X0306 4 2022-05-24 0 0001863105 EngageSmart, Inc. ESMT 0001185573 MANGUM DAVID E C/O ENGAGESMART, INC. 30 BRAINTREE HILL OFFICE PARK, SUITE 101 BRAINTREE MA 02184 1 0 0 0 Restricted Stock Units 2022-05-24 4 A 0 8500 0.00 A Common Stock 8500 8500 D Each restricted stock unit ("RSU") represents a contingent right to receive one share of the Issuer's common stock. The RSUs vest on the earlier of (i) May 24, 2023 and (ii) one day prior to the Company's 2023 annual meeting of shareholders, subject to the Reporting Person's continued service with the Issuer through such vesting date. The RSUs have no expiration date. Exhibit 24 - Power of Attorney. By: /s/ Scott Semel, Attorney-in-Fact for David Mangum 2022-06-29