Amended and Restated EngageSmart, Inc. CVR Bonus Award Plan

As used herein, the following terms have the meanings set forth below:

“Affiliate” shall mean, with respect to any specified Person, any other Person that directly or indirectly controls, is controlled by or is under common control with such specified Person. For the purposes of this definition, the term “control,” when used with respect to any specified Person, means the power to direct or cause the direction of the management or policies of such Person, directly or indirectly, whether through the ownership of voting securities, by contract or otherwise; and the terms “controlling” and “controlled” have correlative meanings. Notwithstanding anything to the contrary set forth in this Plan, (a) no portfolio company of GA LLC or its Affiliates shall be deemed or treated as an Affiliate of the General Atlantic Shareholder, except that any such portfolio company that is directly or indirectly controlled by GA LLC or its Affiliates shall be treated as an Affiliate of the General Atlantic Shareholder solely for purposes of the definition of “Closing Class A-1 Common Shares”.

“Closing Class A-1 Common Shares” shall mean the Class A-1 Common Shares of EngageSmart, LLC owned by the General Atlantic Shareholder as of February 11, 2019 and any equity interest in the Company thereafter received in exchange for or conversion of such Class A-1 Common Shares.

“Company Offeror” shall mean (a) the Company, (b) any successor to the Company or any surviving entity resulting from a merger, consolidation or other business combination involving the Company or any wholly-owned Company Subsidiary, (c) any Company Subsidiary that is a holding company for all or substantially all of the operating assets of the Company Subsidiaries, or (d) any other entity (including the General Atlantic Shareholder) the securities of which are exchanged for Shares in anticipation of an IPO.

“Company Subsidiary” shall mean any entity of which securities or ownership interests having voting power to elect a majority of the board of directors or other persons performing similar functions are at the time directly or indirectly owned by the Company or of which the Company or a Company Subsidiary is the sole member or manager or which the Company otherwise

directly or indirectly owns or controls a majority of the partnership, limited liability company or other similar ownership interests or if the Company directly or indirectly is allocated a majority of partnership, limited liability company or other business entity gains or losses or is or directly or indirectly controls the managing director or general partner of such partnership, limited liability company or other business entity.

“CVR Amount” shall mean $70,000,000.

“CVR Distributions” shall mean any cash distributions to the General Atlantic Shareholder attributable to the Closing Class A-1 Common Shares in excess of the Performance Threshold up to a maximum of the Maximum CVR Bonus Pool.

“Exit Event” shall mean (a) the date on which the General Atlantic Shareholder sells down to one or more third parties (including by way of merger or other business combination), its direct or indirect equity investment in the Company or any successor thereto, to less than 50% of all of the then outstanding equity interests of the Company or such successor or (b) the consummation of a sale, transfer or other disposition of all or substantially all of the assets of the Company and the Company Subsidiaries, taken as a whole, to one or more third parties. For the avoidance of doubt, a merger, amalgamation, consolidation, business combination, plan of arrangement, initial public offering of equity interests of the Company or any of its Affiliates or any Company Subsidiary or other transaction involving the Company or any of its Affiliates or the Company Subsidiaries shall not in and of itself constitute an Exit Event if it does not also result in the actions set forth in clause (a) or (b) of the immediately preceding sentence.

“Forfeited CVR Bonus Amount” shall mean the amounts payable under any Award Certificate that have been forfeited by a participant from and after the Effective Date in accordance with the terms of such Award Certificate as of the date of the applicable CVR Distribution.

“GA LLC” shall mean General Atlantic LLC, a Delaware limited liability company and any successor to such entity.

“General Atlantic Shareholder” shall mean (a) General Atlantic (IC), L.P., a Delaware limited partnership and (b) any Affiliate of GA LLC that, after the Effective Date, acquires equity interests in the Company.

“IPO” shall mean an initial registered offering of equity securities of the Company or any Company Offeror to the public pursuant to an effective registration statement (other than Form S-4 or S-8 or any successor form) under the Securities Act that is underwritten by one or more internationally recognized underwriting firms and where such public offering is broadly distributed and pursuant to which one or more classes of Shares or the common stock or other equity securities of such Company Offeror are listed on The New York Stock Exchange or the Nasdaq Stock Market, either of their respective successors, or any other national securities exchange.

“Person” shall mean any individual, firm, corporation, partnership, limited liability company or other entity.

“Proceeds” shall mean all cash proceeds actually received by the General Atlantic Shareholder (net of any applicable fees, costs, expenses, discounts, commissions and similar deductions, in each case payable to a third party in connection therewith) attributable to the Closing Class A-1 Common Shares (or any other securities (excluding cash) into which any portion of such Closing Class A-1 Common Shares convert or have been exchanged) as a result of (a) dividends, (b) the sale, directly or indirectly through the sale of direct or indirect interests in the General Atlantic Shareholder (in each case, other than to an Affiliate of GA LLC), of Closing Class A-1 Common Shares (or any other securities (excluding cash) into which any portion such Closing Class A-1 Common Shares convert or have been exchanged) and (c) the sale of non-cash consideration received by the General Atlantic Shareholder as a result of the sale, directly or directly, of the General Atlantic Shareholder (in each case, other than to an Affiliate of GA LLC), of its Closing Class A-1 Common Shares (or any other securities (excluding cash) into which any portion of such Closing Class A-1 Common Shares convert or have been exchanged). Notwithstanding the foregoing, in the event of a pro-rata distribution of Shares to the limited partners of the General Atlantic Shareholder, “Proceeds” shall also include the fair market value of the Shares distributed to such limited partners, calculated in a manner consistent with the value used to determine the allocation of shares in such distribution.

“Sale Transaction” shall mean, whether in a single transaction or a series of related transactions, (a) any merger, tender offer or other business combination in which the Persons owning a majority of the voting securities of the Company prior to such transaction do not own a majority of the voting securities of the Company or the surviving Person, as applicable, immediately following the closing of such transaction or (b) the sale, transfer or other disposition of all or substantially all of the assets of the Company and the Company Subsidiaries, taken as a whole.

“Shares” shall mean any equity interests in the Company, including any equity interests in any predecessor or successor to the Company.

Except to the extent prohibited by applicable law, the Plan Administrator may allocate all or any portion of its responsibilities and powers to any one or more of its members and may delegate all or any part of its responsibilities and powers to any Person or Persons selected by it. Any such allocation or delegation may be revoked by the Plan Administrator at any time. Without limiting the generality of the foregoing, the Plan Administrator may delegate to one or more officers of the Company or any of its Affiliates the authority to act on behalf of the Plan Administrator with respect to any matter, right, obligation, or election which is the responsibility of or which is allocated to the Plan Administrator herein, and which may be so delegated as a matter of law.

The Plan Administrator shall, without the review or approval of any Person, in good faith determine: (i) the amount of any CVR Units issued under the Plan; (ii) the calculation of any amount to be paid in respect of CVR Units; and (iii) acting reasonably, any other terms and conditions attributable to the Plan. This document sets out the terms of the Plan. Details of individual awards are set out in a personalized “Award Certificate.”

CVR Unit Awards. Participants in the Plan shall be awarded “CVR Units,” which are designed as contingent value rights and are intended to provide the participant value to the extent that the General Atlantic Shareholder receives cash distributions in respect of the Closing Class A-1 Common Shares, that together with all other Proceeds received by the General Atlantic Shareholder in respect of the Closing Class A-1 Common Shares, equals $889,128,221.82 (“Performance Threshold”). CVR Units awarded hereunder shall be subject to the terms and conditions set forth in the Plan and a participant’s Award Certificate.

CVR Bonus Pools. Subject to the achievement of the Performance Threshold, a bonus pool shall be funded by an amount equal to the cumulative distributions in respect of the Closing Class A-1 Common Shares held by the General Atlantic Shareholder that are attributable to such shares pursuant to CVR Distributions up to a maximum amount as of the Effective Date of $9,469,812.41. The bonus pool described in the immediately preceding sentence shall be adjusted by reducing such amount by the Forfeited CVR Bonus Amount. The bonus pool as described in this paragraph as adjusted to reflect the Forfeited CVR Bonus Amount shall be referred to herein as the “Maximum CVR Bonus Pool”, and each individual bonus pool with respect to any payment made pursuant to CVR Distributions shall be referred to herein as a “CVR Bonus Pool.” All determinations regarding the funding of the CVR Bonus Pool and the Maximum CVR Bonus Pool shall be made in good faith by the Plan Administrator. As of the Restatement Date, the Maximum CVR Bonus Pool is $7,496,956.

Forfeiture of CVR Unit Awards. Except as set forth in the immediately following sentence and in the “Escrow/Holdback/Earnout Adjustment” below, a participant must remain continuously employed by his or her Employer on the date of any payment made pursuant to a CVR Distribution in order to be eligible to receive such payment in respect of his or her CVR Units under the Plan. A participant’s CVR Units shall be forfeited upon termination of employment or service with his or her Employer for any

reason; provided, however, that (i) if a participant’s employment or service is terminated other than for Cause, or for Good Reason (as such terms are defined in a participant’s Award Certificate), and any payment is made pursuant to a CVR Distribution within the six (6) month period immediately following the date of such termination with respect to an Exit Event that constitutes a change in control for purposes of Section 409A of the Internal Revenue Code of 1986, as amended (the “Code”), including the rules, regulations and other guidance promulgated thereunder (“Section 409A”, and such change in control, a “409A Change in Control”), then the participant shall receive the payments that he or she would have received in respect of the CVR Units under the Plan during such six (6) month period as if his or her employment or service had not terminated, and (ii) any such forfeiture shall not impair a participant’s right to payments described in the “Escrow/Holdback/Earnout Adjustment” below (including following a 409A Change in Control that occurs within the six-month period described in the preceding clause (i)).

Timing of Payouts. Payments in respect of any outstanding CVR Units shall be paid as promptly as reasonably practicable and in any event within 30 days following the occurrence of a payment made pursuant to CVR Distribution (the date of each such payment, a “Payment Date”).

Payout Amount. Except as set forth in the Plan or the applicable Award Certificate, upon a Payment Date, each participant shall be entitled to a cash payment from the Company in respect of such participant’s pro-rata portion of the applicable CVR Bonus Pool, which shall be determined by multiplying the Participation Percentage by the applicable CVR Bonus Pool. The “Participation Percentage” for a participant means the product, expressed as a percentage, obtained by multiplying (x) 100 by (y) the quotient obtained by dividing the number of CVR Units issued and outstanding to such participant, by the number of CVR Units issued and outstanding to all participants in the Plan as of immediately prior to any payment made pursuant to a CVR Distribution. The payout amount in respect of a participant’s CVR Units on any date shall be determined by the Plan Administrator in good faith.

No Contributions. Participants are not required to make any payment in order to participate in the Plan or to receive a CVR Unit award.

CVR Units subject to a CVR Unit award may be adjusted by the Plan Administrator reasonably and in good faith (but without limiting the ability of the Plan Administrator to effect any Specified Restructuring) to appropriately give effect to any corporate event or transaction involving the Company (including, but not limited to, a change in the capitalization of the Company) such as an initial registered offering of the equity securities of the Company to the public pursuant to an effective registration statement under the Securities Act where such public offering is broadly distributed and pursuant to which one or more classes of equity securities are listed on The New York Stock Exchange or the Nasdaq Stock Market or any other national securities exchange, a contribution, merger, consolidation, reorganization, recapitalization, separation, stock dividend, stock split, reverse stock split, split-up, spin-off, combination of equity securities, exchange of equity securities, dividend in kind, extraordinary cash dividend, amalgamation, or other like change in capital structure (other than regular cash dividends to stockholders of the Company), or any similar corporate event or transaction. Such adjustments may include, but are not limited to, (i) adjusting the number of CVR Unit awards or the applicable Participation Percentage; (ii) continuing or assuming such outstanding CVR Unit awards under the Plan by the Company (if it is the surviving company or its parent) or by the surviving company or its parent; (iii) substituting CVR Unit awards by the surviving company or its parent; (iv) adjusting the performance targets under outstanding CVR Unit awards immediately prior to the occurrence of such event; (v) cancelling vested CVR Unit awards in exchange for a payment in cash equal to the value of the canceled CVR Unit awards in connection with a 409A Change in Control; and (vi) cancelling out-of-the-money CVR Unit awards following a 409A Change in Control; provided that with respect to clauses (v) and (vi), the Plan Administrator must have obtained the consent set forth in the last sentence of this paragraph of this “Adjustments” section. In addition to the foregoing, notwithstanding anything to the contrary herein, the Plan Administrator may in its sole discretion determine, in connection with

a 409A Change of Control, Sale Transaction, IPO or any other similar transaction in which equity securities of the Company that were outstanding as of the Effective Date (or that were transferred in exchange for, converted from, or otherwise originated out of such equity securities) are being transferred, to cause the participants in this Plan to have their CVR Unit awards assumed by an entity treated as a partnership for tax purposes that also holds the such equity securities (the actions in this sentence, a “Specified Restructuring”). For the avoidance of doubt, the participants agree and acknowledge that in no event shall the incurrence of any tax costs or tax consequences with respect to any participant or the Company in connection with a Specified Restructuring, including the tax consequences described in the immediately following paragraph, be considered in determining whether any action taken by the Board, the Company and/or the Plan Administrator is or is not “reasonable”. Moreover, the value of such CVR Unit awards and whether the Performance Threshold is satisfied at the time of such transaction, including the value of any non- cash or escrowed or other deferred consideration, shall be determined by the Plan Administrator in good faith. Furthermore, the Plan Administrator may in good faith make reasonable adjustments to the Plan (including, without limitation, adjustments in the manner of calculating the Maximum CVR Bonus Pool and each CVR Bonus Pool) in the event of a change in circumstances affecting the Company or investments in the Company that would result in an enlargement or dilution of a Participant’s rights under the Plan from what was originally contemplated and that any other amendments or adjustments to the Plan not permitted to be made by the Board hereunder (including under this “Adjustments” section) shall require the consent of a majority of CVR Units; provided, that no amendment shall provide for disproportionate rights amongst participants. Any adjustments made pursuant to this provision of the Plan shall be determined in a manner consistent with Section 409A. Any actions by the Board, the Company and/or the Plan Administrator will be deemed for purposes of the Plan to have been “reasonable” if done with the written consent of either (x) Robert Bennett (unless he dies or becomes disabled, in which case a senior executive of the Company that holds CVRs designated by the holders of a majority of the CVR Units may provide such consent) or (y) a majority of participants (either by number of participants or number of CVR Units held).

The participants acknowledge that any restructuring or reorganization pursuant to a Specified Restructuring may result in additional administrative and organizational costs (including those resulting from the formation and maintenance of the partnership contemplated by the Specified Restructuring) to the Company (or such partnership) and material adverse tax costs to the participant and/or the Company. The participants further acknowledge that each participant shall bear any tax costs of such participant and any withholding tax obligations of the Company or its Affiliates (but excluding, for the avoidance of doubt, the employer portion of any withholding taxes, payroll taxes or similar taxes) arising as a result of a Specified Restructuring to the extent it relates to the CVR Unit award (collectively, “Restructuring Taxes”). Subject to Section 409A, the Company may offset and reduce any amounts due to the participant under the CVR Unit award, any employment arrangement (other than base salary or base wages and expense

Nothing in the Plan shall interfere with or limit in any way the right of the Employer to terminate any participant’s employment at any time, or confer upon any participant any right to continue to be employed by the Employer for any period of time.

A participant shall have no entitlement to compensation or damages in consequence of the termination or cessation of the participant’s employment or services with the Company or any Affiliate for any reason whatsoever and whether or not in breach of contract, insofar as such entitlement arises or may

arise from the participant ceasing to have CVR Units under the Plan or to be entitled to any CVR Units as a result of such termination or from the loss or diminution in value of the same. The CVR Units shall not be reinstated if the participant ceases employment with and is subsequently reinstated as an employee of the Company or any Affiliate.

The Plan and the benefits offered under the Plan are provided by the Company on an entirely discretionary basis, and the Plan creates no vested rights in participants. The Plan does not confer upon participants any benefit other than as specifically set forth in the Plan. The grant of a CVR Unit award does not entitle the participant to any future benefits under the Plan or any other plan or program of the Company or any Affiliate.

The participant shall have no right whatsoever to obtain any information about the identities of the members of the Company or its Affiliates or members of Employer (or of the size or nature of such members’ interests in the Company or any of its Affiliates).

Each participant shall covenant and agree to make such other reasonable and customary representations as requested by the Company regarding matters relevant to compliance with any applicable laws or regulations, including securities laws, as are deemed necessary by counsel to the Company.

The participants in the Plan agree that, to the fullest extent permitted by applicable legal requirements, all legal actions (whether in contract or tort) arising out of or relating in any way to this Plan or an Award Certificate, or the negotiation, execution or performance of this Plan or an Award Certificate (including any claim or cause of action based upon, arising out of or related to any representation or warranty made in or in connection with this Plan or an Award Certificate or as an inducement to agree to the terms thereof), shall be resolved exclusively by arbitration, before a single neutral arbitrator, who shall have significant experience litigating or arbitrating disputes involving the media and entertainment industry, in accordance with the rules and regulations of JAMS or its legal successor in effect at the time of initiation of the arbitration. The arbitration award in any such arbitration may be confirmed by any court of competent jurisdiction. Any such arbitration shall take place in New York, New York. Each participant and the Employer agree that they shall participate in good faith and that they shall share equally in the administrative costs and arbitrator’s fees associated with the arbitration; provided, however, that each party shall bear its own attorneys’ fees and costs associated with the arbitration. Notwithstanding the foregoing, in the event that any dispute between the participant and the Employer should result in arbitration, the prevailing party shall be entitled to recover from the other party all reasonable attorneys’ fees, costs and other expenses incurred by the prevailing party in connection with the dispute.

Each participant in the Plan waives, to the fullest extent permitted by applicable legal requirements, any right he or she may have to a trial by jury in respect of any litigation arising out of or in connection with this Plan or an Award Certificate or in any way connected with or related to or incidental to the dealings of the parties in respect of this Plan, any Award Certificate or any

AMENDMENT

AND TERMINATION:

NO ADDITIONAL

GRANTS