CASSANDRA HUDSON - 23 Jun 2023 Form 4 Insider Report for EngageSmart, Inc.

Role: Chief Financial Officer
Signature: /s/ Scott Semel, Attorney-in-Fact for Cassandra E. Hudson
Issuer symbol: N/A
Transactions as of: 23 Jun 2023
Net transactions value: +$138,400
Form type: 4
Filing time: 27 Jun 2023, 16:16:42 UTC
Previous filing: 17 May 2023
Next filing: 06 Jul 2023
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	ESMT	Common Stock	Options Exercise	$138,400	+40,000	+236%	$3.46^*	56,923	23 Jun 2023	Direct

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	-40,000	-5.9%	$0.000000	635,000	23 Jun 2023	Common Stock	40,000	$3.46	Direct	F1

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

Explanation of Responses:

Id	Content
F1	The stock option vested and became exercisable with respect to 25% of the shares on November 2, 2021 and vests with respect to the remaining shares in twelve equal quarterly installments beginning on January 1, 2022.