock	732		Direct	F1, F5
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-1,472	-10%	$0.000000	13,247	18 Nov 2022	Common Stock	1,472		Direct	F1, F6
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-7,135	-7.1%	$0.000000	92,751	18 Nov 2022	Common Stock	7,135		Direct	F1, F7
transaction	UPWK	Restricted Stock Units (RSU)	Options Exercise	$0	-3,042	-25%	$0.000000	9,129	18 Nov 2022	Common Stock	3,042		Direct	F1, F8

* 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	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 $11.67 to $12.35 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	Pursuant to the Transition and Separation Agreement entered into by and between the Issuer and the Reporting Person dated as of September 21, 2022, 17,146 of the shares initially subject to the restricted stock unit award granted to the Reporting Person on August 4, 2020 accelerated and became fully vested as of November 18, 2022.
F5	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.
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.
F7	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.
F8	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.