Eric Gilpin - Feb 18, 2023 Form 4 Insider Report for UPWORK, INC (UPWK)

Role
Chief Sales Officer
Signature
/s/ Jacob McQuown, Attorney-in-Fact
Stock symbol
UPWK
Transactions as of
Feb 18, 2023
Transactions value $
-$129,928
Form type
4
Date filed
2/22/2023, 07:35 PM
Previous filing
Nov 22, 2022

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction UPWK Common Stock Options Exercise +6.74K +17.16% 46K Feb 18, 2023 Direct F1
transaction UPWK Common Stock Options Exercise +263 +0.57% 46.2K Feb 18, 2023 Direct F1
transaction UPWK Common Stock Options Exercise +526 +1.14% 46.8K Feb 18, 2023 Direct F1
transaction UPWK Common Stock Options Exercise +8.79K +18.8% 55.6K Feb 18, 2023 Direct F1
transaction UPWK Common Stock Options Exercise +3.92K +7.06% 59.5K Feb 18, 2023 Direct F1
transaction UPWK Common Stock Options Exercise +3.04K +5.12% 62.5K Feb 18, 2023 Direct F1
transaction UPWK Common Stock Sale -$130K -11.3K -18.12% $11.47 51.2K Feb 21, 2023 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) Award $0 +35.2K $0.00 35.2K Feb 18, 2023 Common Stock 35.2K Direct F1, F4
transaction UPWK Restricted Stock Units (RSU) Award $0 +40K $0.00 40K Feb 18, 2023 Common Stock 40K Direct F1, F5
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -6.74K -20% $0.00 26.9K Feb 18, 2023 Common Stock 6.74K Direct F1, F6
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -263 -11.18% $0.00 2.09K Feb 18, 2023 Common Stock 263 Direct F1, F7
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -526 -11.12% $0.00 4.21K Feb 18, 2023 Common Stock 526 Direct F1, F8
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -8.79K -25% $0.00 26.4K Feb 18, 2023 Common Stock 8.79K Direct F1, F4
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -3.92K -7.69% $0.00 47.1K Feb 18, 2023 Common Stock 3.92K Direct F1, F9
transaction UPWK Restricted Stock Units (RSU) Options Exercise $0 -3.04K -33.33% $0.00 6.09K Feb 18, 2023 Common Stock 3.04K Direct F1, F10
* 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 $11.38 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.