Kevin William O'Brien - 01 Apr 2023 Form 4 Insider Report for EngageSmart, Inc.

Role: President, Enterprise Solutions
Signature: /s/ Scott Semel, Attorney-in-Fact for Kevin William O'Brien
Issuer symbol: N/A
Transactions as of: 01 Apr 2023
Net transactions value: -$18,056
Form type: 4
Filing time: 04 Apr 2023, 21:43:44 UTC
Previous filing: 07 Feb 2023
Next filing: 03 May 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	+2,113	+7.2%	$0.000000	31,660	01 Apr 2023	Direct
transaction	ESMT	Common Stock	Tax liability	$18,056	-938	-3%	$19.25	30,722	01 Apr 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	-2,113	-6.2%	$0.000000	31,708	01 Apr 2023	Common Stock	2,113		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 shares 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, 2023 and have no expiration date.

Remarks:

President, Enterprise Solutions