X0407 4 2023-04-01 0 0001863105 EngageSmart, Inc. ESMT 0001183112 SEMEL SCOTT N C/O ENGAGESMART, INC. 30 BRAINTREE HILL OFFICE PARK, SUITE 101 BRAINTREE MA 02184 0 1 0 0 Chief Legal Officer 0 Common Stock 2023-04-01 4 M 0 26822 0.00 A 26822 D Common Stock 2023-04-01 4 F 0 7873 19.25 D 18949 D Common Stock 2023-04-01 4 M 0 3523 0.00 A 22472 D Common Stock 2023-04-01 4 F 0 1035 19.25 D 21437 D Restricted Stock Units 2023-04-01 4 M 0 26822 0.00 D Common Stock 26822 80464 D Restricted Stock Units 2023-04-01 4 M 0 3523 0.00 D Common Stock 3523 52846 D 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"). Each RSU represents a contingent right to receive one share of common stock. The RSUs vest with respect to 25% of the shares on April 1, 2023 and then in equal installments on each of the 12 quarterly anniversaries thereafter. The RSUs have no expiration date. The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date. Senior Vice President, General Counsel /s/ Scott Semel 2023-04-04