Sec Form 4 Filing - SUMMIT PARTNERS L P @ EngageSmart, Inc. - 2023-03-03

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

OMB APPROVAL OMB Number: 3235-0287 Expires: November 30, 2011 Estimated average burden hours per response... 0.5

1. Name and Address of Reporting Person SUMMIT PARTNERS L P 2. Issuer Name and Ticker or Trading Symbol EngageSmart, Inc. [ ESMT] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director X __ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) 222 BERKELEY STREET, 18TH FLOOR 3. Date of Earliest Transaction (MM/DD/YY) 03/03/2023 (Street) BOSTON, MA02116 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) _____ Form filed by One Reporting Person __ X __ 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, par value $0.001 per share 03/03/2023 S 1,669,052 ( 1 ) D $ 18.1925 ( 2 ) 25,257,700 ( 3 ) I See Footnote ( 4 ) ( 5 )

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

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other SUMMIT PARTNERS L P 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X Summit Partners Growth Equity Fund VIII-A, L.P. 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X Summit Partners Growth Equity Fund VIII-B, L.P. 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X Summit Partners Entrepreneur Advisors Fund I, L.P. 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X Summit Investors I, LLC 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X Summit Investors I (UK), L.P. 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X SUMMIT MASTER COMPANY, LLC 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X CHUNG PETER Y 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X COLLINS SCOTT C 222 BERKELEY STREET, 18TH FLOOR BOSTON, MA02116 X Signatures /s/ Adam H. Hennessey, as attorney-in-fact for Summit Partners Growth Equity Fund VIII-A, L.P. 03/03/2023 Signature of Reporting Person Date /s/ Adam H. Hennessey, as attorney-in-fact for Summit Partners Growth Equity Fund VIII-B, L.P. 03/03/2023 Signature of Reporting Person Date /s/ Adam H. Hennessey, as attorney-in-fact for Summit Partners Entrepreneur Advisors Fund I, L.P. 03/03/2023 Signature of Reporting Person Date /s/ Adam H. Hennessey, as attorney-in-fact for Summit Investors I, LLC 03/03/2023 Signature of Reporting Person Date /s/ Adam H. Hennessey, as attorney-in-fact for Summit Investors I (UK), L.P. 03/03/2023 Signature of Reporting Person Date /s/ Adam H. Hennessey, as attorney-in-fact for Summit Partners, L.P. 03/03/2023 Signature of Reporting Person Date /s/ Adam H. Hennessey, as attorney-in-fact for Summit Master Company, LLC 03/03/2023 Signature of Reporting Person Date /s/ Adam H. Hennessey, as attorney-in-fact for Peter Y. Chung 03/03/2023 Signature of Reporting Person Date /s/ Adam H. Hennessey, as attorney-in-fact for Scott Collins 03/03/2023 Signature of Reporting Person Date

Explanation of Responses:

( 1 )Represents (i) 1,198,029 shares of Common Stock sold by Summit Partners Growth Equity Fund VIII-A, L.P., (ii) 437,666 shares of Common Stock sold by Summit Partners Growth Equity Fund VIII-B, L.P., (iii) 7,948 shares of Common Stock sold by Summit Partners Entrepreneur Advisors Fund I, L.P., (iv) 22,936 shares of Common Stock sold by Summit Investors I, LLC and (v) 2,473 shares of Common Stock sold by Summit Investors I (UK), L.P. ( 2 )This amount represents a public offering price of $19.00 per share of Common Stock of EngageSmart, Inc. (the "Company"), less an underwriting discount of $0.8075 per share for shares sold in an underwritten public offering. ( 3 )Consists of (i) 18,129,739 shares of Common Stock held by Summit Partners Growth Equity Fund VIII-A, L.P., (ii) 6,623,182 shares of Common Stock held by Summit Partners Growth Equity Fund VIII-B, L.P.,(iii) 120,274 shares of Common Stock held by Summit Partners Entrepreneur Advisors Fund I, L.P., (iv) 347,088 shares of Common Stock held by Summit Investors I, LLC and (v) 37,417 shares of Common Stock held by Summit Investors I (UK), L.P. This amount includes the underwriters' option to purchase up to an additional 252,727 shares of common stock within 30 days of February 28, 2023. ( 4 )Summit Partners, L.P. is the managing member of Summit Partners GE VIII, LLC, which is the general partner of Summit Partners GE VIII, L.P., which is the general partner of each of Summit Partners Growth Equity Fund VIII-A, L.P. and Summit Partners Growth Equity Fund VIII-B, L.P. Summit Master Company, LLC is the (A) sole managing member of Summit Partners Entrepreneur Advisors GP, LLC, which is the general partner of Summit Partners Entrepreneur Advisors Fund I, L.P., and (B) the managing member of Summit Investors Management, LLC, which is the manager of Summit Investors I, LLC and the general partner of Summit Investors I (UK), L.P. Summit Master Company, LLC, as the sole managing member of Summit Partners Entrepreneur Advisors GP, LLC and the managing member of Summit Investors Management, LLC, ( 5 )(Continued from footnote 4), has delegated investment decisions, including voting and dispositive power, to Summit Partners, L.P. Investment decisions for Summit Partners, L.P. are made by its two-person Investment Committee, which is currently composed of Scott Collins and Peter Y. Chung. Summit Partners L.P., Scott Collins and Peter Y. Chung each have voting and dispositive authority over the shares held by each of these entities and therefore beneficially owns such shares. Each of the entities affiliated with Summit Partners, L.P. that are mentioned herein and each of Mr. Collins and Mr. Chung disclaims beneficial ownership of the shares of common stock, in each case, except to the extent of it or his pecuniary interest therein.

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.