Hayden Brown - 13 May 2021 Form 4 Insider Report for UPWORK, INC (UPWK)

Role: President & CEO, Director
Signature: /s/ Jacob McQuown, Attorney-in-Fact
Issuer symbol: UPWK
Transactions as of: 13 May 2021
Net transactions value: -$689,183
Form type: 4
Filing time: 17 May 2021, 16:25:43 UTC
Next filing: 20 May 2021
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	UPWK	Common Sock	Options Exercise	$73,600	+20,000	+3%	$3.68	686,634	13 May 2021	Direct
transaction	UPWK	Common Sock	Sale	$508,588	-13,428	-2%	$37.88	673,206	13 May 2021	Direct	F1, F2
transaction	UPWK	Common Sock	Sale	$218,774	-5,672	-0.84%	$38.57	667,534	13 May 2021	Direct	F1, F3
transaction	UPWK	Common Sock	Sale	$35,421	-900	-0.13%	$39.36	666,634	13 May 2021	Direct	F1, 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	Employee Stock Option (right to buy)	Options Exercise	$0	-20,000	-5%	$0.000000	381,709	13 May 2021	Common Sock	20,000	$3.68	Direct	F5

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

Explanation of Responses:

Id	Content
F1	This transaction was effected pursuant to a Rule 10b5-1 trading plan previously adopted by the Reporting Person.
F2	The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $37.17 to $38.16 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.
F3	The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $38.17 to $39.12 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 $39.20 to $39.55 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 options vested with respect to 1/60th of the total shares on October 26, 2017, and then 1/60th of the total shares vest monthly thereafter, subject to the continuing employment of the Reporting Person on each vesting date.