X0306 4 2021-09-27 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 Common Stock 2021-09-27 4 S 0 350676 24.375 D 985589 D Common Stock 2550000 I See footnote Restricted Stock Unit 2021-09-27 4 A 0 38461 0.00 A Common Stock 38461 38461 D Represents (i) 1,050,000 shares of common stock held by The Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee, and (ii) 1,500,000 shares of common stock held by The Bennett Family 2020 Trust, of which John Burgess and Martha Bennett, the Reporting Person's spouse, serve as trustees. John Burgess and Martha Bennett, the Reporting Person's spouse, may be deemed to share voting and dispositive power with respect to the shares held by The Bennett Family 2020 Trust. Each restricted stock unit ("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. By: /s/ Charles Kallenbach, Attorney-in-Fact for Robert P. Bennett 2021-09-29