Patrick F. Donovan - 01 Jul 2023 Form 4 Insider Report for EngageSmart, Inc.

Role: Chief Accounting Officer
Signature: /s/ Scott Semel, Attorney-in-Fact for Patrick F. Donovan
Issuer symbol: N/A
Transactions as of: 01 Jul 2023
Net transactions value: -$2,520
Form type: 4
Filing time: 06 Jul 2023, 21:44:55 UTC
Previous filing: 05 Jun 2023
Next filing: 02 Aug 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	+449	+18%	$0.000000	2,978	01 Jul 2023	Direct
transaction	ESMT	Common Stock	Tax liability	$2,520	-132	-4.4%	$19.09	2,846	01 Jul 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	-449	-9.1%	$0.000000	4,488	01 Jul 2023	Common Stock	449		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 April 1, 2022 and have no expiration date.