Robert Paul Bennett - Jan 1, 2024 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role
Chief Executive Officer, Director
Signature
/s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett
Stock symbol
ESMT
Transactions as of
Jan 1, 2024
Transactions value $
-$155,056
Form type
4
Date filed
1/3/2024, 08:40 PM
Previous filing
Oct 3, 2023
Next filing
Jan 29, 2024

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction ESMT Common Stock Options Exercise $0 +2.4K +0.28% $0.00 847K Jan 1, 2024 Direct
transaction ESMT Common Stock Tax liability -$19.1K -833 -0.1% $22.90 846K Jan 1, 2024 Direct F1
transaction ESMT Common Stock Options Exercise $0 +19.4K +2.29% $0.00 866K Jan 1, 2024 Direct
transaction ESMT Common Stock Tax liability -$136K -5.94K -0.69% $22.90 860K Jan 1, 2024 Direct F1
holding ESMT Common Stock 810K Jan 1, 2024 The Robert P. Bennett 2020 Grantor Retained Annuity Trust
holding ESMT Common Stock 1.33M Jan 1, 2024 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 -2.4K -12.5% $0.00 16.8K Jan 1, 2024 Common Stock 2.4K Direct F2, F3
transaction ESMT Restricted Stock Units Options Exercise $0 -19.4K -7.69% $0.00 233K Jan 1, 2024 Common Stock 19.4K 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.