Form 3 EngageSmart, Inc. For: Sep 23 Filed by: Osnoss Raphael

September 23, 2021 7:55 PM EDT

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FORM 3 UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

INITIAL STATEMENT OF BENEFICIAL OWNERSHIP OF SECURITIES

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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1. Name and Address of Reporting Person *
Osnoss Raphael

(Last) (First) (Middle)
C/O ENGAGESMART, INC.
30 BRAINTREE HILL OFFICE PARK, SUITE 101

(Street)
BRAINTREE MA 02184

(City) (State) (Zip)
2. Date of Event Requiring Statement (Month/Day/Year)
09/23/2021
3. Issuer Name and Ticker or Trading Symbol
EngageSmart, Inc. [ ESMT ]
4. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
X Director 10% Owner
Officer (give title below) Other (specify below)
5. 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
Table I - Non-Derivative Securities Beneficially Owned
1. Title of Security (Instr. 4) 2. Amount of Securities Beneficially Owned (Instr. 4) 3. Ownership Form: Direct (D) or Indirect (I) (Instr. 5) 4. Nature of Indirect Beneficial Ownership (Instr. 5)
Table II - Derivative Securities Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 4) 2. Date Exercisable and Expiration Date (Month/Day/Year) 3. Title and Amount of Securities Underlying Derivative Security (Instr. 4) 4. Conversion or Exercise Price of Derivative Security 5. Ownership Form: Direct (D) or Indirect (I) (Instr. 5) 6. Nature of Indirect Beneficial Ownership (Instr. 5)
Date Exercisable Expiration Date Title Amount or Number of Shares
Explanation of Responses:
Remarks:
Exhibit 24 - Power of Attorney.
/s/ Charles Kallenbach, Attorney-in-Fact for Raph Osnoss 09/23/2021
** 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.
                                                                      EXHIBIT 24
                                   POWER OF ATTORNEY

        With respect to holdings of and transactions in securities issued by
EngageSmart, Inc. (the "Company"), the undersigned hereby constitutes and
appoints the individuals named on Schedule A attached hereto and as may be
amended from time to time, or any of them signing singly, with full power of
substitution and resubstitution, to act as the undersigned's true and lawful
attorney-in-fact to:

        1.    execute for and on behalf of the undersigned, Schedules 13D and
              13G in accordance with Section 13 of the Securities Exchange Act
              of 1934, as amended (the "Exchange Act"), and the rules
              thereunder, and Forms 3, 4, and 5 in accordance with Section 16
              of the Exchange Act and the rules thereunder;

        2.    do and perform any and all acts for and on behalf of the
              undersigned which may be necessary or desirable to complete and
              execute any such Schedule 13D or 13G or Form 3, 4, or 5, complete
              and execute any amendment or amendments thereto, and timely file
              such schedule or form with the SEC and any stock exchange or
              similar authority; and

        3.    take any other action of any type whatsoever in connection with
              the foregoing which, in the opinion of such attorney-in-fact, may
              be of benefit to, in the best interest of, or legally required by,
              the undersigned, it being understood that the documents executed
              by such attorney-in-fact on behalf of the undersigned pursuant to
              this Power of Attorney shall be in such form and shall contain
              such terms and conditions as such attorney-in-fact may approve in
              such attorney-in-fact's discretion.

        The undersigned hereby grants to each such attorney-in-fact full power
and authority to do and perform any and every act and thing whatsoever
requisite, necessary, or proper to be done in the exercise of any of the rights
and powers herein granted, as fully to all intents and purposes as the
undersigned might or could do if personally present, with full power of
substitution and resubstitution or revocation, hereby ratifying and confirming
all that such attorney-in-fact, or such attorneys-in-fact substitute or
substitutes, shall lawfully do or cause to be done by virtue of this Power of
Attorney and the rights and powers herein granted.

        The undersigned acknowledges that the foregoing attorneys-in-fact, in
serving in such capacity at the request of the undersigned, are not assuming,
nor is the Company assuming, any of the undersigned's responsibilities to comply
with Section 13 and Section 16 of the Exchange Act.

        This Power of Attorney shall remain in full force and effect until the
undersigned is no longer required to file Schedule 13D and 13G and Forms 3, 4,
and 5 with respect to the undersigned's holdings of and transactions in
securities issued by the Company, unless earlier revoked by the undersigned in a
signed writing delivered to the foregoing attorneys-in-fact.

        IN WITNESS WHEREOF, the undersigned has caused this Power of Attorney to
be executed as of this 20th day of September, 2021.


                                        Signature:    /s/ Raph Osnoss
                                                      --------------------------
                                        Print Name:   Raph Osnoss


                                      Schedule A

Robert P. Bennett

Cassandra Hudson

Charles Kallenbach


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