Robert Paul Bennett - Mar 3, 2023 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role: Chief Executive Officer, Director
Signature: By: /s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett
Stock symbol: ESMT
Transactions as of: Mar 3, 2023
Transactions value $: -$4,826,925
Form type: 4
Date filed: 3/7/2023, 04:54 PM
Previous filing: Feb 7, 2023
Next filing: Apr 4, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	ESMT	Common Stock	Sale	-$4.19M	-230K	-21.22%	$18.19	855K	Mar 3, 2023	Direct	F1
transaction	ESMT	Common Stock	Sale	-$635K	-34.9K	-4.08%	$18.19	820K	Mar 7, 2023	Direct	F1
holding	ESMT	Common Stock						2.35M	Mar 3, 2023	See Footnote	F2

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

Explanation of Responses:

Id	Content
F1	This amount represents a public offering price of $19.00 per share of common stock of EngageSmart, Inc. (the "Common Stock"), less an underwriting discount of $0.8075 per share for shares sold in an underwritten public offering.
F2	Represents (i) 938,978 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) 1,416,000 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.

Content

This amount represents a public offering price of $19.00 per share of common stock of EngageSmart, Inc. (the "Common Stock"), less an underwriting discount of $0.8075 per share for shares sold in an underwritten public offering.

Represents (i) 938,978 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) 1,416,000 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.