Cassandra Hudson - 01 Jan 2023 Form 4 Insider Report for EngageSmart, Inc.

Role: Chief Financial Officer
Signature: By: /s/ Scott Semel, Attorney-in-Fact for Cassandra E. Hudson
Issuer symbol: N/A
Transactions as of: 01 Jan 2023
Net transactions value: -$22,000
Form type: 4
Filing time: 04 Jan 2023, 20:16:42 UTC
Previous filing: 04 Oct 2022
Next filing: 07 Feb 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	$0	+3,605	+33%	$0.000000	14,601	01 Jan 2023	Direct
transaction	ESMT	Common Stock	Tax liability	$22,000	-1,250	-8.6%	$17.60	13,351	01 Jan 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	Restricted Stock Units	Options Exercise	$0	-3,605	-8.3%	$0.000000	39,664	01 Jan 2023	Common Stock	3,605		Direct	F2, F3

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

Explanation of Responses:

Id	Content
F1	Represents the number of common stock withheld to satisfy the tax withholding obligation in connection with the vesting of certain previously reported restricted stock units ("RSUs").
F2	Each 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.