Sec Form 4 Filing - HUDSON CASSANDRA @ EngageSmart, Inc. - 2024-01-26

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 Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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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/YY) 01/26/2024 (Street) BRAINTREE, MA02184 4. If Amendment, Date Original Filed (MM/DD/YY) 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)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 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) Code V Amount (A) or (D) Price Common Stock 01/26/2024 D 74,326 D $ 23 ( 1 ) 0 D

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 (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 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 (MM/DD/YY) 7. Title and Amount of Underlying Securities (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) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares Restricted Stock Units ( 2 ) 01/26/2024 D 109,796 ( 3 ) ( 3 ) Common Stock 109,796 ( 3 ) 0 D Option to Purchase Common Stock $ 3.46 01/26/2024 D 635,000 ( 4 ) ( 4 ) Common Stock 635,000 ( 4 ) 0 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other HUDSON CASSANDRA C/O ENGAGESMART, INC. 30 BRAINTREE HILL OFFICE PARK, SUITE 101 BRAINTREE, MA02184 Chief Financial Officer Signatures /s/ Scott Semel, Attorney-in-Fact for Cassandra Hudson 01/29/2024 Signature of Reporting Person Date

Explanation of Responses:

( 1 )This Form 4 reports securities disposed of under the Agreement and Plan of Merger (the "Merger Agreement"), dated October 23, 2023, among EngageSmart, Inc. (the "Company"), Icefall Parent, Inc. ("Parent"), and Icefall Merger Sub, LLC ("Merger Sub"), under which Merger Sub was merged with and into the Company (the "Merger"), with the Company continuing as the surviving corporation in the Merger. At the effective time of the Merger (the "Effective Time"), each issued and outstanding share of common stock of the Company ("Shares") was cancelled and converted into the right to receive $23.00 in cash (the "Per Share Price") without interest thereon. ( 2 )Each Company restricted stock unit ("Company RSUs") represented a contingent right to receive one Share upon vesting of the Company RSU. ( 3 )Under the Merger Agreement, at the Effective Time, each Company RSU reported in this Form 4 was cancelled and converted into the contingent right to receive from Parent or the Company a converted cash award (a "Converted Cash Award") with respect to an aggregate amount in cash equal in value to (A) the total number of Shares subject to such Company RSU immediately prior to the Effective Time multiplied by (B) the Per Share Price, which Converted Cash Award will remain subject to the same vesting terms and conditions of the corresponding Company RSU. ( 4 )Under the Merger Agreement, at the Effective Time, each option to purchase Shares (a "Company Option") that was reported in this Form 4 was cancelled and converted into the right to receive an amount (without interest) in cash equal in value to (A) the total number of Shares subject to such Company Option multiplied by (B) the excess, if any, of the Per Share Price over the exercise price per Share underlying such Company Option.

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).

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