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

Role: President, Enterprise Solutions Exhibit 24 - Power of Attorney
Signature: By: /s/ Scott Semel, Attorney-in-Fact for Kevin William O'Brien
Issuer symbol: N/A
Transactions as of: 01 Feb 2023
Net transactions value: -$251,494
Form type: 4
Filing time: 03 Feb 2023, 20:48:46 UTC
Previous filing: 03 Feb 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	+42,268		$0.000000	42,268	01 Feb 2023	Direct
transaction	ESMT	Common Stock	Tax liability	$251,494	-12,721	-30%	$19.77	29,547	01 Feb 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 Unit	Options Exercise	$0	-42,268	-25%	$0.000000	126,801	01 Feb 2023	Common Stock	42,268		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 with respect to 25% of the shares on the first anniversary of the date of grant and then in equal installments on each of the 12 quarterly anniversaries thereafter. The RSUs have no expiration date.

Remarks:

President, Enterprise Solutions Exhibit 24 - Power of Attorney