UPWORK INC

Amended and Restated Change in Control and Severance Agreement

On May 2, 2025, we entered into an amended and restated change in control and severance agreement with David T. Bottoms, our GM, Marketplace, which we refer to as the A&R Severance Agreement. The A&R Severance Agreement provides for, among other changes, (i) an increase in the cash severance benefit from 0.5x to 1.0x base salary and (ii) an increase in the continuation of medical benefits from 6 months to 12 months in the event of Mr. Bottoms’s termination by us without cause (as defined in the A&R Severance Agreement) outside of a change in control (as defined in the A&R Severance Agreement).

The foregoing description of the A&R Severance Agreement is qualified in its entirety by reference to the full text of the A&R Severance Agreement, which will be filed as an exhibit to our Quarterly Report on Form 10-Q for the fiscal quarter ending June 30, 2025.

Insider Trading Arrangements

During the three months ended March 31, 2025, one 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, which is referred to as the Sales Plan, as set forth in the table below.

The Sales Plan included a representation from Ms. Srinivasan to the broker administering the plan that she 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 the Sales Plan under our Insider Trading Policy. Those representations were made as of the date of adoption or modification of the 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 Ms. Srinivasan was unaware, or with respect to any material nonpublic information acquired by her 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) shares issued upon vesting of restricted stock units, which we refer to as RSUs, previously granted to Ms. Srinivasan that vested and were released to Ms. Srinivasan prior to the adoption date, in an amount equal to the lesser of 10,192 shares and such number of shares reasonably estimated such that the gross proceeds from their sale is sufficient to raise $50,000 for purposes of a charitable gift and (ii) up to 6,520 shares issuable upon vesting of RSUs previously granted to Ms. Srinivasan that will vest and be released to Ms. Srinivasan prior to the expiration date.