Robert Paul Bennett - 01 Jan 2024 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 Jan 2024
Net transactions value
-$155,056
Form type
4
Filing time
03 Jan 2024, 20:40:52 UTC
Previous filing
03 Oct 2023
Next filing
29 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 +0.28% $0.000000 847,104 01 Jan 2024 Direct
transaction ESMT Common Stock Tax liability $19,076 -833 -0.1% $22.90 846,271 01 Jan 2024 Direct F1
transaction ESMT Common Stock Options Exercise $0 +19,377 +2.3% $0.000000 865,648 01 Jan 2024 Direct
transaction ESMT Common Stock Tax liability $135,980 -5,938 -0.69% $22.90 859,710 01 Jan 2024 Direct F1
holding ESMT Common Stock 809,877 01 Jan 2024 The Robert P. Bennett 2020 Grantor Retained Annuity Trust
holding ESMT Common Stock 1,332,000 01 Jan 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 -2,404 -13% $0.000000 16,827 01 Jan 2024 Common Stock 2,404 Direct F2, F3
transaction ESMT Restricted Stock Units Options Exercise $0 -19,377 -7.7% $0.000000 232,525 01 Jan 2024 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.