Robert Paul Bennett - 01 Jan 2022 Form 4/A - Amendment 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 2022
Net transactions value: +$830,408
Form type: 4/A - Amendment
Filing time: 29 Mar 2022, 18:58:49 UTC
Date Of Original Report: 15 Feb 2022
Previous filing: 29 Sep 2021
Next filing: 15 Feb 2022
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		+2,403	+0.24%		987,992	01 Jan 2022	Direct	F1, F2
transaction	ESMT	Common Stock	Tax liability	$20,092	-833	-0.08%	$24.12	987,159	01 Jan 2022	Direct
transaction	ESMT	Common Stock	Options Exercise	$850,500	+150,000	+15%	$5.67	1,137,159	11 Feb 2022	Direct	F3
holding	ESMT	Common Stock						2,550,000	01 Jan 2022	See footnote	F4

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	-2,403	-6.2%	$0.000000	36,058	01 Jan 2022	Common Stock	2,403		Direct	F2, F5
transaction	ESMT	Stock Option	Options Exercise	$0	+150,000	+50%	$0.000000	450,000	11 Feb 2022	Common Stock	150,000	$5.67	Direct	F6

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	On February 15, 2022, the Reporting Person filed a Form 4 (the "Original Form 4") which inadvertently indicated that the date of earliest transaction required to be reported was 02/11/2022. The correct date of earliest transaction required to be reported is 01/01/2022. This amendment is being filed to correct the date of the earliest transaction required to be reported.
F2	Each restricted stock unit ("RSU") represents a contingent right to receive one share of common stock.
F3	The Original Form 4 inadvertently incorrectly stated the total number of shares of common stock directly beneficially owned by the Reporting Person. This amendment is being filed to correct the total number of shares of common stock directly beneficially owned by the Reporting Person.
F4	Represents (i) 1,050,000 shares of common stock held by The Robert P. Bennett 2020 Grantor Retained Annuity Trust, of which the Reporting Person serves as the sole trustee, and (ii) 1,500,000 shares of common stock held by The Bennett Family 2020 Trust, of which John Burgess and Martha Bennett, the Reporting Person's spouse, serve as trustees. John Burgess and Martha Bennett, the Reporting Person's spouse, may be deemed to share voting and dispositive power with respect to the shares held by The Bennett Family 2020 Trust.
F5	The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.
F6	The stock option vested and became exercisable with respect to 25% of the underlying shares on February 2, 2022 and will vest with respect to the remaining shares in twelve equal quarterly installments beginning on April 1, 2022, subject to the Reporting Person's continued service to the Issuer through each vesting date.

Remarks:

Exhibit 24 - Power of Attorney.