Robert Paul Bennett - Feb 11, 2022 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role: Chief Executive Officer, Director
Signature: By: /s/ Charles Kallenbach, Attorney-in-Fact for Robert P. Bennett
Stock symbol: ESMT
Transactions as of: Feb 11, 2022
Transactions value $: $830,408
Form type: 4
Date filed: 2/15/2022, 08:40 PM
Previous filing: Mar 29, 2022
Next filing: Apr 5, 2022

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	ESMT	Common Stock	Options Exercise		+2.4K	+0.24%		988K	Jan 1, 2022	Direct	F1
transaction	ESMT	Common Stock	Tax liability	-$20.1K	-833	-0.08%	$24.12	987K	Jan 1, 2022	Direct
transaction	ESMT	Common Stock	Options Exercise	$851K	+150K	+15.22%	$5.67	1.14M	Feb 11, 2022	Direct
holding	ESMT	Common Stock						2.55M	Feb 11, 2022	See footnote	F2

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	-6.25%	$0.00	36.1K	Jan 1, 2022	Common Stock	2.4K		Direct	F1, F3
transaction	ESMT	Stock Option	Options Exercise	$0	+150K	+50%	$0.00	450K	Feb 11, 2022	Common Stock	150K	$5.67	Direct	F4

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

Explanation of Responses:

Id	Content
F1	Each restricted stock unit ("RSU") represents a contingent right to receive one share of common stock.
F2	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.
F3	The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.
F4	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.