Jonathan Cole Seltzer - Aug 14, 2023 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role: President, SMB Solutions
Signature: /s/ Scott Semel, Attorney-in-Fact for Jonathan C. Seltzer
Stock symbol: ESMT
Transactions as of: Aug 14, 2023
Transactions value $: -$232,290
Form type: 4
Date filed: 8/15/2023, 05:10 PM
Previous filing: Aug 2, 2023
Next filing: Sep 6, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	ESMT	Common Stock	Options Exercise	$21.8K	+7.22K	+92.85%	$3.02^*	15K	Aug 14, 2023	Direct
transaction	ESMT	Common Stock	Sale	-$254K	-15K	-100%	$16.94	0	Aug 14, 2023	Direct	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	Stock Option	Options Exercise	$0	-7.22K	-3.17%	$0.00	220K	Aug 14, 2023	Common Stock	7.22K	$3.02	Direct	F2

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

Explanation of Responses:

Id	Content
F1	The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $16.89 to $17.01. The Reporting Person undertakes to provide upon request from the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote.
F2	The stock option vested and became exercisable with respect to 25% of the shares on November 1, 2020 and vests with respect to the remaining shares in twelve equal quarterly installments beginning on January 1, 2021.