X0407 4 2023-04-01 0 0001863105 EngageSmart, Inc. ESMT 0001881869 Bennett Robert Paul C/O ENGAGESMART, INC. 30 BRAINTREE HILL OFFICE PARK, SUITE 101 BRAINTREE MA 02184 1 1 0 0 Chief Executive Officer 1 Common Stock 2023-04-01 4 M 0 2403 0.00 A 867942 D Common Stock 2023-04-01 4 F 0 706 19.25 D 867236 D Common Stock 2023-04-01 4 M 0 19377 0.00 A 886613 D Common Stock 2023-04-01 4 F 0 5688 19.25 D 880925 D Common Stock 2023-04-03 4 S 0 14000 18.88 D 866925 D Common Stock 2023-04-03 4 S 0 14000 18.88 D 879877 I The Robert P. Bennett 2020 Grantor Retained Annuity Trust Common Stock 2023-04-03 4 S 0 14000 18.88 D 1402000 I The Bennett Family 2020 Trust Restricted Stock Units 2023-04-01 4 M 0 2403 0.00 D Common Stock 2403 24039 D Restricted Stock Units 2023-04-01 4 M 0 19377 0.00 D Common Stock 19377 290656 D Includes 45,101 shares previously held through the Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee, which were distributed to the Reporting Person on January 31, 2023 and are now owned directly by the Reporting Person. Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units ("RSUs"). The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022. The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.71 to $19.06. The Reporting Person undertakes to provide upon request from 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. The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022. The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.73 to $19.06. The Reporting Person undertakes to provide upon request from 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. The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan dated September 9, 2022. The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.72 to $19.06. The Reporting Person undertakes to provide upon request from 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. Each RSU represents a contingent right to receive one share of common stock. The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date. The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date. /s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett 2023-04-04