144 0001906605 XXXXXXXX LIVE 0001863105 ENGAGESMART, INC. 001-40835 30 BRAINTREE HILL OFFICE PARK SUITE 101 BRAINTREE MA 02184 (781) 848-3733 KEVIN W O'BRIEN Officer Common E*TRADE FINANCIAL CORPORATION

3 EDISON DRIVE ALPHARETTA GA 30005

3000 56504.10 166743782 07/03/2023 NYSE Common 02/01/2023 Restricted Stock Issuer N 3000 02/01/2023 Not Applicable N KEVIN W O'BRIEN

30 BRAINTREE HILL OFFICE PARK SUITE 101 BRAINTREE MA 02184

Common 06/16/2023 9000 164303.10 07/03/2023 03/17/2023 /s/ Kevin William O'Brien