UPWORK, INC

Insider Trading Arrangements

During the three months ended June 30, 2025, two of our directors or officers (as defined in Section 16a-1(f) under the Exchange Act)adopted, modified, orterminated a “Rule 10b5-1 trading arrangement” or “non-Rule 10b5-1 trading arrangement,” as each term is defined in Item 408 of Regulation S-K, intended to satisfy the affirmative defense of Rule 105b-1(c) under the Exchange Act, each of which is referred to as the Sales Plan, as set forth in the table below.

Each Sales Plan included a representation from the director or officer to the broker administering the plan that such director or officer was not in possession of any material nonpublic information regarding Upwork or the Upwork securities subject to the Sales Plan. A similar representation was made to us in connection with the adoption of each Sales Plan under our Insider Trading Policy. Those representations were made as of the date of adoption or modification of each Sales Plan and speak only as of that date. In making those representations, there is no assurance with respect to any material nonpublic information of which the director or officer was unaware, or with respect to any material nonpublic information acquired by the director, officer, or us after the date of the representation.

(1) The trading arrangement will be in effect until the earlier of (i) the expiration date set forth in the table and (ii) the date on which the maximum number of shares of our common stock subject to the Sales Plan have been sold thereunder.

(2) Includes (i) up to 1,294 shares issued upon the vesting of restricted stock units, which we refer to as RSUs, previously granted to Mr. Marie that vested and were released to Mr. Marie prior to the adoption date, less any such shares that may have previously been sold pursuant to Mr. Marie’s Rule 10b5-1 trading plan adopted on May 3, 2024, (ii) up to 36,597 shares issuable upon the vesting of RSUs previously granted to Mr. Marie that will vest and be released to Mr. Marie on or prior to the retirement date, subject to Mr. Marie’s continued service on each vesting date and less the number of shares sold upon the vesting of the RSUs covered by the Sales Plan to satisfy tax withholding obligations pursuant to Upwork’s non-discretionary “sell to cover” requirement, and (iii) a number of shares Mr. Marie may purchase under the 2018 ESPP during the term of the Sales Plan, which cannot be determined at this time as the purchase price for such shares will be determined at the end of the applicable purchase period under the 2018 ESPP.

(3) Includes (i) up to 187,478 shares issuable upon the vesting of RSUs previously granted to Mr. Bottoms that will vest and be released to Mr. Bottoms on or prior to the expiration date, subject to Mr. Bottoms’s continued service on each vesting date and less the number of shares sold upon the vesting of the RSUs covered by the Sales Plan to satisfy tax withholding obligations pursuant to Upwork’s non-discretionary “sell to cover” requirement, (ii) up to 287,219 shares issuable upon the vesting of performance stock units, which we refer to as PSUs, previously granted to Mr. Bottoms that will vest and be released to Mr. Bottoms on or prior to the expiration date, subject to Upwork’s achievement of the performance criteria applicable to the PSUs and Mr. Bottoms’s continued service on each vesting date and less the number of shares sold upon the vesting of the PSUs covered by the Sales Plan to satisfy tax withholding obligations pursuant to Upwork’s non-discretionary “sell to cover” requirement, and (iii) a number of shares Mr. Bottoms may purchase under the 2018 ESPP during the term of the Sales Plan, which cannot be determined at this time as the purchase price for such shares will be determined at the end of the applicable purchase period under the 2018 ESPP.