Robert Paul Bennett - 01 Oct 2023 Form 4 Insider Report for EngageSmart, Inc.

Role
Chief Executive Officer, Director
Signature
/s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett
Issuer symbol
N/A
Transactions as of
01 Oct 2023
Net transactions value
-$173,801
Form type
4
Filing time
03 Oct 2023, 16:30:16 UTC
Previous filing
14 Jul 2023
Next filing
03 Jan 2024
SEC
View on sec.gov

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +2,404 +0.29% $0.000000 834,984 01 Oct 2023 Direct
transaction ESMT Common Stock Tax liability $19,195 -1,067 -0.13% $17.99 833,917 01 Oct 2023 Direct F1
transaction ESMT Common Stock Options Exercise $0 +19,377 +2.3% $0.000000 853,294 01 Oct 2023 Direct
transaction ESMT Common Stock Tax liability $154,606 -8,594 -1% $17.99 844,700 01 Oct 2023 Direct F1
holding ESMT Common Stock 809,877 01 Oct 2023 The Robert P. Bennett 2020 Grantor Retained Annuity Trust
holding ESMT Common Stock 1,332,000 01 Oct 2023 The Bennett Family 2020 Trust

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Underlying Class Amount Exercise Price Ownership Footnotes
transaction ESMT Restricted Stock Units Options Exercise $0 -2,404 -11% $0.000000 19,231 01 Oct 2023 Common Stock 2,404 Direct F2, F3
transaction ESMT Restricted Stock Units Options Exercise $0 -19,377 -7.1% $0.000000 251,902 01 Oct 2023 Common Stock 19,377 Direct F2, F4
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 Represents the number of shares of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units ("RSUs").
F2 Each RSU represents a contingent right to receive one share of common stock.
F3 The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.
F4 The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.