X0306 4 2022-07-01 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 Common Stock 2022-07-01 4 M 0 2404 0.00 A 1167922 D Common Stock 2022-07-01 4 F 0 1067 16.40 D 1166855 D Common Stock 2522978 I See footnote Restricted Stock Units 2022-04-01 4 M 0 2404 0.00 D Common Stock 2404 31250 D Includes 27,022 shares of common stock received as annuity payment from The Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee. 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"). Represents (i) 1,022,978 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 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/ Scott Semel, Attorney-in-Fact for Robert P. Bennett 2022-07-06