Robert Paul Bennett - 27 Sep 2021 Form 4 Insider Report for EngageSmart, Inc.

Role: Chief Executive Officer, Director
Signature: By: /s/ Charles Kallenbach, Attorney-in-Fact for Robert P. Bennett
Issuer symbol: N/A
Transactions as of: 27 Sep 2021
Net transactions value: -$8,547,728
Form type: 4
Filing time: 29 Sep 2021, 20:10:26 UTC
Previous filing: 23 Sep 2021
Next filing: 29 Mar 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	Sale	$8,547,728	-350,676	-26%	$24.38	985,589	27 Sep 2021	Direct
holding	ESMT	Common Stock						2,550,000	27 Sep 2021	See footnote	F1

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 Unit	Award	$0	+38,461		$0.000000	38,461	27 Sep 2021	Common Stock	38,461		Direct	F2, F3

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

Explanation of Responses:

Id	Content
F1	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.
F2	Each restricted stock unit ("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.