Jonathan Cole Seltzer - Nov 1, 2022 Form 4 Insider Report for EngageSmart, Inc. (ESMT)

Role: President, SMB Solutions
Signature: By: /s/ Scott Semel, Attorney-in-Fact for Jonathan C. Seltzer
Stock symbol: ESMT
Transactions as of: Nov 1, 2022
Transactions value $: -$140,595
Form type: 4
Date filed: 11/3/2022, 04:05 PM
Previous filing: Oct 12, 2022
Next filing: Jan 4, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	ESMT	Common Stock	Options Exercise	$25.2K	+8.33K	+306.4%	$3.02^*	11.1K	Nov 1, 2022	Direct
transaction	ESMT	Common Stock	Sale	-$166K	-8.33K	-75.39%	$19.89	2.72K	Nov 1, 2022	Direct	F1, 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	Stock Option	Options Exercise	$0	-8.33K	-3.13%	$0.00	258K	Nov 1, 2022	Common Stock	8.33K	$3.02	Direct	F3

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

Explanation of Responses:

Id	Content
F1	The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan.
F2	The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $19.71 to $20.22. The Reporting Person undertakes to provide upon request 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.
F3	The stock option vests and becomes 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.