Document:

EX-4.3

 Exhibit 4.3 
  

 
 ENGAGESMART 
.
ZQ|CERT#|COY|CLS|RGSTRY|ACCT#|TRANSTYPE|RUN#|TRANS# 
COMMON STOCK COMMON STOCK

PAR VALUE $0.001 
Certificate Shares 
Number * * 000000 ****************** 
* * * 000000 ***************** 
ZQ00000000 
**** 000000 **************** 
ENGAGESMART, INC. ***** 000000 *************** ****** 000000 ************** 
INCORPORATED UNDER
THE LAWS OF THE STATE OF DELAWARE 
** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample ****
Mr. Alexander David Sample **** Mr. Alexander David Sample SEE REVERSE FOR CERTAIN DEFINITIONS 
**** Mr. Alexander David Sample ****
Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David THIS CERTIFIES THAT Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample ****
Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. MR. Alexander David SAMPLE Sample **** Mr. Alexander David &Sample MRS. **** Mr. Alexander SAMPLE David Sample
**** Mr. Alexander & David    Sample **** Mr. 
Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander
David Sample **** Mr Alexander David Sample **** Mr. Alexander David Sample **** CUSIP XXXXXX XX X Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample
**** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander MR.
David Sample SAMPLE **** Mr. Alexander David Sample **** &Mr. Alexander MRS. David Sample SAMPLE **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander
David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. 
Alexander David Sample **** Mr. Alexander David Sample ****
Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David Sample **** Mr. Alexander David
Sample **** Mr. Sample **** Mr. Sample 
is the owner of
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****000000**Shares****000000**Shares***
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****000000**Shares****000000**Shares**** 
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****000000**Shares****000000**Shares****0 THIS CERTIFICATE IS TRANSFERABLE IN
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****000000**Shares****000000**Shares****00 ***ZERO HUNDRED
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****000000**Shares****000000**Shares****000 CITIES DESIGNATED BY THE TRANSFER 000**Shares****000000**Shares****000000**Shares****000000**Shares****000000**Shares****000000**Shares

****000000**Shares****000000**Shares****0000 AGENT, AVAILABLE ONLINE AT
00**Shares****000000**Shares****000000**Shares****000000**Shares****000000**Shares****000000**Shares 
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****000000**Shares****000000**Shares****000000**S 
FULLY-PAID AND NON-ASSESSABLE SHARES OF COMMON STOCK OF 
EngageSmart, Inc. (hereinafter called the “Company”), transferable on the
books of the Company in person or by duly authorized attorney, upon surrender of this Certificate properly endorsed. This Certificate and the shares represented hereby, are issued and shall be held subject to all of the provisions of the Certificate
of Incorporation, as amended, and the By-Laws, as amended, of the Company (copies of which are on file with the Company and with the Transfer Agent), to all of which each holder, by acceptance hereof, assents.
This Certificate is not valid unless countersigned and registered by the Transfer Agent and Registrar. 
Witness the facsimile seal of the Company and the facsimile
signatures of its duly authorized officers. 
DATED DD-MMM-YYYY 
ESMA 
FACSIMILE SIGNATURE TO COME G RT COUNTERSIGNED AND REGISTERED: 
A , 
POR I

G R A COMPUTERSHARE TRUST COMPANY, N.A. 
CO TE N 
E N C 
President . TRANSFER AGENT AND REGISTRAR, 
9/21/2021 
DEL RE 
FACSIMILE SIGNATURE TO COME AWA 
By 
Secretary AUTHORIZED SIGNATURE 
CUSIP/IDENTIFIER XXXXXX XX X 
Holder ID XXXXXXXXXX 
Insurance Value 00.1,000,000 Number of Shares 123456 
DTC 12345678901234512345678     
PO BOX 505006, Louisville, KY 40233-5006

Certificate Numbers Num/No Denom. Total. 
MR A SAMPLE 1234567890/1234567890
111 DESIGNATION (IF ANY) 1234567890/1234567890 222 
ADD 1 
ADD 2
1234567890/1234567890 333 1234567890/1234567890 444 
ADD 3 
ADD 4
1234567890/1234567890 555 1234567890/1234567890 666 
Total Transaction 7 

 

 
 ENGAGESMART, INC. 
THE COMPANY WILL FURNISH WITHOUT
CHARGE TO EACH SHAREHOLDER WHO SO REQUESTS, A SUMMARY OF THE POWERS, DESIGNATIONS, PREFERENCES AND RELATIVE, PARTICIPATING, OPTIONAL OR OTHER SPECIAL RIGHTS OF EACH CLASS OF STOCK OF THE COMPANY AND THE QUALIFICATIONS, LIMITATIONS OR RESTRICTIONS OF
SUCH PREFERENCES AND RIGHTS, AND THE VARIATIONS IN RIGHTS, PREFERENCES AND LIMITATIONS DETERMINED FOR EACH SERIES, WHICH ARE FIXED BY THE CERTIFICATE OF INCORPORATION OF THE COMPANY, AS AMENDED, AND THE RESOLUTIONS OF THE BOARD OF DIRECTORS OF THE
COMPANY, AND THE AUTHORITY OF THE BOARD OF DIRECTORS TO DETERMINE VARIATIONS FOR FUTURE SERIES. SUCH REQUEST MAY BE MADE TO THE OFFICE OF THE SECRETARY OF THE COMPANY OR TO THE TRANSFER AGENT. THE BOARD OF DIRECTORS MAY REQUIRE THE OWNER OF A LOST
OR DESTROYED STOCK CERTIFICATE, OR HIS LEGAL REPRESENTATIVES, TO GIVE THE COMPANY A BOND TO INDEMNIFY IT AND ITS TRANSFER AGENTS AND REGISTRARS AGAINST ANY CLAIM THAT MAY BE MADE AGAINST THEM ON ACCOUNT OF THE ALLEGED LOSS OR DESTRUCTION OF ANY SUCH
CERTIFICATE. 
The following abbreviations, when used in the inscription on the face of this certificate, shall be construed as though they were written out in full
according to applicable laws or regulations: 
TEN COM—as tenants in
common                UNIF GIFT MIN ACT -............................................Custodian 
(Cust)                (Minor) 
TEN ENT - as tenants by the entireties                under Uniform Gifts to Minors Act 
(State) 
JT TEN    —as joint tenants with right of
survivorship                UNIFTRF MIN ACT    -............................................Custodian (until age ................................)

and not as tenants in common                (Cust) 
.............................under Uniform Transfers to Minors
Act                (Minor)                (State) 
Additional abbreviations may also be used though not in the above list. 
PLEASE INSERT SOCIAL
SECURITY OR OTHER IDENTIFYING NUMBER OF ASSIGNEE 
For value received, ____________________________hereby sell, assign and transfer unto 
(PLEASE PRINT OR TYPEWRITE NAME AND ADDRESS, INCLUDING POSTAL ZIP CODE, OF ASSIGNEE) 
Shares of
the common stock represented by the within Certificate, and do hereby irrevocably constitute and appoint Attorney to transfer the said stock on the books of the within-named Company with full power of substitution in the premises. 
Dated: __________________________________________20__________________ Signature(s) Guaranteed: Medallion Guarantee Stamp 
THE SIGNATURE(S) SHOULD BE GUARANTEED BY AN ELIGIBLE GUARANTOR INSTITUTION (Banks, Stockbrokers, Savings and Loan Associations and Credit Unions) WITH MEMBERSHIP IN AN APPROVED
SIGNATURE GUARANTEE MEDALLION PROGRAM, PURSUANT TO S.E.C. RULE 17Ad-15. 
Signature:
____________________________________________________________ 
Signature:
____________________________________________________________                Notice: The signature to this assignment must correspond with the name as written upon the
face of the certificate, in every particular, without alteration or enlargement, or any change whatever. 
The IRS requires that the named transfer agent
(“we”) report the cost basis of certain shares or units acquired after January 1, 2011. If your shares or units are covered by the legislation, and you requested to sell or transfer the shares or units using a specific cost basis
calculation method, then we have processed as you requested. If you did not specify a cost basis calculation method, then we have defaulted to the first in, first out (FIFO) method. Please consult your tax advisor if you need additional information
about cost basis. 
If you do not keep in contact with the issuer or do not have any activity in your account for the time period specified by state law, your
property may become subject to state unclaimed property laws and transferred to the appropriate state.EX-10.11

 Exhibit 10.11 

EMPLOYMENT AGREEMENT 

THIS EMPLOYMENT AGREEMENT (this “Agreement”) is entered into by and between EngageSmart, LLC (the
“Company”) and Robert Bennett (the “Executive”). 
 WHEREAS, the Executive is currently
employed as Chief Executive Officer of the Company; 
 WHEREAS, the Company is contemplating an initial public offering (the
“IPO”); 
 WHEREAS, in connection with the IPO, the Company will convert into EngageSmart, Inc., a Delaware
corporation (the “Corporate Conversion”); 
 WHEREAS, in connection with the IPO and Corporate Conversion, the
Company desires to assure itself of the continued services of the Executive by engaging the Executive to perform services under the terms hereof; 

WHEREAS, the Executive desires to provide services to the Company on the terms herein provided; and 

WHEREAS, the Company and the Executive desire to have the Agreement become effective as of the date of the consummation of the Corporate
Conversion (the “Effective Date”). 
 NOW, THEREFORE, IT IS HEREBY AGREED AS FOLLOWS: 

1. Employment Period. Subject to the provisions for earlier termination hereinafter provided, the Executive’s employment hereunder
shall be for a term commencing on the Effective Date and ending on the second anniversary of the Effective Date (the “Initial Term”). The Initial Term shall automatically be extended for successive one year periods (each an
“Extension Term” and, collectively with the Initial Term, the “Employment Period”) unless either party hereto gives notice of non-extension of the Employment
Period to the other no later than ninety (90) days prior to the expiration of the then-applicable Initial Term or Extention Term. The Executive’s employment hereunder is terminable at will by the Company or by the Executive at any time
(for any reason or for no reason), subject to the provisions of Section 4 hereof. For purposes of this Agreement and for the avoidance of doubt, notice by the Company of non-extension of the Employment
Period shall not constitute a termination without Cause or Good Reason for the Executive to terminate his or her employment. Notwithstanding anything in this agreement to the contratry, if the Corporate Conversion and the IPO are not consummated for
any reason, this Agreement shall be null and void ab initio and neither the Executive nor the Company shall have any rights or obligations hereunder. 

2. Terms of Employment. 

(a) Position and Duties. 

(i) Role and Responsibilities. During the Employment Period, the Executive shall serve as Chief Executive Officer of the
Company, and shall perform such employment duties as are usual and customary for such position. The Executive shall report directly to the Board of Directors of the Company. At the Company’s request, the Executive shall serve the Company and/or
its subsidiaries and affiliates in other capacities in addition to the foregoing, consistent with the Executive’s position. In the event that the Executive, during the Employment Period, serves in any one or more of such additional capacities,
the Executive’s compensation shall not be increased beyond that specified in Section 2(b) hereof. In addition, in the event the Executive’s service in one or more of such additional capacities is terminated, the Executive’s
compensation, as specified in Section 2(b) hereof, shall not be diminished or reduced in any manner as a result of such termination provided that the Executive otherwise remains employed under the terms of this Agreement. 

 (ii) Exclusivity. During the Employment Period, and excluding any
periods of vacation and sick leave to which the Executive may be entitled, the Executive agrees to devote his or her full business time and attention to the business and affairs of the Company. Notwithstanding the foregoing, during the Employment
Period, it shall not be a violation of this Agreement for the Executive to: (A) serve on boards, committees or similar bodies of charitable or nonprofit organizations, and up to two (2) boards or committees of for-profit companies, (B) fulfill limited teaching, speaking and writing engagements, and (C) manage his or her personal investments, in each case, so long as such activities do not individually or in the
aggregate materially interfere or conflict with the performance of the Executive’s duties and responsibilities under this Agreement; provided, that with respect to the activities in subclauses (A) and/or (B), the Executive receives
prior written approval from the Chief Executive Officer. 
 (iii) Principal Location. During the Employment Period,
the Executive shall perform the services required by this Agreement at the Company’s principal offices located in Braintree, Massachusetts (the “Principal Location”), except for travel to other locations as may be
necessary to fulfill the Executive’s duties and responsibilities hereunder. 
 (b) Compensation, Benefits, Etc. 

(i) Base Salary. During the Employment Period, the Executive shall receive a base salary (the “Base
Salary”) of $600,000 per annum. The Base Salary shall be reviewed annually by the Compensation Committee (the “Compensation Committee”) of the Board of Directors of the Company (the
“Board”) and may be increased from time to time by the Compensation Committee in its sole discretion. The Base Salary shall be paid in accordance with the Company’s normal payroll practices for executive salaries
generally, but no less often than monthly. The Base Salary may be increased in the Compensation Committee’s discretion, but not reduced, and the term “Base Salary” as utilized in this Agreement shall refer to the Base Salary as so
increased. 
 (ii) Annual Cash Bonus. In addition to the Base Salary, the Executive shall be eligible to earn, for
each fiscal year of the Company ending during the Employment Period, a discretionary cash performance bonus (an “Annual Bonus”) under the Company’s bonus plan or program applicable to senior executives. The
Executive’s target Annual Bonus shall be at least forty percent (40%) of the Base Salary actually paid for such year (the “Target Bonus”). The actual amount of any Annual Bonus shall be determined by reference to the
attainment of Company performance metrics and/or individual performance objectives, in each case, as determined by the Compensation Committee, and may be greater or less than the Target Bonus (or zero). Subject to Section 4(a)(i) hereof,
payment of any Annual Bonus(es), to the extent any Annual Bonus(es) become payable, will be contingent upon the Executive’s continued employment through the applicable payment date, which shall occur on the date on which annual bonuses are paid
generally to the Company’s senior executives. 

  
 2 

 (iii) Benefits. During the Employment Period, the Executive (and the
Executive’s spouse and/or eligible dependents to the extent provided in the applicable plans and programs) shall be eligible to participate in and be covered under the health and welfare benefit plans and programs maintained by the Company for
the benefit of its senior executive employees from time to time, pursuant to the terms of such plans and programs including any medical, life, hospitalization, dental, disability, accidental death and dismemberment and travel accident insurance
plans and programs. During the Employment Period, the Company shall provide the Executive and the Executive’s eligible dependents with coverage under its group health plans. In addition, during the Employment Period, Executive shall be eligible
to participate in any retirement, savings and other employee benefit plans and programs maintained from time to time by the Company for the benefit of its senior executive officers. Nothing contained in this Section 2(b)(iii) shall create or be
deemed to create any obligation on the part of the Company to adopt or maintain any health, welfare, retirement or other benefit plan or program at any time or to create any limitation on the Company’s ability to modify or terminate any such
plan or program. 
 (iv) Expenses. During the Employment Period, the Executive shall be entitled to receive prompt
reimbursement for all reasonable business expenses incurred by the Executive in accordance with the policies, practices and procedures of the Company provided to senior executive employees of the Company. 

(v) Fringe Benefits. During the Employment Period, the Executive shall be eligible to receive such fringe benefits and
perquisites as are provided by the Company to its senior executive employees from time to time, in accordance with the policies, practices and procedures of the Company, and shall receive such additional fringe benefits and perquisites as the
Company may, in its discretion, from time-to-time provide. 

(vi) Vacation. During the Employment Period, the Executive shall be entitled to paid vacation in accordance with the
plans, policies, programs and practices of the Company applicable to its senior executives. 
 3. Termination of Employment. 

(a) Death or Disability. The Executive’s employment shall terminate automatically upon the Executive’s death during the
Employment Period. Either the Company or the Executive may terminate the Executive’s employment in the event of the Executive’s Disability during the Employment Period. For purposes of this Agreement, “Disability”
shall mean that the Executive has become entitled to receive benefits under an applicable Company long-term disability plan or, if no such plan covers the Executive, as determined in the reasonable discretion of the Board. 

(b) Termination by the Company. The Company may terminate the Executive’s employment during the Employment Period for Cause or
without Cause. For purposes of this Agreement, “Cause” shall have the meaning provided in the Company’s 2021 Incentive Award Plan. 

(c) Termination by the Executive. The Executive’s employment may be terminated by the Executive for any reason, including with Good
Reason or by the Executive without Good Reason. For purposes of this Agreement, “Good Reason” shall mean the occurrence of any one or more of the following events without the Executive’s prior written consent, unless the
Company fully corrects the circumstances constituting Good Reason (provided such circumstances are capable of correction) as provided below: 

(i) a material diminution in the Executive’s position (including status, offices, titles and reporting hierarchy or
requirements), authority, duties or responsibilities as contemplated by Section 2(a) hereof, excluding for this purpose any isolated, insubstantial or inadvertent actions not taken in bad faith and which are remedied by the Company promptly
after receipt of notice thereof given by the Executive; 

  
 3 

 (ii) the Company’s material reduction of the Executive’s Base
Salary, as the same may be increased from time to time; 
 (iii) a material change in the geographic location of the
Principal Location which shall, in any event, include only a relocation of the Principal Location by more than twenty-five (25) miles from its existing location; 

(iv) the Company’s material breach of this Agreement. 

Notwithstanding the foregoing, the Executive will not be deemed to have resigned for Good Reason unless (1) the Executive provides the Company with
written notice setting forth in reasonable detail the facts and circumstances claimed by the Executive to constitute Good Reason within sixty (60) days after the date of the occurrence of any event that the Executive knows or should reasonably
have known to constitute Good Reason, (2) the Company fails to cure such acts or omissions within thirty (30) days following its receipt of such notice, and (3) the effective date of the Executive’s termination for Good Reason
occurs no later than sixty (60) days after the expiration of the Company’s cure period. 
 (d) Notice of Termination. Any
termination by the Company for Cause, or by the Executive for Good Reason, shall be communicated by a Notice of Termination to the other parties hereto given in accordance with Section 10(b) hereof. For purposes of this Agreement, a
“Notice of Termination” means a written notice which (i) indicates the specific termination provision in this Agreement relied upon, (ii) sets forth in reasonable detail the facts and circumstances claimed to
provide a basis for termination of the Executive’s employment under the provision so indicated and (iii) if the Date of Termination (as defined below) is other than the date of receipt of such notice, specifies the termination date (which
date shall be not more than thirty (30) days after the giving of such notice). The failure by the Executive or the Company to set forth in the Notice of Termination any fact or circumstance which contributes to a showing of Good Reason or Cause
shall not waive any right of the Executive or the Company, respectively, hereunder or preclude the Executive or the Company, respectively, from asserting such fact or circumstance in enforcing the Executive’s or the Company’s rights
hereunder. 
 (e) Termination of Offices and Directorships; Return of Property. Upon termination of the Executive’s employment
for any reason, unless otherwise specified in a written agreement between the Executive and the Company, the Executive shall be deemed to have resigned from all offices, directorships, and other employment positions if any, then held with the
Company, and shall take all actions reasonably requested by the Company to effectuate the foregoing. In addition, upon the termination of the Executive’s employment for any reason, the Executive agrees to return to the Company all documents of
the Company and its affiliates (and all copies thereof) and all other Company or Company affiliate property that the Executive has in his or her possession, custody or control. Such property includes, without limitation: (i) any materials of
any kind that the Executive knows contain or embody any proprietary or confidential information of the Company or an affiliate of the Company (and all reproductions thereof), (ii) computers (including, but not limited to, laptop computers, desktop
computers and similar devices) and other portable electronic devices (including, but not limited to, tablet computers), cellular phones/smartphones, credit cards, phone cards, entry cards, identification badges and keys, and (iii) any
correspondence, drawings, manuals, letters, notes, notebooks, reports, programs, plans, proposals, financial documents, or any other documents concerning the customers, business plans, marketing strategies, products and/or processes of the Company
or any of its affiliates and any information received from the Company or any of its affiliates regarding third parties. 

  
 4 

 4. Obligations of the Company upon Termination. Upon a termination of the
Executive’s employment for any reason, the Executive shall be paid, in a single lump-sum payment on the date of the Executive’s termination of employment, the aggregate amount of the Executive’s
(i) earned but unpaid Base Salary, (ii) accrued but unpaid vacation pay through the date of such termination, and (iii) any reasonable business expenses incurred by the Executive prior to the date of such termination and reimbursable
under Section 2(b)(iv), above (the “Accrued Obligations”). 
 (a) Without Cause or For Good Reason. If
the Executive’s employment with the Company is terminated during the Employment Period (x) by the Company without Cause (other than by reason of the Executive’s Disability or due to the expiration of the Employment Period) or
(y) by the Executive for Good Reason (in either case, a “Qualifying Termination”), then following the Executive’s Separation from Service (as defined below) (such date, the “Date of
Termination”), in each case, subject to and conditioned upon compliance with Section 4(d) hereof, in addition to the Accrued Obligations: 

(i) Cash Severance. The Company shall continue to pay to the Executive the Executive’s Base Salary in effect on the
Date of Termination during the period beginning on the Date of Termination and ending on the 12-month anniversary of the Date of Termination in instalments in accordance with the Company’s regular payroll practices as of the Date of
Termination; provided that, notwithstanding the foregoing, if such Qualifying Termination occurs within the period beginning 3 months prior to a Change in Control, as defined in the Company’s 2021 Incentive Award Plan, as amended (and such
Change in Control constitutes a “change in control event” as defined in Treasury Regulations Section 1.409A-3(i)(5)) and ending 12 months following such Change in Control (a “Change
in Control Termination”), then in lieu of the foregoing payments set forth in this Section 4(a)(i), the Company shall pay to the Executive (A) a single lump-sum amount equal to 18 months
of Executive’s Base Salary in effect on the Date of Termination on the sixtieth (60th) day after the Date of Termination, (B) a pro-rata Annual
Bonus to which the Executive would have become entitled (if any) for the fiscal year of the Company during which the Date of Termination occurs, had the Executive remained employed through the payment date and paid at target, pro-rated based on the number of days during such fiscal year that the Executive was employed by the Company and payable in a single lump-sum payment on the date on which
annual bonuses are paid to the Company’s senior executives generally for such year, but in no event later than March 15th of the calendar year immediately following the calendar year in which
the Date of Termination occurs, with the actual date within such period determined by the Company in its sole discretion, and (C) notwithstanding anything to the contrary in any Company equity plan or any award agreement issued under any
Company equity plan, full vesting acceleration of any Company equity awards that vest solely based on the passage of time and that are held by the Executive as of the Date of Termination.. 

(ii) COBRA. During the period commencing on the Date of Termination and ending on the
6-month anniversary of the Date of Termination (or, in the event of a Change in Control Termination, the 18-month anniversary of the Date of Termination) (as applicable,
the “COBRA Period”), subject to the Executive’s valid election to continue healthcare coverage under Section 4980B of the Internal Revenue Code and the regulations thereunder (together, the
“Code”), the Company shall continue to provide the Executive and the Executive’s eligible dependents with coverage under its group health plans at the same levels and the same cost to the Executive as would have applied
if the Executive’s employment had not been terminated based on the Executive’s elections in effect on the Date of Termination, provided, however, that (A) if any plan pursuant to which such benefits are provided
is not, or ceases prior to the expiration of the period of continuation coverage to be, exempt from the application of Section 409A (as defined below) under Treasury Regulation
Section 1.409A-1(a)(5), or (B) the Company is otherwise unable to continue to cover the Executive under its group health plans without incurring penalties (including without limitation, pursuant to
Section 2716 of the Public Health Service Act or the Patient Protection and Affordable Care Act), then, in either case, an amount equal to each remaining Company subsidy shall thereafter be paid to the Executive in substantially equal monthly
installments over the continuation coverage period (or the remaining portion thereof). 

  
 5 

 Notwithstanding the foregoing, it shall be a condition to the Executive’s right to receive the amounts
provided for in Sections 4(a)(i) and 4(a)(ii) hereof that the Executive execute and deliver to the Company an effective release of claims in substantially the form attached hereto as Exhibit A (the “Release”) within twenty-one (21) days (or, to the extent required by law, forty-five (45) days) following the Date of Termination and that the Executive not revoke such Release during any applicable revocation period. 

(b) Death or Disability. Subject to Section 4(d) hereof, if the Executive incurs a Separation from Service by reason of the
Executive’s death or Disability during the Employment Period, then in addition to the Accrued Obligations, all outstanding equity awards that vest based solely on the passage of time that are held by the Executive on the Date of Termination
shall immediately become fully vested and, as applicable, exercisable. 
 (c) For Cause, Without Good Reason or Other Terminations. If
the Company terminates the Executive’s employment for Cause, the Executive terminates the Executive’s employment without Good Reason, or the Executive’s employment terminates for any other reason not enumerated in Sections 4(a) or
4(b) hereof, in any case, during the Employment Period, or if the Executive’s employment with the Company is terminated due to the expiration of the Employment Period, then, in any case, the Company shall pay to the Executive the Accrued
Obligations in cash within thirty (30) days after the Date of Termination (or by such earlier date as may be required by applicable law), and the Executive shall have no further rights hereunder. 

(d) Six-Month Delay. Notwithstanding anything to the contrary in this Agreement, no compensation
or benefits, including without limitation any severance payments or benefits payable under Section 4 hereof, shall be paid to the Executive during the six (6)-month period following the Executive’s “separation from service” from
the Company (within the meaning of Section 409A, a “Separation from Service”) if the Company determines that paying such amounts at the time or times indicated in this Agreement would be a prohibited distribution under
Section 409A(a)(2)(B)(i) of the Code. If the payment of any such amounts is delayed as a result of the previous sentence, then on the first day of the seventh month following the date of Separation from Service (or such earlier date upon which
such amount can be paid under Section 409A without resulting in a prohibited distribution, including as a result of the Executive’s death), the Company shall pay the Executive a lump-sum amount equal
to the cumulative amount that would have otherwise been payable to the Executive during such period. 
 (e) Exclusive Benefits. Except
as expressly provided in this Section 4 and subject to Section 5 hereof, the Executive shall not be entitled to any additional payments or benefits upon or in connection with the Executive’s termination of employment. 

5. Non-Exclusivity of Rights. Amounts which are vested benefits or which the Executive is
otherwise entitled to receive under any plan, policy, practice or program of or any contract or agreement with the Company at or subsequent to the Date of Termination shall be payable in accordance with such plan, policy, practice or program or
contract or agreement except as explicitly modified by this Agreement. 

  
 6 

 6. Excess Parachute Payments, Limitation on Payments. 

(a) Best Pay Cap. Notwithstanding any other provision of this Agreement, in the event that any payment or benefit received or to be
received by the Executive (including any payment or benefit received in connection with a termination of the Executive’s employment, whether pursuant to the terms of this Agreement or any other plan, arrangement or agreement) (all such payments
and benefits, including the payments and benefits under Section 4 hereof, being hereinafter referred to as the “Total Payments”) would be subject (in whole or part), to the excise tax imposed under Section 4999 of
the Code (the “Excise Tax”), then, after taking into account any reduction in the Total Payments provided by reason of Section 280G of the Code in such other plan, arrangement or agreement, the cash severance payments
under this Agreement shall first be reduced, and the noncash severance payments hereunder shall thereafter be reduced, to the extent necessary so that no portion of the Total Payments is subject to the Excise Tax but only if (i) the net amount
of such Total Payments, as so reduced (and after subtracting the net amount of federal, state and local income taxes on such reduced Total Payments and after taking into account the phase out of itemized deductions and personal exemptions
attributable to such reduced Total Payments) is greater than or equal to (ii) the net amount of such Total Payments without such reduction (but after subtracting the net amount of federal, state and local income taxes on such Total Payments and
the amount of Excise Tax to which the Executive would be subject in respect of such unreduced Total Payments and after taking into account the phase out of itemized deductions and personal exemptions attributable to such unreduced Total Payments).

 (b) Certain Exclusions. For purposes of determining whether and the extent to which the Total Payments will be subject to the
Excise Tax, (i) no portion of the Total Payments the receipt or enjoyment of which the Executive shall have waived at such time and in such manner as not to constitute a “payment” within the meaning of Section 280G(b) of the Code
shall be taken into account; (ii) no portion of the Total Payments shall be taken into account which, in the written opinion of an independent, nationally recognized accounting or consulting firm (the “Independent
Advisors”) selected by the Company, does not constitute a “parachute payment” within the meaning of Section 280G(b)(2) of the Code (including by reason of Section 280G(b)(4)(A) of the Code) and, in calculating the
Excise Tax, no portion of such Total Payments shall be taken into account which, in the opinion of the Independent Advisors, constitutes reasonable compensation for services actually rendered, within the meaning of Section 280G(b)(4)(B) of the
Code, in excess of the “base amount” (as defined in Section 280G(b)(3) of the Code) allocable to such reasonable compensation; and (iii) the value of any non-cash benefit or any deferred
payment or benefit included in the Total Payments shall be determined by the Independent Advisors in accordance with the principles of Sections 280G(d)(3) and (4) of the Code. 

7. Confidential Information, Non-Competition and
Non-Solicitation. 
 (a) The Executive shall hold in a fiduciary capacity for the benefit of the
Company all secret or confidential information, knowledge or data relating to the Company and its subsidiaries and affiliates, which shall have been obtained by the Executive in connection with the Executive’s employment by the Company and
which shall not be or become public knowledge (other than by acts by the Executive or representatives of the Executive in violation of this Agreement). After termination of the Executive’s employment with the Company, the Executive shall not,
without the prior written consent of the Company or as may otherwise be required by law or legal process, communicate or divulge any such information, knowledge or data, to anyone other than the Company and those designated by it; provided,
however, that if the Executive receives actual notice that the Executive is or may be required by law or legal process to communicate or divulge any such information, knowledge or data, the Executive shall promptly so notify the Company. 

(b) While employed by the Company and, for a period of twelve (12) months after the Date of Termination, the Executive shall not, at any
time, directly or indirectly engage in, have any interest in (including, without limitation, through the investment of capital or lending of money or property), or manage, operate or otherwise render any services to, any person or entity (whether on
his or her own or in association with others, as a principal, director, officer, employee, agent, representative, partner, member, security holder, consultant, advisor, independent contractor, owner, investor, participant or in any other

  
 7 

 
capacity) that engages in, or plans to be engaged in (either directly or through any subsidiary or affiliate thereof), services or products offered by the Company or any of its affiliates as of
the Date of Termination that represent more than 1% of the Company’s annual revenue, or products or services that are actively being developed as part of the Company’s internal development efforts as of the Date of Termination (including,
without limitation, through the investment of capital or lending of money or property), or that manages, operates or otherwise renders any services in connection with, such business (whether on his or her own or in association with others, as a
principal, director, officer, employee, agent, representative, partner, member, security holder, consultant, advisor, independent contractor, owner, investor, participant or in any other capacity). Notwithstanding the foregoing, the Executive shall
be permitted to acquire a passive stock or equity interest in such a person or entity; provided that such stock or other equity interest acquired is less than five percent (5%) of the outstanding interest in such person or entity. 

(c) While employed by the Company and, for a period of twelve (12) months after the Date of Termination, the Executive shall not directly
or indirectly solicit, induce, or encourage any employee or consultant of any member of the Company and its subsidiaries and affiliates to terminate their employment or other relationship with the Company and its subsidiaries and affiliates or to
cease to render services to any member of the Company and its subsidiaries and affiliates and the Executive shall not initiate discussion with any such person for any such purpose or authorize or knowingly cooperate with the taking of any such
actions by any other individual or entity. During his or her employment with the Company and for a period of twelve (12) months after the Date of Termination, the Executive shall not solicit, induce, or encourage any customer, client, vendor,
or other party doing business with any member of the Company and its subsidiaries and affiliates to terminate its relationship therewith or transfer its business from any member of the Company and its subsidiaries and affiliates and the Executive
shall not initiate discussion with any such person for any such purpose or authorize or knowingly cooperate with the taking of any such actions by any other individual or entity. 

(d) In recognition of the facts that irreparable injury will result to the Company in the event of a breach by the Executive of his or her
obligations under Sections 7(a), (b) and (c) hereof, that monetary damages for such breach would not be readily calculable, and that the Company would not have an adequate remedy at law therefor, the Executive acknowledges, consents and agrees
that in the event of such breach, or the threat thereof, the Company shall be entitled, in addition to any other legal remedies and damages available, to specific performance thereof and to temporary and permanent injunctive relief (without the
necessity of posting a bond) to restrain the violation or threatened violation of such obligations by the Executive. 
 8.
Representations. The Executive hereby represents and warrants to the Company that (a) the Executive is entering into this Agreement voluntarily and that the performance of the Executive’s obligations hereunder will not violate any
agreement between the Executive and any other person, firm, organization or other entity, and (b) the Executive is not bound by the terms of any agreement with any previous employer or other party to refrain from competing, directly or
indirectly, with the business of such previous employer or other party that would be violated by the Executive’s entering into this Agreement and/or providing services to the Company pursuant to the terms of this Agreement. 

9. Successors. 
 (a) This
Agreement is personal to the Executive and, without the prior written consent of the Company, shall not be assignable by the Executive otherwise than by will or the laws of descent and distribution. This Agreement shall inure to the benefit of and
be enforceable by the Executive’s legal representatives. 

  
 8 

 (b) This Agreement shall inure to the benefit of and be binding upon the Company and its
successors and assigns (including, without limitation, EngageSmart, Inc. following the Corporate Conversion). 
 (c) The Company will require
any successor (whether direct or indirect, by purchase, merger, consolidation or otherwise) to all or substantially all of the business and/or assets of the Company to assume and agree to perform this Agreement in the same manner and to the same
extent that the Company would be required to perform it if no such succession had taken place. As used in this Agreement, “Company” shall mean the Company as hereinbefore defined and any successor to its business and/or assets as aforesaid
which assumes and agrees to perform this Agreement by operation of law, or otherwise. 
 10. Miscellaneous. 

(a) Governing Law. This Agreement shall be governed by and construed in accordance with the laws of the State of Delaware, without
reference to principles of conflict of laws. The captions of this Agreement are not part of the provisions hereof and shall have no force or effect. 

(b) Notices. All notices and other communications hereunder shall be in writing and shall be given by hand delivery to the other party
or by registered or certified mail, return receipt requested, postage prepaid, addressed as follows: 
 If to the Executive: at the
Executive’s most recent address on the records of the Company. 
 If to the Company: 

EngageSmart, Inc. 
 30 Braintree
Hill Office Park, Suite 101 
 Braintree, Massachusetts 02184 

Attn: Charles Kallenbach, General Counsel 

with a copy to: 

Latham & Watkins LLP 

1271 Avenue of the Americas 
 New
York, NY 10020 
 Attn: Bradd Williamson 
 or
to such other address as either party shall have furnished to the other in writing in accordance herewith. Notice and communications shall be effective when actually received by the addressee. 

(c) Sarbanes-Oxley Act of 2002. Notwithstanding anything herein to the contrary, if the Company determines, in its good faith judgment,
that any transfer or deemed transfer of funds hereunder is likely to be construed as a personal loan prohibited by Section 13(k) of the Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder (the
“Exchange Act”), then such transfer or deemed transfer shall not be made to the extent necessary or appropriate so as not to violate the Exchange Act and the rules and regulations promulgated thereunder. 

  
 9 

 (d) Section 409A of the Code. 

(i) To the extent applicable, this Agreement shall be interpreted in accordance with Section 409A of the Code and
Department of Treasury regulations and other interpretive guidance issued thereunder (together, “Section 409A”). Notwithstanding any provision of this Agreement to the contrary, if the Company
determines that any compensation or benefits payable under this Agreement may be subject to Section 409A, the Company shall work in good faith with the Executive to adopt such amendments to this Agreement or adopt other policies and procedures
(including amendments, policies and procedures with retroactive effect), or take any other actions, that the Company determines are necessary or appropriate to avoid the imposition of taxes under Section 409A, including without limitation,
actions intended to (i) exempt the compensation and benefits payable under this Agreement from Section 409A, and/or (ii) comply with the requirements of Section 409A; provided, however, that this
Section 10(d) shall not create an obligation on the part of the Company to adopt any such amendment, policy or procedure or take any such other action, nor shall the Company have any liability for failing to do so. 

(ii) Any right to a series of installment payments pursuant to this Agreement is to be treated as a right to a series of
separate payments. To the extent permitted under Section 409A, any separate payment or benefit under this Agreement or otherwise shall not be deemed “nonqualified deferred compensation” subject to Section 409A to the extent
provided in the exceptions in Treasury Regulation Section 1.409A-1(b)(4), Section 1.409A-1(b)(9) or any other applicable exception or provision of
Section 409A. Any payments subject to Section 409A that are subject to execution of a waiver and release which may be executed and/or revoked in a calendar year following the calendar year in which the payment event (such as termination of
employment) occurs shall commence payment only in the calendar year in which the consideration period or, if applicable, release revocation period ends, as necessary to comply with Section 409A. All payments of nonqualified deferred
compensation subject to Section 409A to be made upon a termination of employment under this Agreement may only be made upon Employee’s “separation from service” from the Company (within the meaning of Section 409A, a
“Separation from Service”). 
 (iii) To the extent that any payments or reimbursements provided to the Executive
under this Agreement are deemed to constitute compensation to the Executive to which Treasury Regulation Section 1.409A-3(i)(1)(iv) would apply, such amounts shall be paid or reimbursed reasonably
promptly, but not later than December 31 of the year following the year in which the expense was incurred. The amount of any such payments eligible for reimbursement in one year shall not affect the payments or expenses that are eligible for
payment or reimbursement in any other taxable year, and the Executive’s right to such payments or reimbursement of any such expenses shall not be subject to liquidation or exchange for any other benefit. 

(e) Severability. The invalidity or unenforceability of any provision of this Agreement shall not affect the validity or enforceability
of any other provision of this Agreement. 
 (f) Withholding. The Company may withhold from any amounts payable under this Agreement
such federal, state, local or foreign taxes as shall be required to be withheld pursuant to any applicable law or regulation. 
 (g) No
Waiver. The Executive’s or the Company’s failure to insist upon strict compliance with any provision of this Agreement or the failure to assert any right the Executive or the Company may have hereunder, including, without limitation,
the right of the Executive to terminate employment for Good Reason pursuant to Section 3(c) hereof, shall not be deemed to be a waiver of such provision or right or any other provision or right of this Agreement. 

  
 10 

 (h) Entire Agreement. As of the Effective Date, this Agreement constitutes the final,
complete and exclusive agreement between the Executive and the Company with respect to the subject matter hereof and replaces and supersedes any and all other agreements, offers or promises, whether oral or written, by any member of the Company and
its subsidiaries or affiliates, or representative thereof. Notwithstanding the foregoing, except to the extent provided herein, all equity or equity-based awards held by the Executive as of the Effective Date shall not be affected by this
Section 10(h) and shall remain in full force and effect in accordance with their terms. 
 (i) Amendment. No amendment or other
modification of this Agreement shall be effective unless made in writing and signed by the parties hereto. 
 (j) Counterparts. This
Agreement and any agreement referenced herein may be executed simultaneously in two or more counterparts, each of which shall be deemed an original but which together shall constitute one and the same instrument. 

[SIGNATURES APPEAR ON FOLLOWING PAGE] 

  
 11 

 IN WITNESS WHEREOF, the Executive has hereunto set the Executive’s hand and, pursuant
to the authorization from the Board, the Company has caused these presents to be executed in its name on its behalf, all as of the day and year first above written. 

 

			
	ENGAGESMART, LLC
		
	By:	 	 /s/ Cassandra Hudson

		 	Name: Cassandra Hudson
		 	Title: Chief Financial Officer
	
	“EXECUTIVE”
	
	 /s/ Robert Bennett

	Robert Bennett

  
 S-1 

 EXHIBIT A 

GENERAL RELEASE 
 For
valuable consideration, the receipt and adequacy of which are hereby acknowledged, the undersigned does hereby release and forever discharge the “Releasees” hereunder, consisting of EngageSmart, Inc., and its partners,
subsidiaries, associates, affiliates, successors, heirs, assigns, agents, directors, officers, employees, representatives, lawyers, insurers, and all persons acting by, through, under or in concert with them, or any of them, of and from any and all
manner of action or actions, cause or causes of action, in law or in equity, suits, debts, liens, contracts, agreements, promises, liability, claims, demands, damages, losses, costs, attorneys’ fees or expenses, of any nature whatsoever, known
or unknown, fixed or contingent (hereinafter called “Claims”), which the undersigned now has or may hereafter have against the Releasees, or any of them, by reason of any matter, cause, or thing whatsoever from the beginning
of time to the date hereof. The Claims released herein include, without limiting the generality of the foregoing, any Claims in any way arising out of, based upon, or related to the employment or termination of employment of the undersigned by
the Releasees, or any of them; any alleged breach of any express or implied contract of employment; any alleged torts or other alleged legal restrictions on Releasees’ right to terminate the employment of the undersigned; and any alleged
violation of any federal, state or local statute or ordinance including, without limitation, Title VII of the Civil Rights Act of 1964, the Age Discrimination In Employment Act, and the Americans With Disabilities Act. Notwithstanding the foregoing,
this general release (the “Release”) shall not operate to release any rights or claims of the undersigned (i) to payments or benefits under either Section [4(a) or 4(b)] of that certain Employment Agreement, effective as
of [ ● ], between [ ● ] and the undersigned (the “Employment Agreement”), whichever is applicable to the payments and benefits provided in exchange for this Release, (ii) to payments or
benefits under any equity award agreement between the undersigned and the Company, (iii) with respect to Section [2(b)(iv)] of the Employment Agreement, (iv) to accrued or vested benefits the undersigned may have, if any, as of the date
hereof under any applicable plan, policy, practice, program, contract or agreement with the Company, (v) to any Claims, including claims for indemnification and/or advancement of expenses arising under any indemnification agreement between the
undersigned and the Company or under the bylaws, certificate of incorporation or other similar governing document of the Company, (vi) to any Claims which cannot be waived by an employee under applicable law or (vii) with respect to the
undersigned’s right to communicate directly with, cooperate with, or provide information to, any federal, state or local government regulator. 

[IN ACCORDANCE WITH THE OLDER WORKERS BENEFIT PROTECTION ACT OF 1990, THE UNDERSIGNED IS HEREBY ADVISED AS FOLLOWS: 

(A) THE EXECUTIVE HAS THE RIGHT TO CONSULT WITH AN ATTORNEY BEFORE SIGNING THIS RELEASE; 

(B) THE EXECUTIVE HAS TWENTY-ONE (21) DAYS TO CONSIDER THIS RELEASE BEFORE SIGNING IT; AND 

(C) THE EXECUTIVE HAS SEVEN (7) DAYS AFTER SIGNING THIS RELEASE TO REVOKE THIS RELEASE, AND THIS RELEASE WILL BECOME EFFECTIVE UPON THE
EXPIRATION OF THAT REVOCATION PERIOD.] 
 The undersigned represents and warrants that there has been no assignment or other transfer of any
interest in any Claim which the Executive may have against Releasees, or any of them, and the undersigned agrees to indemnify and hold Releasees, and each of them, harmless from any liability, Claims, demands, damages, costs, expenses and
attorneys’ fees incurred by Releasees, or any of them, as the result of any such assignment or transfer or any rights or Claims under any such assignment or transfer. It is the intention of the parties that this indemnity does not require
payment as a condition precedent to recovery by the Releasees against the undersigned under this indemnity. 

 Notwithstanding anything herein, the undersigned acknowledges and agrees that, pursuant to
18 USC Section 1833(b), the undersigned will not be held criminally or civilly liable under any federal or state trade secret law for the disclosure of a trade secret that is made: (i) in confidence to a federal, state, or local government
official, either directly or indirectly, or to an attorney, and solely for the purpose of reporting or investigating a suspected violation of law; or (ii) in a complaint or other document filed in a lawsuit or other proceeding, if such filing
is made under seal. 
 The undersigned agrees that if the Executive hereafter commences any suit arising out of, based upon, or relating to
any of the Claims released hereunder or in any manner asserts against Releasees, or any of them, any of the Claims released hereunder, then the undersigned agrees to pay to Releasees, and each of them, in addition to any other damages caused to
Releasees thereby, all attorneys’ fees incurred by Releasees in defending or otherwise responding to said suit or Claim. 
 The
undersigned further understands and agrees that neither the payment of any sum of money nor the execution of this Release shall constitute or be construed as an admission of any liability whatsoever by the Releasees, or any of them, who have
consistently taken the position that they have no liability whatsoever to the undersigned. 
 IN WITNESS WHEREOF, the undersigned has
executed this Release this ____ day of ___________, ____. 

  
 A-2

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