X0407 4 2023-04-04 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 2023-04-04 4 S 0 14000 18.27 D 852925 D Common Stock 2023-04-04 4 S 0 14000 18.27 D 865877 I The Robert P. Bennett 2020 Grantor Retained Annuity Trust Common Stock 2023-04-04 4 S 0 14000 18.27 D 1388000 I The Bennett Family 2020 Trust Common Stock 2023-04-05 4 S 0 13833 17.24 D 839092 D Common Stock 2023-04-05 4 S 0 167 18.07 D 838925 D Common Stock 2023-04-05 4 S 0 13833 17.24 D 852044 I The Robert P. Bennett 2020 Grantor Retained Annuity Trust Common Stock 2023-04-05 4 S 0 167 18.07 D 851877 I The Robert P. Bennett 2020 Grantor Retained Annuity Trust Common Stock 2023-04-05 4 S 0 13834 17.24 D 1374166 I The Bennett Family 2020 Trust Common Stock 2023-04-05 4 S 0 166 18.07 D 1374000 I The Bennett Family 2020 Trust Each of the sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each 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 $18.05 to $18.84. 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.05 to $18.84. 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.05 to $18.84. 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.88 to $17.83. 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 price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $17.88 to $18.17. 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. /s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett 2023-04-06