X0306 4 2022-04-18 0 0001863105 EngageSmart, Inc. ESMT 0001881898 Seltzer Jonathan Cole C/O ENGAGESMART, INC. 30 BRAINTREE HILL OFFICE PARK, SUITE 101 BRAINTREE MA 02184 0 1 0 0 President, SMB Solutions Common Stock 2022-04-18 4 M 0 8334 3.02 A 9842 D Common Stock 2022-04-18 4 S 0 8334 20.85 D 1508 D Stock Option 3.02 2022-04-18 4 M 0 8334 0.00 D 2029-10-31 Common Stock 8334 291666 D The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan. The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $20.43 to $21.33. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote 2. The stock option vests and becomes exercisable with respect to 25% of the shares on November 1, 2020 and vests with respect to the remaining shares in twelve equal quarterly installments beginning on January 1, 2021. By: /s/ Scott Semel, Attorney-in-Fact for Jonathan C. Seltzer 2022-04-20