FORM 4
☐ Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).         
 UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES
                                                                                  
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940
                      

1. Name and Address of Reporting Person *

HUDSON CASSANDRA		 2. Issuer Name and Ticker or Trading Symbol

EngageSmart, Inc. [ ESMT ] 		5. Relationship of Reporting Person(s) to Issuer (Check all applicable)

_____ Director                    _____ 10% Owner
__X__ Officer (give title below)    _____ Other (specify below)
Chief Financial Officer
(Last)          (First)          (Middle)

C/O ENGAGESMART, INC., 30 BRAINTREE HILL OFFICE PARK, SUITE 101		 3. Date of Earliest Transaction (MM/DD/YYYY)

6/23/2023
(Street)

BRAINTREE, MA 02184		 4. If Amendment, Date Original Filed (MM/DD/YYYY)

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

_X _ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person
(City)        (State)        (Zip)
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. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. 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)
Code V Amount (A) or (D) Price
Common Stock 6/23/2023  M  40000 A$3.46 56923 D  

Table II - Derivative Securities Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3)		2. Conversion or Exercise Price of Derivative Security3. Trans. Date3A. Deemed Execution Date, if any4. Trans. Code
(Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date7. 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 of Derivative Security: Direct (D) or Indirect (I) (Instr. 4)11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Stock Option $3.46 6/23/2023  M     40000   (1)11/1/2030 Common Stock 40000 $0 635000 D  
Explanation of Responses:
(1) The stock option vested and became exercisable with respect to 25% of the shares on November 2, 2021 and vests with respect to the remaining shares in twelve equal quarterly installments beginning on January 1, 2022.

Reporting Owners
Reporting Owner Name / Address
Relationships
Director10% OwnerOfficerOther
HUDSON CASSANDRA
C/O ENGAGESMART, INC.
30 BRAINTREE HILL OFFICE PARK, SUITE 101
BRAINTREE, MA 02184

Chief Financial Officer
Signatures
/s/ Scott Semel, Attorney-in-Fact for Cassandra E. Hudson6/27/2023
**Signature of Reporting PersonDate
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.
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