X0306 4 2022-02-11 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 2022-01-01 4 M 0 2403 A 987992 D Common Stock 2022-01-01 4 F 0 833 24.12 D 987159 D Common Stock 2022-02-11 4 M 0 150000 5.67 A 1135589 D Common Stock 2550000 I See footnote Restricted Stock Units 2022-01-01 4 M 0 2403 0.00 D Common Stock 2403 36058 D Stock Option 5.67 2022-02-11 4 M 0 150000 0.00 A 2031-02-01 Common Stock 150000 450000 D Each restricted stock unit ("RSU") represents a contingent right to receive one share of common stock. 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. The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date. The stock option vested and became exercisable with respect to 25% of the underlying shares on February 2, 2022 and will vest with respect to the remaining shares in twelve equal quarterly installments beginning on April 1, 2022, subject to the Reporting Person's continued service to the Issuer through each vesting date. By: /s/ Charles Kallenbach, Attorney-in-Fact for Robert P. Bennett 2022-02-15