Jonathan Cole Seltzer - 01 Jan 2023 Form 4 Insider Report for EngageSmart, Inc.

Role: President, SMB Solutions
Signature: By: /s/ Scott Semel, Attorney-in-Fact for Jonathan C. Seltzer
Issuer symbol: N/A
Transactions as of: 01 Jan 2023
Net transactions value: -$14,760
Form type: 4
Filing time: 04 Jan 2023, 20:17:36 UTC
Previous filing: 03 Nov 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	+1,202	+44%	$0.000000	3,922	01 Jan 2023	Direct
transaction	ESMT	Common Stock	Tax liability	$8,448	-480	-12%	$17.60	3,442	01 Jan 2023	Direct	F1
transaction	ESMT	Common Stock	Options Exercise	$906	-300	-7.4%	$3.02^*	3,742	03 Jan 2023	Direct
transaction	ESMT	Common Stock	Sale	$5,406	-300	-8%	$18.02	3,442	03 Jan 2023	Direct	F2, F3

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	-1,202	-8.3%	$0.000000	13,221	01 Jan 2023	Common Stock	1,202		Direct	F4, F5
transaction	ESMT	Stock Option	Options Exercise	$0	-300	-0.12%	$0.000000	258,030	03 Jan 2023	Common Stock	300	$3.02	Direct	F6

* 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	The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan.
F3	The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.00 to $18.05. The Reporting Person undertakes to provide upon request the SEC staff, the Issuer, or any shareholder of the Issuer, full information regarding the number of securities sold at each separate price within the range set forth in this footnote.
F4	Each RSU represents a contingent right to receive one share of common stock.
F5	The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.
F6	The stock option vests and becomes exercisable with respect to 25% of the shares on November 1, 2020 and vests with respect to the remaining shares in twelve equal quarterly installments beginning on January 1, 2021.