Eric Gilpin - 18 May 2022 Form 4 Insider Report for UPWORK, INC (UPWK)

Signature
/s/ Jacob McQuown, Attorney-in-Fact
Issuer symbol
UPWK
Transactions as of
18 May 2022
Net transactions value
-$88,512
Form type
4
Filing time
20 May 2022, 19:03:29 UTC
Previous filing
24 Feb 2022
Next filing
22 Aug 2022

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction UPWK Common Stock Options Exercise +6,734 +34% 26,631 18 May 2022 Direct F1, F2
transaction UPWK Common Stock Options Exercise +261 +0.98% 26,892 18 May 2022 Direct F1
transaction UPWK Common Stock Options Exercise +526 +2% 27,418 18 May 2022 Direct F1
transaction UPWK Common Stock Options Exercise +3,924 +14% 31,342 18 May 2022 Direct F1
transaction UPWK Common Stock Sale $88,512 -5,509 -18% $16.07 25,833 18 May 2022 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 -6,734 -12% $0.000000 47,145 18 May 2022 Common Stock 6,734 Direct F1, F5
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -261 -8.3% $0.000000 2,877 18 May 2022 Common Stock 261 Direct F1, F6
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -526 -8.3% $0.000000 5,782 18 May 2022 Common Stock 526 Direct F1, F7
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -3,924 -6.2% $0.000000 58,861 18 May 2022 Common Stock 3,924 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 Includes 555 shares acquired under the Issuer's employee stock purchase plan on May 13, 2022.
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 $15.94 to $16.31 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 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.
F7 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.
F8 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.