SEC FORM 4

SEC FORM 4 SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

Bennett Robert Paul

(Last)

(First)

(Middle)

C/O ENGAGESMART, INC.

30 BRAINTREE HILL OFFICE PARK, SUITE 101

(Street)

BRAINTREE

02184

(City)

(State)

(Zip)

2. Issuer Name and Ticker or Trading Symbol
EngageSmart, Inc. [ ESMT ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director	10% Owner
X	Officer (give title below)	Other (specify below)
Chief Executive Officer

3. Date of Earliest Transaction (Month/Day/Year)
07/01/2023

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Rule 10b5-1(c) Transaction Indication

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock	07/01/2023		M		2,404	A	$0	841,329	D
Common Stock	07/01/2023		F⁽¹⁾		706	D	$19.09	840,623	D
Common Stock	07/01/2023		M		19,377	A	$0	860,000	D
Common Stock	07/01/2023		F⁽¹⁾		7,509	D	$19.09	852,491	D
Common Stock	07/03/2023		S⁽²⁾		14,000	D	$18.67⁽³⁾	838,491	D
Common Stock	07/03/2023		S⁽¹⁾		14,000	D	$18.67⁽⁴⁾	837,877	I	The Robert P. Bennett 2020 Grantor Retained Annuity Trust
Common Stock	07/03/2023		S⁽²⁾		14,000	D	$18.67⁽⁵⁾	1,360,000	I	The Bennett Family 2020 Trus

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Restricted Stock Units	⁽⁶⁾	07/01/2023		M			2,404	⁽⁷⁾	⁽⁷⁾	Common Stock	2,404	$0	21,635	D
Restricted Stock Units	⁽⁶⁾	07/01/2023		M			19,377	⁽⁸⁾	⁽⁸⁾	Common Stock	19,377	$0	271,279	D

Explanation of Responses:

1. 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").

2. The sales reported in this Form 4 were effected pursuant to Rule 10b5-1 trading plans, each dated September 9, 2022.

3. The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. The Reporting Person undertakes to provide upon request from 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.

4. The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. The Reporting Person undertakes to provide upon request from 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.

5. The price reported is a weighted average price. The securities were sold in multiple transactions at per share prices ranging from $18.49 to $18.99. The Reporting Person undertakes to provide upon request from 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.

6. Each RSU represents a contingent right to receive one share of common stock.

7. The RSUs vest in 16 equal quarterly installments commencing on January 1, 2022 and have no expiration date.

8. The RSUs vest in 16 equal quarterly installments commencing on April 1, 2023 and have no expiration date.

	/s/ Scott Semel, Attorney-in-Fact for Robert P. Bennett	07/06/2023
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

SEC Form 4 filed by Bennett Robert Paul