Document:

EX-10.19

   

  Exhibit 10.19

   

  SIMPLE PRACTICE LLC  

  SECOND AMENDED & RESTATED EMPLOYMENT AGREEMENT 

   

  SECOND AMENDED & RESTATED EMPLOYMENT AGREEMENT (this “Agreement”) dated as of November 30, 2021 (the “Effective Date”), between SIMPLEPRACTICE, LLC, a California limited liability company, and EngageSmart, Inc., a Delaware corporation and parent of SimplePractice, LLC (collectively the “Company”), and Howard Spector (“the Employee”). 

   W I T N E S S E T H 

  WHEREAS, the Company and the Employee previously entered into that certain Employment Agreement dated March 17, 2017 (the “Prior Agreement”); and 

  WHEREAS, the Company and the Employee previously agreed to modify the Prior Agreement in an Amended and Restated Employment Agreement (“Amendment 1”); and 

  WHEREAS, the parties desire to amend and restate the Prior Agreement and Amendment 1 on the terms and conditions set forth in this Agreement. 

  NOW, THEREFORE, in consideration of the foregoing, of the mutual promises contained herein and of other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties hereto hereby agree as follows: 

  1.POSITION AND DUTIES. 

  a.During the Employment Term (as defined in Section 2 hereof), the  Employee shall serve as Founder Advisor of the Company. The Employee shall report to Robert  Bennett, Chief Executive Officer (“CEO”) of EngageSmart, LLC (“EngageSmart”). In this capacity, the Employee shall have the duties, authorities and responsibilities as set forth on Exhibit A, attached hereto, and such other duties, authorities and responsibilities as the CEO shall designate from time to time.

  b.During the Employment Term, the Employee shall use his best endeavors to promote the interests of the Company, and during the Initial Term, the Employee shall devote all of his or her business and professional time, attention, energy, skill and best efforts to the performance of his or her duties with the Company, other than for community, foundation and professional association activities and board participation, in each case, as reasonably approved by the CEO.  Employee shall coordinate with the CEO prior to each upcoming quarter to determine and prioritize duties and responsibilities for the upcoming quarter.

  c.In the event that the Employee shall discover that he has any direct or indirect material personal interest in any of the Company’s business (other than equity ownership in the Company) or a material conflict of interest with the duties required of him by virtue of his employment with the Company, the Employee shall reasonably endeavor to promptly inform Company in writing. 

  2.EMPLOYMENT TERM. The initial term of Employee’s employment under this Agreement shall commence on the Effective Date and end on December 31, 2021 (the “Initial Term”). On January 1, 2022 and each anniversary thereof, the term of this Agreement shall be automatically extended for successive one year periods unless either the Company or the 

   

  

   

  Employee elects not to extend this Agreement by giving at least sixty (60) days’ advance written notice of non-renewal to the other party that the Employment Term shall not be extended (each such subsequent term, a “Subsequent Term” and collectively the “Subsequent Terms”). The Initial Term and any Subsequent Terms shall constitute the “Term” for purposes of this Agreement. Notwithstanding the foregoing, the Employee’s employment hereunder may be earlier terminated in accordance with Section 5 hereof, subject to Section 6 hereof. The period of time between the Effective Date and the termination of the Employee’s employment hereunder shall be referred to herein as the “Employment Term.” 

  3.COMPENSATION.

  a.BASE SALARY. The Company agrees to pay the Employee a base salary at an annual rate of not less than $600,000 during the Initial Term and $120,000 during any Subsequent Term, in each case less applicable payroll and tax withholdings, payable in accordance with the regular payroll practices of the Company. The base salary as determined herein from time to time shall constitute “Base Salary” for purposes of this Agreement.

  b.BONUS OPPORTUNITY. During the Initial Term, the Employee will continue to be eligible to participate in the Company’s performance-based incentive programs, as may be in effect from time to time in accordance with the Company’s compensation practices and the terms and provisions of such programs, as established by the Company in its sole discretion; provided that the Employee shall have an annual target incentive opportunity of up to forty percent (40%) of his Base Salary then in effect; and further provided that the Employee must be employed with the Company on the last date of the year for which any such bonus is earned. During any Subsequent Terms, the Employee will not be eligible to participate in any Company’s annual bonus or other performance-based incentive programs. 

  4.EMPLOYEE BENEFITS.

  a.BENEFIT PLANS. The Employee shall be entitled to participate in any employee benefit plan that the Company has adopted or may adopt, maintain or contribute to for the benefit of its employees generally from time to time, subject to satisfying the applicable eligibility requirements. Notwithstanding the foregoing, the Company may modify or terminate any employee benefit plan at any time. To the extent that the level of such benefits is based on seniority or compensation levels, the Company shall make appropriate and proportionate adjustments to the Employee’s benefits. The Employee shall be further entitled to the following additional benefits which shall supplement or replace, to the extent duplicative of any part or all of the general officer benefits, the benefits otherwise provided to the Employee.

  b.VACATION. The Employee shall be entitled to paid vacation (or other paid time off) per calendar year (subject to proration for any partial years) in accordance with the Company’s policy on accrual and use applicable to similarly situated employees as in effect from time to time.

  c.BUSINESS EXPENSES. Upon presentation of appropriate documentation, the Employee shall be reimbursed in accordance with the Company’s expense reimbursement policy, for reasonable business expenses incurred in connection with the performance of the Employee’s duties hereunder and the Company’s policies with regard thereto.

  5.TERMINATION. The Employee’s employment and the Employment Term shall terminate on the first of the following to occur: 

   

  

   

  a.DISABILITY. Upon ten (10) days’ prior written notice by the Company to the Employee of termination due to Disability. For purposes of this Agreement, “Disability” shall be defined as the inability of the Employee to perform the Employee’s material duties hereunder with or without reasonable accommodation due to a physical or mental injury, infirmity or incapacity for one hundred twenty (120) days (including weekends and holidays) in any consecutive 365-day period, as determined by the Company in its sole discretion.

  b.DEATH. Automatically on the date of death of the Employee.

  c.CAUSE. Immediately upon written notice by the Company to the Employee in accordance with this Agreement of a termination for Cause. “Cause” shall mean:

  i.the Employee’s abandonment of, or willful misconduct or gross negligence in the performance of Employee’s duties to the Company or any of its affiliates, after there has been delivered to Employee by Company a written demand for performance and ten (10) Business day opportunity to cure which sets forth in reasonable detail the allegation in which Company believes that Employee has not substantially performed Employee’s duties;

  ii.the Employee’s willful failure to follow the lawful directives of the Company or the Employee’s willful failure to perform the Employee’s duties to the Company or any of its affiliates, in each case, other than as a result of death or Disability;

  iii.the Employee’s commission of, indictment for, conviction of, or pleading of guilty or nolo contendere to, a felony or any crime involving moral turpitude;

  iv.any act by the Employee of theft, misappropriation, fraud, malfeasance or dishonesty in connection with the Employee’s position, duties or responsibilities hereunder;

  v.the Employee’s breach of this Agreement (including, but not limited to, Sections 8 and 9 hereof) or any other agreement between the Employee and the Company;

  vi.the Employee’s violation of Section 6.02 of the Securities Purchase Agreement, dated as of Effective Date by and between EngageSmart and various equityholders named therein (the “SPA”);

  vii.the Employee’s breach of the Company’s (or any of its affiliates’)  code of conduct, code of ethics or other written policy; or

  viii.the Employee’s breach of any fiduciary duty or responsibility owed by him or her to the Company or any of its affiliates; 

  provided that, in the cases of the foregoing clauses (i), (ii), (v), (vi) and (vii), the Employee has not cured such reason within ten (10) Business days after being notified of such reason by the Company; provided, further, that during such cure period, the Company may elect to prevent the Employee from acting in his capacity at the Company.

  Any determination of Cause hereunder shall be made by the CEO of the Company (or successor governing body thereof) in the CEO’s sole discretion.

  d.GOOD REASON. Upon written notice by the Employee to the Company of a termination for Good Reason. “Good Reason” shall mean the occurrence of any of the following events, without the prior written consent of the Employee:

   

  

   

  i.reduction in the Employee’s Base Salary (other than any reduction that is necessary to maintain the solvency of the Company);

  ii.material diminution in the Employee’s duties, responsibilities or level of authority (other than temporarily while physically or mentally incapacitated or as required by applicable law); or

  iii.relocation of the Employee’s principal place of employment to a location more than 35 miles from his or her then current principal place of employment. 

  provided that “Good Reason” shall only be deemed to have occurred if, no later than thirty (30) days following the initial occurrence of the circumstances constituting “Good Reason,” Employee provides a written notice to the Company containing reasonable details of such circumstances and within thirty (30) days following the delivery of such notice to the Company, the Company has failed to cure such circumstances. Additionally, Employee must terminate his or her employment within ninety (90) days of the initial occurrence of the circumstances constituting “Good Reason” for such termination to be “Good Reason” hereunder. Otherwise, any claim that the facts and circumstances giving rise to such “Good Reason” constitute “Good Reason” hereunder shall be deemed irrevocably waived by the Employee. 

  e.WITHOUT GOOD REASON. Upon thirty (30) days’ prior written notice by the Employee to the Company of the Employee’s voluntary termination of employment without Good Reason (which the Company may, in its sole discretion, make effective earlier than any notice date). 

  f.EXPIRATION OF TERM. Upon the expiration of the Term pursuant to the provisions of Section 2 hereof.

  6.CONSEQUENCES OF TERMINATION.

  a.DEATH. In the event that the Employee’s employment and the Employment Term ends on account of the Employee’s death, the Employee, the Employee’s estate (or to the extent a beneficiary has been validly designated, such beneficiary), as the case may be, shall be entitled to the following: 

  i.any unpaid Base Salary through the date of termination and any accrued vacation in accordance with the then applicable Company vacation policy;

  ii.any unpaid incentive bonus accrued and earned pursuant to Section 3(b) hereof for any quarterly bonus period ending on or prior to the date of termination;

  iii.reimbursement for any unreimbursed business expenses incurred through the date of termination in accordance with the then applicable Company expense reimbursement policy; and 

  iv.all other vested payments or benefits to which the Employee is entitled under the terms of any applicable employee benefit plan (collectively, 6(a)(i) through 6(a)(iv) hereof shall be hereafter referred to as the “Accrued Benefits”). 

  b.DISABILITY. In the event that the Employee’s employment and/or  Employment Term ends on account of the Employee’s Disability, the Company shall pay or provide the Employee with the Accrued Benefits.

  c.TERMINATION FOR CAUSE OR WITHOUT GOOD REASON OR DUE TO NON-RENEWAL BY THE EMPLOYEE. If, during the Initial Term, the Employee’s employment is terminated (x) by the Company for Cause, or (y) by the Employee 

   

  

   

  without Good Reason, or (z) due to the expiration of the Initial Term due to non-renewal by the Employee as provided in Section 2 hereof, the Company shall pay to the Employee the Accrued Benefits.

  d.TERMINATION WITHOUT CAUSE OR FOR GOOD REASON. If, during the Initial Term, the Employee’s employment is terminated (y) by the Company without Cause, (z) by the Employee for Good Reason, the Company shall pay or provide the Employee with the following, subject to the provisions of Section 17 hereof:

  i.the Accrued Benefits; 

  ii.subject to the Employee’s compliance with the obligations in Sections 7, 8 and 9 hereof, the continuation of the Employee’s Base Salary and health and welfare benefits, in each case, as then in effect and in accordance with the Company’s standard payroll and benefit policies (such continuation payments, the “Severance Payments”) for the six (6) month period following termination; and

  iii.notwithstanding anything to the contrary in the Hancock Parent, LLC Amended and Restated 2015 Stock Option Plan (the “2015 Plan”) or any stock option award agreement or other documentation underlying any stock option awarded to Employee thereunder prior to the Effective Date (each, an “Option”), all outstanding Options held by the Employee as of the date of such termination shall remain outstanding through April 2, 2022 and shall continue vesting through April 2, 2022, at such time(s) as the Options (or portion thereof) would have vested had Employee remained employed by the Company through April 2, 2022. 

  Payments and benefits provided in this Section 6(d) shall be in lieu of any termination or severance payments or benefits for which the Employee may be eligible under any of the plans, policies or programs of the Company or under the Worker Adjustment Retraining Notification Act of 1988 or any similar state statute or regulation.

  e.TERMINATION AND CHANGE OF CONTROL. In the event of a Change of Control of  the Company, if, following such Change of Control but during the Initial Term (x) the Employee’s employment is terminated, or (y) without Employee’s written consent there occurs any material adverse change in the nature and scope of the Employee’s position, responsibilities, duties, or a change of 35 miles or more in the Employee’s location of employment, or any material reduction in Employee’s compensation or benefits and Employee voluntarily terminates his employment, then the Company shall pay or provide the Employee with the following, subject to the provisions of Section 17 hereof: 

  i.the Accrued Benefits; and

  ii.subject to the Employee’s compliance with the obligations in Sections 7, 8 and 9 hereof, the continuation of the Employee’s Base Salary and health and welfare benefits, in each case, as then in effect and in accordance with the Company’s standard payroll and benefit policies (such continuation payments, the “Severance Payments”) for the six (6) month period following termination; 

  Payments and benefits provided in this Section 6 shall be in lieu of any termination or severance payments or benefits for which the Employee may be eligible under any of the plans, policies or programs of the Company or under the Worker Adjustment Retraining Notification Act of 1988 or any similar state statute or regulation. For purposes of this Agreement, “Change of Control” means, with 

   

  

   

  respect to a party, the consummation of a transaction (or series of related transactions), the voluntary or involuntary liquidation, dissolution or winding up where (A) such party sells, licenses, conveys or otherwise disposes of all or substantially all of its and its subsidiaries (taken as a whole) assets, property or business in one or a series of transactions, (B) any Person or group of Persons, other than the stockholders (or their Affiliates) of such party and such Persons (who are not Affiliates of any of the stockholders of such party) acquire 50% or more of the voting stock of such party, in one or a series of transactions, whether or not such party is a party to such transaction(s), or (C) such party merges or consolidates with or into any other corporation, limited liability company or other entity (other than an Affiliate of such party or any Affiliate of any stockholder of such party), other than a merger or consolidation in which the stockholders (or their Affiliates) of such party continue to hold 50% or more of the voting stock of such party (“Business Combination”). However, a Change of Control will not include (1) any consolidation or merger effected exclusively to change the domicile of such party, or (2) any transaction or series of transactions which are restructuring for tax purposes, or (3) any transaction or series of transactions principally for bona fide equity financing purposes in which cash is received by such party or any successor or indebtedness of such party is cancelled or converted or a combination thereof; provided further, a private equity or venture capital financing of any of such party or any Affiliate, through the sale of shares or other equity in such party, which financing is led by one or more venture capital or private equity funds, for the primary purpose of raising capital for use in the operations of such party, or any internal reorganization, shall not be considered a Change of Control.

  For purposes of this Agreement, “Change of Control Period” means the period of time (a) commencing on the earlier of (i) one hundred twenty (120) days before the date the Change of Control occurs, or if earlier, one hundred twenty (120) days before a definitive agreement is executed by the Company  for a Business Combination (provided, however, that in the event of this subsection (a)(i) the Employee reasonably demonstrates that his termination of employment should it occur was either (x) at the request of a third party who has taken steps reasonably calculated to effect a Change of Control, or (y) otherwise arose in connection with a Change of Control), or (ii) the date the Change of Control occurs, and (b) ending on the last day of the twelfth (12th) calendar month immediately following the month the Change of Control occurred.

  f.TERMINATION DURING ANY SUBSEQUENT TERM. Notwithstanding anything else in this Agreement to the Contrary, in the event the Employee’s employment is terminated for any reason during a Subsequent Term, the Company shall pay to the Employee only the Accrued Benefits; provided, however, that, notwithstanding anything to the contrary in the 2015 Plan or any stock option award agreement or other documentation underlying any Option, all outstanding Options held by the Employee as of the date of such termination shall remain outstanding through April 2, 2022 and shall continue vesting through April 2, 2022, at such time(s) as the Options (or portion thereof) would have vested had Employee remained employed by the Company through April 2, 2022.

  g.OTHER OBLIGATIONS. Upon any termination of the Employee’s employment with the Company for Cause, the Employee shall promptly resign from the Company and any other position as an officer, director or fiduciary of the Company or any of its affiliates.

   

  

   

  7.RELEASE; NO MITIGATION. Any and all amounts payable and benefits or additional rights provided pursuant to this Agreement beyond the Accrued Benefits shall only be payable if the Employee delivers to the Company and does not revoke a general release of claims in favor of the Company and its present and former owners, members, officers, directors, agents, attorneys and affiliates in a form provided to the Employee by the Company within twenty one (21) days of employment termination (which release shall not include any claims in respect of such Employee’s equity ownership of the Company, or the agreements related thereto (e.g., a stockholders agreement). Such release shall be executed and delivered by the Employee to the Company (and no longer subject to revocation, if applicable) within sixty (60) days of termination.

  8.CERTAIN COVENANTS.

  a.CONFIDENTIALITY. As a condition of Employee’s employment, Employee shall sign and comply with all agreements governing the protection of confidential information and trade secrets. In addition, Employee further agrees that the Employee shall not, directly or indirectly, use, make available, sell, disclose or otherwise communicate to any person, other than in the course of the Employee’s assigned duties and for the benefit of the Company, either during the period of the Employee’s employment or at any time thereafter, any business and technical information or trade secrets, nonpublic, proprietary or confidential information, knowledge or data relating to the Company, any of its subsidiaries, affiliated companies or businesses, or their customers, which shall have been obtained by the Employee during the Employee’s employment by the Company (or any predecessor) (“Confidential Information.”). The foregoing shall not apply to information that (A) was known to the public prior to its disclosure to the Employee; or (B) becomes generally known to the public subsequent to disclosure to the Employee through no wrongful act of the Employee or any representative of the Employee. Employee may disclose Confidential Information to the extent that such disclosure is required by law or court order, provided, however, that Employee promptly provides to the CEO prior written notice of such disclosure and provides assistance in obtaining an order or other remedy protecting the Confidential Information from public disclosure. In the event that such disclosure is required, Employee will furnish only that portion of the Confidential Information as is legally required and will exercise reasonable efforts to ensure that the Confidential Information will be treated as confidential. The terms and conditions of this Agreement shall remain strictly confidential, and the Employee hereby agrees not to disclose the terms and conditions hereof to any person or entity, other than immediate family members, legal advisors or personal tax or financial advisors, or prospective future employers solely for the purpose of disclosing the limitations on the Employee’s conduct imposed by the provisions of this Section 8. However, nothing in this Section 8(a), nor any other portion of this Agreement, prohibits Employee from reporting an event that he reasonably and in good faith believes is a violation of law to the relevant law-enforcement agency (such as the Securities and Exchange Commission, Equal Employment Opportunity Commission, or Department of Labor), or from cooperating in an investigation conducted by such a government agency. Employee acknowledges that he has received notice, and understands, that under the 2016 Defend Trade Secrets Act (DTSA): (1) no individual will be held criminally or civilly liable under Federal or State trade secret law for the disclosure of a trade secret (as defined under the DTSA) that: (a) is made in confidence to a Federal, State, or local government official, either directly or indirectly, or to an attorney; and made solely for the purpose of reporting or investigating a suspected violation of law; or, (b) is made in a complaint or other document filed in a lawsuit or other proceeding, if such filing is made under seal so that it is not made public; and, (2) an individual who pursues a lawsuit for retaliation for 

   

  

   

  reporting a suspected violation of the law may disclose the trade secret to the attorney of the individual and use the trade secret information in the court proceeding, if the individual files any document containing the trade secret under seal, and does not disclose the trade secret, except as permitted by court order.

  b.NONSOLICITATION; NONINTERFERENCE.

  i.During the Employee’s employment with the Company and thereafter, Employee agrees not to disclose or use the Company’s Confidential Information including its trade secrets in order to solicit, aid or induce any customer of the Company to terminate its relationship with the Company or to purchase goods or services from any competitor.

  ii.During the Employee’s employment with the Company and for a period of twelve (12) months thereafter, the Employee agrees that the Employee shall not, except in the furtherance of the Employee’s duties hereunder, directly or indirectly, individually or on behalf of any other person, firm, corporation or other entity, (A) solicit, aid or induce any employee, representative or agent of the Company or any of its subsidiaries or affiliates to leave such employment or to terminate such relationship with the Company, or (B) unlawfully interfere with the contractual relationship between the Company or any of its subsidiaries or affiliates and any of their respective vendors, joint venturers or licensors. An employee, representative or agent shall be deemed covered by this Section 8(b)(ii) while so employed or retained.

  c.NONDISPARAGMENT. During and following the Employee’s employment with the Company, the Employee agrees not to make negative comments or otherwise disparage the Company or its officers, members, directors, employees, shareholders, affiliates, agents or products, in any manner likely to be harmful to them or their business, business reputation or personal reputation other than while employed by the Company, in the good faith performance of the Employee’s duties to the Company. The foregoing shall not be violated by truthful statements in response to legal process, required governmental testimony or filings, or administrative or arbitral proceedings (including, without limitation, depositions in connection with such proceedings).

  d.INVENTIONS. 

  i.The Employee acknowledges and agrees that all ideas, methods, inventions, discoveries, improvements, work products or developments (“Inventions”), whether patentable or unpatentable, (A) that relate to the Employee’s work with the Company, made or conceived by the Employee, solely or jointly with others, during the Employment Term, or (B) suggested by any work that the Employee performs in connection with the Company, either while performing the Employee’s duties with the Company or on the Employee’s own time, but only insofar as the Inventions are related to the Employee’s work as an employee or other service provider to the Company, shall belong exclusively to the Company (or its designee), whether or not patent applications are filed thereon. The Employee will keep full and complete written records (the “Records”), in the manner prescribed by the Company, of all Inventions, and will promptly disclose all Inventions completely and in writing to the Company. The Records shall be the sole and exclusive property of the Company, and the Employee will surrender them upon the termination of the Employment Term, or upon the Company’s request. The Employee will assign and hereby does assign to the Company the Inventions and all patents that may issue thereon in any and all countries, whether during or 

   

  

   

  subsequent to the Employment Term, together with the right to file, in the Employee’s name or in the name of the Company (or its designee), applications for patents and equivalent rights (the “Applications”). The Employee shall, at any time during and subsequent to the Employment Term, make such applications, sign such papers, take all rightful oaths, and perform all acts as may be requested from time to time by the Company with respect to the Inventions. The Employee shall also execute such further assignments and hereby makes such assignments to the Company (or its designee) of the Applications, and give the Company and its attorneys all reasonable assistance (including the giving of testimony) to obtain the Inventions for its benefit, all without additional compensation to the Employee from the Company, but entirely at the Company’s expense.

  ii.In addition, the Inventions will be deemed Work for Hire, as such term is defined under the copyright laws of the United States, on behalf of the Company and the Employee agrees that the Company will be the sole owner of the Inventions, and all underlying rights therein, in all media now known or hereinafter devised, throughout the universe and in perpetuity without any further obligations to the Employee (other than as set forth expressly in this Agreement). If the Inventions, or any portion thereof, are deemed not to be Work for Hire, the Employee hereby irrevocably conveys, transfers and assigns to the Company, all rights, in all media now known or hereinafter devised, throughout the universe and in perpetuity, in and to the Inventions, including, without limitation, all of the Employee’s right, title and interest in the copyrights (and all renewals, revivals and extensions thereof) to the Inventions, including, without limitation, all rights of any kind or any nature now or hereafter recognized, including without limitation, the unrestricted right to make modifications, adaptations and revisions to the Inventions, to exploit and allow others to exploit the Inventions and all rights to sue at law or in equity for any infringement, or other unauthorized use or conduct in derogation of the Inventions, known or unknown, prior to the date hereof, including, without limitation, the right to receive all proceeds and damages therefrom. In addition, the Employee hereby waives any so-called “moral rights” with respect to the Inventions. The Employee hereby waives any and all currently existing and future monetary rights in and to the Inventions and all patents that may issue thereon, including, without limitation, any rights that would otherwise accrue to the Employee’s benefit by virtue of the Employee being an employee of or other service provider to the Company.

  iii.Employee understands that Inventions (as defined above) do not include, and the obligations of this Section 8(d) do not apply to, subject matter that meets all of the following criteria: (1) is conceived, developed and created by Employee on Employee’s own time without using the Company’s equipment, supplies or facilities or any Confidential Information or trade secrets, (2) is unrelated to the actual or reasonably anticipated business or research and development of the Company of which Employee is or becomes aware, and (3) does not result from any work performed by Employee for the Company; provided, further, nothing in this Agreement shall be construed to require Employee to assign to the Company any Inventions that are excluded from any such assignment under California Labor Code section 2870. A copy of California Labor Code section 2870 will be provided to Employee upon written request or may be located on the internet and is reproduced under Exhibit C. Employee shall be deemed to be aware of all activities of the Company.

   

  

   

  iv.To avoid any misunderstanding, Employee has listed on Exhibit B (1) all materials, creations, designs, technology, discoveries, inventions, ideas, information and other subject matter, including, but not limited to, copyrights, trade secrets, patents, trademarks and other intellectual property rights, if any, developed or created by Employee, alone or with others, before the period of Employee’s employment with the Company in which Employee claims any ownership or rights, and (2) all agreements or arrangements that may affect the rights to any such subject matter or Employee’s ability to be employed by and perform services for the Company and comply with the requirements of this Agreement. Employee acknowledges and agrees that (i) by not listing particular subject matter, Employee is warranting that the subject matter was not conceived, developed or created before commencement of Employee’s employment, and (ii) by not listing particular agreements or arrangements, Employee is warranting that no such agreements or arrangements exist.

  e.RETURN OF COMPANY PROPERTY. On the date of the Employee’s termination of employment with the Company for any reason (or at any time prior thereto at the Company’s request);, the Employee shall return all property belonging to the Company or its affiliates (including, but not limited to, any Company-provided laptops, computers, cell phones, wireless electronic mail devices or other equipment, or documents and property belonging to the Company) and all Confidential Information and Employee shall not be authorized to retain any copies of any such Confidential Information.

  f.SEVERABILITY. The Employee acknowledges that the restrictions contained in this Section 8 are reasonable and necessary to protect the legitimate interests of the Company and constitute a material inducement to the Company to enter into this Agreement. The covenants contained in this Section 8 and each provision hereof are severable and distinct covenants and provisions. The invalidity or unenforceability of any such covenant or provision as written shall not invalidate or render unenforceable the remaining covenants or provisions hereof, and any such invalidity or unenforceability in any jurisdiction shall not invalidate or render unenforceable such covenant or provision in any other jurisdiction. 

  g.TOLLING. In the event of any violation of the provisions of this Section 8, the Employee acknowledges and agrees that the post-termination restrictions contained in this Section 8 shall be extended by a period of time equal to the period of such violation, it being the intention of the parties hereto that the running of the applicable post-termination restriction period shall be tolled during any period of such violation.

  h.ACKNOWLEDGEMENT REGARDING RESTRICTIVE COVENANTS. Employee acknowledges and agrees that (i) he has signed or will sign other agreements or arrangements in connection with consummating the transactions contemplated by the SPA (ii) such other agreements or arrangements may contain restrictive covenants, and (iii) any such restrictive covenants may be similar to, or may be different from, the restrictive covenants contained in this Agreement. Unless explicitly set forth in any such agreement or arrangement, any such restrictions will be in addition to, and will not serve to limit or be in lieu of, the restrictions set forth in this Agreement.

  i.SURVIVAL OF PROVISIONS. The obligations contained in Sections 8  and 9 hereof shall survive the termination or expiration of the Employment Term and the Employee’s employment with the Company and shall be fully enforceable thereafter.

  9.COOPERATION. Upon the receipt of notice from the CEO (including outside counsel), the Employee agrees that while employed by the Company and thereafter, the Employee will 

   

  

   

  respond and provide information with regard to matters in which the Employee has knowledge as a result of the Employee’s employment with the Company, and will provide reasonable assistance to the Company, its affiliates and their respective representatives in defense of any claims that may be made against the Company or its affiliates, and will assist the Company and its affiliates in the prosecution of any claims that may be made by the Company or its affiliates, to the extent that such claims may relate to the period of the Employee’s employment with the Company. The Employee agrees to promptly inform the CEO if the Employee becomes aware of any lawsuits involving such claims that may be filed or threatened against the Company or its affiliates. The Employee also agrees to promptly inform the CEO (to the extent that the Employee is legally permitted to do so) if the Employee is asked to assist in any investigation of the Company or its affiliates (or their actions), regardless of whether a lawsuit or other proceeding has then been filed against the Company or its affiliates with respect to such investigation, and shall not do so unless legally required. Upon presentation of appropriate documentation, the Company shall pay or reimburse the Employee for all reasonable out-of-pocket travel, duplicating or telephonic expenses incurred by the Employee in complying with this Section 9.

  10.EQUITABLE RELIEF AND OTHER REMEDIES. The Employee acknowledges and agrees that the Company’s remedies at law for a breach or threatened breach of any of the provisions of Section 8 or Section 9 hereof would be inadequate and, in recognition of this fact, the Employee agrees that, in the event of such a breach or threatened breach, in addition to any remedies at law, the Company, without posting any bond, shall be entitled to obtain equitable relief in the form of specific performance, a temporary restraining order, a temporary or permanent injunction or any other equitable remedy which may then be available. In the event of a violation by the Employee of Section 8 or Section 9 hereof, any severance being paid to the Employee pursuant to this Agreement or otherwise shall immediately cease, and any severance previously paid to the Employee (other than $1,000) shall be immediately repaid to the Company.

  11.NO ASSIGNMENTS. This Agreement is personal to each of the parties hereto. Except as provided in this Section 11 hereof, no party may assign or delegate any rights or obligations hereunder without first obtaining the written consent of the other party hereto. The Company may assign this Agreement to any successor to all or substantially all of the business and/or assets of the Company.

  12.NOTICE. For purposes of this Agreement, notices and all other communications provided for in this Agreement shall be in writing and shall be deemed to have been duly given (a) on the date of delivery, if delivered by hand, (b) on the date of transmission, if delivered by confirmed facsimile or electronic mail, (c) on the first business day following the date of deposit, if delivered by guaranteed overnight delivery service, or (d) on the fourth business day following the date delivered or mailed by United States registered or certified mail, return receipt requested, postage prepaid, addressed as follows: 

  If to the Employee: 

  At the address (or to the facsimile number) shown on the records of the Company 

  If to the Company:

  EngageSmart, LLC c/o EngageSmart, LLC

  30 Braintree Hill Office Park, Suite 303 Braintree, MA 02184

  Attention: CEO, and General Counsel

  With a copy to: 

   

  

   

  Latham & Watkins LLP

  1271 Avenue of the Americas

  New York, NY 10020

  Attention: Bradd Williamson, Esq.

  or to such other address as either party may have furnished to the other in writing in accordance herewith, except that notices of change of address shall be effective only upon receipt.

  13.SECTION HEADINGS; INCONSISTENCY. The section headings used in this Agreement are included solely for convenience and shall not affect, or be used in connection with, the interpretation of this Agreement. In the event of any inconsistency between the terms of this Agreement and any form, award, plan or policy of the Company, the terms of this Agreement shall govern and control.

  14.SEVERABILITY. The provisions of this Agreement shall be deemed severable and the invalidity or unenforceability of any provision shall not affect the validity or enforceability of the other provisions hereof.

  15.COUNTERPARTS. This Agreement may be executed in several counterparts, each of which shall be deemed to be an original but all of which together will constitute one and the same instrument.

  16.MISCELLANEOUS. No provision of this Agreement may be modified, waived or discharged unless such waiver, modification or discharge is agreed to in writing and signed by the Employee and such officer or director as may be designated by Company. No waiver by either party hereto at any time of any breach by the other party hereto of, or compliance with, any condition or provision of this Agreement to be performed by such other party shall be deemed a waiver of similar or dissimilar provisions or conditions at the same or at any prior or subsequent time. This Agreement together with all exhibits hereto sets forth the entire agreement of the parties hereto in respect of the subject matter contained herein and supersedes any and all prior agreements or understandings between the Employee and the Company with respect to the subject matter hereof. No agreements or representations, oral or otherwise, express or implied, with respect to the subject matter hereof have been made by either party which are not expressly set forth in this Agreement. The validity, interpretation, construction and performance of this Agreement shall be governed by the laws of the State of California without regard to the choice of law principles thereof. Any action which in any way involves the rights, duties and obligations of the parties hereunder shall be brought in the courts of the State of Illinois and venue for any action or proceeding shall be in Cook County, Illinois or in the United States District Court for the Northern District of Illinois, and the parties hereby submit to the personal jurisdiction of said courts. In the event of litigation or any other action or proceeding between the parties to interpret or enforce this Agreement, or any part thereof or relating to this Agreement, the prevailing party shall be entitled to recover its costs related to such action or proceeding and its reasonable fees of attorneys, accountants and expert witnesses incurred by such party in connection with any such action or proceedings. The prevailing party shall be deemed to be the party which obtains substantially the relief sought by final resolution, compromise or settlement, or as may otherwise be determined by order of a court of competent jurisdiction in the event of litigation, an award or decision of an arbitrator in the event of arbitration. This provision is subject to Section 4 of Exhibit B (Earnout) of the SPA, which Section 4 shall take precedence in the event of any dispute regarding Exhibit B, and which determination shall be binding on the Parties as it relates to this Agreement.

  17.REPRESENTATIONS. The Employee represents and warrants to the Company that (a) the Employee has the legal right to enter into this Agreement and to perform all of the obligations 

   

  

   

  on the Employee’s part to be performed hereunder in accordance with its terms, and (b) the Employee is not a party to any agreement or understanding, written or oral, and is not subject to any restriction, which, in either case, could prevent the Employee from entering into this Agreement or performing all of the Employee’s duties and obligations hereunder.

  18.INDEMNITY. The Company shall indemnify and hold the Employee harmless from any cost, expense or liability arising out of or relating to any acts or decisions made by the Employee on behalf of or in the course of performing services for the Company to the same extent the Company indemnifies and holds harmless the CEO of the Company and in accordance with the articles of organization and operating agreement of the Company.

  19.TAX MATTERS.

  a.WITHHOLDING. The Company may withhold from any and all amounts  payable under this Agreement such federal, state and local taxes as may be required to be withheld pursuant to any applicable law or regulation.

  b.SECTION 409A COMPLIANCE.

  i.The intent of the parties is that payments and benefits under this Agreement be exempt from, or comply with, Internal Revenue Code Section 409A and the regulations promulgated thereunder (collectively “Code Section 409A”) and shall be interpreted to be in a manner consistent with such intention. In no event whatsoever shall the Company be liable for any additional tax, interest or penalty that may be imposed on the Employee by Code Section 409A or any damages for failing to comply with Code Section 409A.

  ii.A termination of employment shall not be deemed to have occurred for purposes of any provision of this Agreement providing for the payment of any amounts or benefits upon or following a termination of employment unless such termination is also a “separation from service” within the meaning of Code Section 409A and, for purposes of any such provision of this Agreement, references to a “termination,” “termination of employment” or like terms shall mean “separation from service.” If the Employee is deemed on the date of termination to be a “specified employee” within the meaning of that term under Code Section 409A(a)(2)(B), then with regard to any payment or the provision of any benefit that is specified as subject to this section or that is otherwise considered deferred compensation under Code Section 409A payable on account of a “separation from service,” such payment or benefit shall be made or provided at the date which is the earlier of (A) the expiration of the six (6)-month period measured from the date of such “separation from service” of the Employee, and (B) the date of the Employee’s death (the “Delay Period”). Upon the expiration of the Delay Period, all payments and benefits delayed pursuant to this Section 19(b)(ii) (whether they would have otherwise been payable in a single sum or in installments in the absence of such delay) shall be paid or reimbursed to the Employee in a lump sum and any remaining payments and benefits due under this Agreement shall be paid or provided in accordance with the normal payment dates specified for them herein.

  iii.All expenses or other reimbursements under Sections 4(c) and 9 hereof shall be made on or prior to the last day of the taxable year following the taxable year in which such expenses were incurred by the Employee (provided that if any such reimbursements constitute taxable income to the Employee, such reimbursements shall be paid no later than March 15th of the calendar year following the calendar year in which the expenses to be reimbursed were incurred), and no such 

   

  

   

  reimbursement or expenses eligible for reimbursement in any taxable year shall in any way affect the expenses eligible for reimbursement in any other taxable year. 

  iv.For purposes of Code Section 409A, the Employee’s right to receive any installment payments pursuant to this Agreement shall be treated as a right to receive a series of separate and distinct payments. Whenever a payment under this Agreement specifies a payment period with reference to a number of days (e.g., “payment shall be made within thirty (30) days following the date of termination”), the actual date of payment within the specified period shall be within the sole discretion of the Company. 

    

    

  [REMAINDER OF PAGE INTENTIONALLY LEFT BLANK]

   

   

   

   

  

   

   

  IN WITNESS WHEREOF, the parties hereto have executed this Agreement as of the date first written above. 

   

  	
	ENGAGESMART, INC.

	 

	By: /s/ Robert Bennett

	Name: Robert Bennett

	Title: Chief Executive Officer

	 

	 

	EMPLOYEE:

	 

	/s/ Howard Spector

	Name: Howard Spector

   

   

   

  

   

   

  Job Duties/Responsibilities 

    

    

  Initial Term: 

    

  Employee’s primary responsibility includes assisting SimplePractice President with a successful transition of day-to-day management and continuing to support the President with the execution of the 2021 operating plan.  In addition, unless on pre-approved vacation, Employee shall participate in weekly one-on-one meetings with SimplePractice President and COO and EngageSmart CEO. 

    

  Subsequent Terms: 

    

  Employee’s primary responsibility includes assisting the EngageSmart CEO with vision, strategy, execution, culture, and innovation across all EngageSmart solutions.  Employee shall participate as reasonably requested by the Company with M&A activities.  In addition, Employee shall schedule regular status meetings with EngageSmart CEO, on a basis and frequency as jointly agreed upon between Employee and the EngageSmart CEO, to determine any changes, additions, and or deletions to Employee’s list of responsibilities.

   

   

  

   

   

  Reserved Inventions: Related Agreements or Arrangements 

  None.

   

   

  

   

   

  California Labor Code Section 2870 

    

  (a)Any provision in an employment agreement which provides that an employee shall assign, or offer to assign, any of his or her rights in an invention to his or her employer shall not apply to an invention that the employee developed entirely on his or her own time without using the employer's equipment, supplies, facilities, or trade secret information except for those inventions that either: 

    

  (1)Relate at the time of conception or reduction to practice of the invention to the employer's business, or actual or demonstrably anticipated research or development of the employer; or 

    

  (2)Result from any work performed by the employee for the employer. 

    

  To the extent a provision in an employment agreement purports to require an employee to assign an invention otherwise excluded from being required to be assigned under subdivision (a), the provision is against the public policy of this state and is unenforceable.EX-10.20

   

  Exhibit 10.20

   

  EMPLOYMENT AGREEMENT

  THIS EMPLOYMENT AGREEMENT (this “Agreement”) is entered into by and between EngageSmart, Inc. (the “Company”) and Kevin O’Brien (the “Executive”) as of February 1, 2022 (the “Effective Date”).

  WHEREAS, the Executive is to be employed as President, Enterprise of the Company;

  WHEREAS, in connection with Executive’s employment, 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 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 third 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 Extension 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.

  2.Terms of Employment.

  a.Position and Duties.

  i.Role and Responsibilities.  During the Employment Period, the Executive shall serve as President, Enterprise of the Company, and shall perform such employment duties as are usual and customary for such positions.  The Executive shall report directly to the Chief Executive Officer of the Company (or his or her designee).  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 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, (B) fulfill limited teaching, speaking and writing engagements, and (C) manage his 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 $450,000 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 set at fifty percent (50%) 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.

  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 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 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 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 time off in accordance with the plans, policies, programs and practices of the Company applicable to its employees in effect from time to time.

  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 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;

  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 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.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 earned but unpaid Base Salary and accrued but unpaid vacation pay through the date of such termination (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 9-month anniversary of the Date of Termination in installments in accordance with the Company’s regular payroll practices as of the Date of Termination; provided that, notwithstanding the foregoing, if such termination of employment occurs within the period beginning 2 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 12 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 CIC Termination, the 12-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). 

  Notwithstanding the foregoing, it shall be a condition to the Executive’s right to receive the amounts provided for in Sections 4(a)(i), 4(a)(ii) and 4(a)(iii) 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.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 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) 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 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 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 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.

  b.This Agreement shall inure to the benefit of and be binding upon the Company and its successors and assigns.

  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: 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.

  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.Section 280G of the Code.

  i.Best Pay Provision.  In the event that any payment or benefit received or to be received by the Executive pursuant to the terms of any plan, arrangement or agreement (including any payment or benefit received in connection with a change in ownership or control or the termination of the Executive’s employment) (all such payments and benefits being hereinafter referred to as the “Total Payments”) would be subject (in whole or part) to the excise tax (the “Excise Tax”) imposed under Section 4999 of the Code, then the Total Payments shall 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 (after subtracting the 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 (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); provided, however, that this sentence shall not apply if, immediately before the change in ownership or control on which such Total Payments are contingent or otherwise relate, no stock in the Company is readily tradeable on an established securities market or otherwise (as determined  in accordance with Treasury Reg. Section 1.280G-1 Q&A 6).  Except to the extent that an alternative reduction order would result in a greater economic benefit to the Executive on an after-tax basis, the parties intend that the Total Payments shall be reduced in the following order: (w) reduction of any cash severance payments otherwise payable to the Executive that are exempt from Section 409A of the Code, (x) reduction of any other cash payments or benefits otherwise payable to the Executive that are exempt from Section 409A of the Code, but excluding any payment attributable to the acceleration of vesting or payment with respect to any equity award that is exempt from Section 409A of the Code, (y) reduction of any other payments or benefits otherwise payable to the Executive on a pro-rata basis or such other manner that complies with Section 409A of the Code, but excluding any payment attributable to the acceleration of vesting and payment with respect to any equity award that is exempt from Section 409A of the Code, and (z) reduction of any payments attributable to the acceleration of vesting or payment with respect to any equity award that is exempt from Section 409A of the Code; provided, in case of clauses (x), (y) and (z), that reduction of any payments or benefits attributable to 

   

  

   

  the acceleration of vesting of equity awards shall be first applied to equity awards with later vesting dates; provided, further, that, notwithstanding the foregoing, any such reduction shall be undertaken in a manner that complies with and does not result in the imposition of additional taxes on the Executive under Section 409A of the Code.  The foregoing reductions shall be made in a manner that results in the maximum economic benefit to the Executive on an after-tax basis and, to the extent economically equivalent payments or benefits are subject to reduction, in a pro rata manner.

  ii.Determinations. All determinations regarding the application of this Section 10(f) shall be made by an independent accounting firm or consulting group with nationally recognized standing and substantial expertise and experience in performing calculations regarding the applicability of Section 280G of the Code and the Excise Tax retained by the Company prior to the date of the applicable change in ownership or control (the “280G Firm”).  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 shall be taken into account which (x) 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, or (y) 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, (ii) 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, 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 280G Firm in accordance with the principles of Sections 280G(d)(3) and (4) of the Code.  All determinations related to the calculations to be performed pursuant to this this Section 10(f) shall be done by the 280G Firm.  The 280G Firm will be directed to submit its determination and detailed supporting calculations to both the Executive and the Company within fifteen (15) days after notification from either the Company or the Executive that the Executive may receive payments which may be “parachute payments.”  The Executive and the Company will each provide the 280G Firm access to and copies of any books, records, and documents as may be reasonably requested by the 280G Firm, and otherwise cooperate with the 280G Firm in connection with the preparation and issuance of the determinations and calculations contemplated by this Agreement.  The fees and expenses of the 280G Firm for its services in connection with the determinations and calculations contemplated by this Agreement will be borne solely by the Company.

  iii.Exception.  Notwithstanding the foregoing, if any portion of the Total Payments would not be subject to the Excise Tax if the stockholder approval requirements of Section 280G(b)(5) of the Code are satisfied, subject to the Executive’s waiver of the rights to such portion of the Total Payments above the safe harbor threshold in accordance with and to the extent required by Section 280G of the Code with respect to any portion of the Total Payments that would otherwise be subject to excise tax imposed by Section 4999 of the Code (before giving effect to any reduction in the Total Payments contemplated above), the Company shall use its reasonable best efforts to cause such payments to be submitted for such approval prior to the event giving rise to such payments.  To the extent the Company submits 

   

  

   

  any payment or benefit payable to the Executive under this Agreement or otherwise to the Company’s stockholders for approval in accordance with Treasury Reg. Section 1.280G-1 Q&A 7, the foregoing provisions under this Section 10(f) shall not apply following such submission and such payments and benefits will be treated in accordance with the results of such vote, except that any reduction in, or waiver above the safe harbor threshold of, such payments or benefits required by such vote will be applied without any application of discretion by the Executive and in the order prescribed in Section 10(f)(i).

  g.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.

  h.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.

  i.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.

  j.Amendment.  No amendment or other modification of this Agreement shall be effective unless made in writing and signed by the parties hereto.

  k.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]

   

   

   

   

  

   

   

  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/ Robert Bennett

	Name: Robert Bennett

	Title: Chief Executive Officer

	 

	 

	
"EXECUTIVE"

	 

	 

	/s/ Kevin O'Brien

	Kevin O'Brien

   

   

   

  

   

   

  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 on the date written below.

   

  		
	Date: 
	 

	 
	Name:

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