Document:

EX-10.21

 Exhibit 10.21 

AMERICAN WELL CORPORATION 

EMPLOYMENT AGREEMENT 

THIS EMPLOYMENT AGREEMENT (the “Agreement”) is hereby entered into as of June 18, 2020 (the “Effective
Date”) by and between American Well Corporation, a Delaware corporation (the “Company”), and Roy Schoenberg, an individual (the “Executive”) (hereinafter collectively referred to as “the
parties”). Where the context requires, references to the Company shall include the Company’s subsidiaries and affiliates. 

RECITALS 
 WHEREAS, the
Company desires to continue to employ Executive for the period provided in this Agreement, and Executive desires to accept such continued employment with the Company, subject to the terms and conditions set forth herein; 

NOW, THEREFORE, in consideration of the respective agreements of the parties contained herein, it is agreed as follows: 

1. Commencement Date; Term; Effect on Other Agreements. The employment term (the “Employment Term”) of Executive’s
employment under this Agreement shall be for the period commencing on June 18, 2020 (the “Commencement Date”) and ending on the third (3rd) anniversary of the
Commencement Date. Thereafter, the Employment Term shall extend automatically for consecutive periods of one year unless either party provides notice of non-renewal not less than ninety (90) days prior to
the end of the Employment Term as then in effect. 
 2. Employment. During the Employment Term: 

 

	 	(a)	 Subject to Section 2(d) hereof, Executive shall be employed as President and co-Chief Executive Officer of the Company and Executive shall perform the duties, undertake the responsibilities and exercise the authority customarily performed, undertaken and exercised by Executive in the past.
Executive shall report solely and directly to the board of directors of the Company (the “Board”). Executive shall continue to serve on the Board during the Employment Term and as otherwise provided in the Company’s governing
documents. 

  

	 	(b)	 Excluding periods of vacation and sick leave to which Executive is entitled and other service outside of the
Company contemplated in this Section 2(b), Executive shall devote substantially all of Executive’s professional time and attention to the business and affairs of the Company to discharge the responsibilities of
Executive hereunder. Executive may manage personal and family investments, engage in educational activities, participate in industry organizations and charitable endeavors and, with the consent of the Board (which shall not be unreasonably
withheld), serve on up to two (2) for-profit boards of directors, so long as such activities do not interfere with the performance of Executive’s responsibilities hereunder. It is understood that,
during Executive’s employment by the Company, Executive shall not engage in any activities that constitute a conflict of interest with the interests of the Company or its direct and indirect subsidiaries. 

  
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	 	(c)	 Executive shall be subject to and shall abide by each of the personnel policies applicable to senior
executives, including but not limited to any policy restricting pledging and hedging investments in Company equity by Company executives, any policy the Company adopts regarding the recovery of incentive compensation applicable if a financial metric
used to determine the amount of incentive compensation has been miscalculated, the Company is required to restate its financial statements or Executive engages in significant illegal conduct (but in the case of illegal conduct the clawback shall be
limited to the extent such illegal conduct resulted in inappropriate payment of incentive compensation) (sometimes referred to as “clawback”) and any additional clawback provisions as required by law and applicable listing rules.
This Section 2(c) shall survive the termination of the Employment Term. 

  

	 	(d)	 Executive’s position, title and duties with the Company may be adjusted following the completion of an
initial public offering of the Company’s common stock (an “IPO”), including pursuant to any modifications to the Company’s organizational or executive structure, as determined by the Board in consultation with Executive.
Any such adjustments shall not constitute Good Reason for purposes of this Agreement; provided that Executive remains in a “C-suite” level role or higher with the Company following such
adjustment. 

  

	 	(e)	 Subject to Sections 7, 8 and 9 hereof, Executive’s employment with the Company is
“at will,” such that each of Executive or the Company has the option to terminate Executive’s employment at any time, with or without advance notice, and with or without Cause or with or without Good Reason. This Agreement does not
constitute an express or implied agreement of continuing or long-term employment. 

 3. Annual Compensation. 

 

	 	(a)	 Base Salary. During the Employment Term, Executive shall be paid an annual base salary of US $650,000
(“Base Salary”). The Base Salary shall be payable in accordance with the Company’s regular payroll practices as then in effect. 

  
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	 	(b)	 Annual Bonus. Subject to the terms of the Company’s annual cash bonus program as in effect from
time to time and the provisions hereof, for each fiscal year of the Company ending during the Employment Term (commencing with the 2020 fiscal year), Executive shall be eligible to receive a target annual cash bonus of up to 150% of Base Salary
(such target bonus, as may hereafter be increased, the “Target Bonus”), with the opportunity for increased payment upon performance overachievement as determined by the Board in its discretion. Annual bonuses, if any, will be
payable after the close of the applicable fiscal year, but in any event prior to March 15 of the following calendar year. The criteria for, and attainment of, Executive’s annual bonus will be at the sole discretion of the Board following
consultation with Executive and may be based on the achievement of both corporate and personal performance objectives. 

  

	 	(c)	 Annual Review. On an annual basis during the Employment Term, the Board shall review and analyze the
then-current Base Salary and Target Bonus of Executive and determine, in its discretion, whether increases are necessary or advisable based on merit, to meet industry benchmarks or otherwise, taking into account market practice and the performance
of both the Company and Executive. The Base Salary and Target Bonus, as may be increased from time to time, shall not thereafter be decreased. 

4. Additional Compensation. 
  

	 	(a)	 Cash Award. As consideration for entering into this Agreement, Executive will receive, on the first
regular payroll date following the Commencement Date, a cash payment equal to $1,000,000 (the “Cash Award”). This amount of the Cash Award shall be inclusive of any amount payable to Executive as an over-attainment bonus in respect
of the 2019 fiscal year. 

  

	 	(b)	 2018 Options. As consideration for entering into this Agreement, the vesting terms of the non-qualified and incentive stock options granted to Executive on October 25, 2018 (the “2018 Options”) are hereby amended to provide that such options shall service-vest over a two (2)-year
period from the grant date, such that the remaining unvested options shall vest in equal quarterly installments until the options are fully vested on November 24, 2020. Executive acknowledges that such acceleration of vesting may cause all or a
portion of such incentive stock options to cease being qualified as incentive stock options under Section 422(b) of the Internal Revenue Code of 1986, as amended (the “Code”). 

 

	 	(c)	 RSU Grants. During the Employment Term, Executive shall be entitled to receive the following grants of
restricted stock units (“RSUs”) with respect to shares of the Company’s common stock (“Shares”): 

  

	 	(1)	 No later than ten (10) business days following the Commencement Date, Executive shall receive a grant of
service-vesting RSUs with respect to 325,100 Shares, which shall be granted under the terms of the Company’s 2006 Employee, Director and Consultant Stock Plan, as amended and restated (the “2006 Plan”) and have a vesting

  
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commencement date of January 1, 2019 (the “2019 RSUs”). The 2019 RSUs shall vest over a three (3)-year period, with 50% of the 2019 RSUs vesting on July 1, 2020 and the
remaining 50% vesting in equal quarterly installments thereafter; provided that, in the event of a termination of Executive’s employment, the 2019 RSUs shall be treated in accordance with Section 9 hereof.

  

	 	(2)	 Upon the earlier to occur of (i) an IPO that closes on or before December 31, 2020 (a “2020
IPO”) and (ii) the execution on or before December 31, 2020 of a definitive transaction agreement to enter into a “Corporate Transaction” (as such term is defined in Exhibit B) (a “2020 Sale”),
Executive shall be entitled to receive a grant of RSUs based on the percentage (not to exceed 1.5%) of the Company’s fully-diluted outstanding capital stock (not taking into account such grant or the 2020 IPO or 2020 Sale, as applicable)
determined in accordance with Exhibit A (the “Equity Percentage”), as follows: 

(i) RSUs granted in connection with the 2020 IPO (the “IPO RSUs”) shall be granted in the following two
traches: (A) 50% of the IPO RSUs shall be granted on or promptly following the closing date of the 2020 IPO, with an Equity Percentage based on the closing price per Share on such closing date (“Tranche 1”), and (B) 50% of
the IPO RSUs shall be granted on or promptly following the 180-day anniversary of the closing of the 2020 IPO, with an Equity Percentage based on the average of the five (5) highest closing prices per
Share during the period beginning on the date of the Company’s first earnings release following the 2020 IPO (or the 140-day anniversary of the 2020 IPO closing date, if earlier) and ending on the 180-day anniversary of the 2020 IPO closing date (“Tranche 2”), in each case subject to Executive’s continued employment through the closing date of the 2020 IPO, other than as provided in
Section 4(c)(2)(iii). The IPO RSUs shall vest and settle in Shares over the three (3)-year period from the 2020 IPO closing date, with one-third of the IPO RSUs vesting on the first
anniversary thereof and the remaining IPO RSUs vesting in equal quarterly installments thereafter; provided that, in the event of a termination of Executive’s employment, the IPO RSUs shall be treated in accordance with
Section 9 hereof. 
 (ii) RSUs granted in connection with the 2020 Sale (the “Sale
RSUs”, and together with the IPO RSUs, the “Additional RSUs”) shall be granted and immediately payable in cash on the closing date of the 2020 Sale based on the price per Share paid to the Company’s shareholders on
such closing date, subject to Executive’s continued employment through such grant date, other than as provided in Section 4(c)(2)(iii). 

  
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 (iii) The Additional RSUs shall be granted under the equity compensation
plan that the Company intends to adopt in connection with the IPO (the “IPO Plan”) or the 2006 Plan, as applicable (such plan, as amended and restated from time to time, the “Plan”), shall be subject to the terms of
the Plan and the applicable award agreement thereunder and, except as expressly set forth in this Agreement or the applicable award agreement, are intended to contain terms and conditions generally applicable to RSUs granted to similarly situated
executives of the Company. In the event that Executive’s employment is terminated by the Company without Cause or by Executive with Good Reason prior to the Tranche 1 and/or Tranche 2 grant(s) or 2020 Sale, as applicable, the Company shall
grant Executive the Additional RSUs pursuant to this Section 4(c)(2), effective as of the scheduled grant date(s) of the Tranche 1 and/or Tranche 2 grants or 2020 Sale, respectively. For the avoidance of
doubt, (i) in no event shall both the IPO RSUs and Sale RSUs be granted hereunder, (ii) if the closing of the 2020 Sale does not occur, then no Sale RSUs shall be granted or paid out under this Agreement and (iii) any IPO RSUs granted
pursuant to the immediately preceding sentence shall be vested as of grant. 
  

	 	(d)	 Ongoing Grants. Executive shall be eligible for consideration for additional equity grants during the
Employment Term in the sole discretion of the Board (the “Ongoing Grants”); provided that no such grants shall be made prior to March 1, 2021. Any Ongoing Grants shall be subject to the availability of Shares at the time
of grant and such vesting terms and conditions as may be determined by the Board in its discretion, and both the amount and type of such grants shall be based on merit, to meet industry benchmarks or otherwise, taking into account market practice
and the performance of both the Company and Executive. 

  

	 	(e)	 Corporate Transaction. All of Executive’s outstanding equity awards shall vest and be paid or
become exercisable, as applicable, in full immediately prior to a Corporate Transaction. 

 5. Share Ownership
Commitment. Executive agrees to comply with any share ownership requirements adopted by the Company applicable to Executive, which shall be on the same terms as similarly situated executives of the Company. 

6. Other Benefits. During the Employment Term: 
  

	 	(a)	 Employee Benefits. Executive shall be eligible to participate in the various benefits offered by the
Company on terms and conditions that are no less favorable than other senior executives of the Company, including the Company’s group medical and dental plans, life and disability insurance and 401(k) plan, which shall be no less favorable in
the aggregate than those benefits provided by the Company as of the date hereof. Benefits may be modified or changed from time to time at the sole discretion of the Company 

  
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(but not in a manner discriminatory against Executive), and the provision of such benefits to Executive in no way changes or impacts Executive’s status as an
at-will employee. The Company’s present benefit structure and other important information about the benefits for which Executive may be eligible are described in the Company’s benefits summary
booklet and in the Company’s employee handbook. Where a benefit is subject to a formal plan (for example, medical insurance or life insurance), eligibility to participate in and receive any particular benefit is governed solely by the
applicable plan document. 

  

	 	(b)	 Business Expenses. Upon submission of proper invoices in accordance with, and subject to, the
Company’s normal policies and procedures, Executive shall be entitled to receive prompt reimbursement of all reasonable out-of-pocket business, entertainment and
travel expenses incurred by Executive in connection with the performance of Executive’s duties hereunder. The Company shall provide for travel reimbursements materially consistent with those in effect as of the date hereof.

  

	 	(c)	 Paid Time Off. Executive shall be entitled to participate in the Company’s unlimited Personal Paid
Time Off Policy. 

 7. Termination. Executive’s employment with the Company hereunder may be terminated under
the circumstances set forth below; provided, however, that notwithstanding anything contained herein to the contrary, to the extent required by Section 409A (“Section 409A”) of the Code,
Executive shall not be considered to have terminated employment with the Company for purposes of this Agreement until Executive would be considered to have incurred a “separation from service” from the Company within the meaning of
Section 409A. 
  

	 	(a)	 Death. Executive’s employment shall be terminated as of the date of Executive’s death and
Executive’s beneficiaries shall be entitled to the benefits provided in Section 9(b) hereof. 

  

	 	(b)	 Disability. The Company may terminate Executive’s employment, on written notice to Executive after
having established Executive’s Disability and while Executive remains Disabled, and Executive shall be entitled to the benefits provided in Section 9(b) hereof. For purposes of this Agreement,
“Disability” shall have the meaning assigned to such term in the Plan. 

  

	 	(c)	 Cause. The Company may terminate Executive’s employment for Cause (as defined in Exhibit B)
effective as of the date of the Notice of Termination (as defined in Section 8 hereof) and Executive shall be entitled to the benefits provided in Section 9(a) hereof. 

  
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	 	(d)	 Without Cause. The Company may terminate Executive’s employment without Cause and Executive shall
be entitled to the benefits provided in Section 9(c) hereof. 

  

	 	(e)	 Good Reason. Executive may terminate Executive’s employment with Good Reason (as defined in
Exhibit B), subject to this Section 7(e) and Executive shall be entitled to the benefits provided in Section 9(c) hereof. 

 

	 	(f)	 Without Good Reason. Executive may voluntarily terminate Executive’s employment without Good Reason
by delivering to the Company a Notice of Termination not less than thirty (30) days prior to the termination of Executive’s employment and the Company shall have the option of terminating Executive’s duties and responsibilities prior
to the expiration of such thirty (30) day notice period (in which case Executive shall not receive any payment of Executive’s salary or other compensation for the balance of such thirty (30) day period), and Executive shall be
entitled to the benefits provided in Section 9(a) hereof through the last day of such notice period. 

  

	 	(g)	 Retirement. Executive may terminate Executive’s employment upon Executive’s retirement in
accordance with the terms of a retirement plan or policy of the Company approved by the Board and applicable to Executive (a “Company Retirement Plan”), and Executive shall be entitled to the benefits provided in
Section 9(d) hereof. 

  

	 	(h)	 Notice of Non-Renewal. Executive’s employment shall
terminate upon expiration of the Employment Term as then in effect following timely provision by either party of notice of non-renewal in accordance with Section 1 hereof, and
Executive shall be entitled to the benefits provided in Section 9(e) hereof 

 8. Notice of
Termination. Any purported termination by Executive shall be communicated by written Notice of Termination to the Company. For purposes of this Agreement, a “Notice of Termination” shall mean a notice which indicates a
termination date, the specific termination provision in this Agreement relied upon and sets forth in reasonable detail the facts and circumstances claimed to provide a basis for termination of Executive’s employment under the provision so
indicated. For purposes of this Agreement, no such purported termination of Executive’s employment hereunder shall be effective without such Notice of Termination (unless waived by the party entitled to receive such notice); provided
that the Company may not challenge a Good Reason termination based upon a lack of “reasonable detail” regarding the basis for termination of Executive’s employment as long as Executive otherwise meets the notice requirements set forth
in Section 7(e) hereof. 
 9. Compensation Upon Termination. Upon termination of
Executive’s employment during the Employment Term, Executive shall be entitled to the following benefits; provided, however, that any such benefits to which Executive is hereunder entitled shall be offset by those benefits that
Executive receives, if any, under applicable law or otherwise: 

  
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	 	(a)	 Termination by the Company for Cause or by Executive Without Good Reason. If
Executive’s employment is terminated by the Company for Cause or by Executive without Good Reason, the Company shall pay Executive all amounts earned or accrued hereunder through the termination date, including: 

 

	 	(1)	 reimbursement for reasonable and necessary expenses incurred by Executive on behalf of the Company for the
period ending on the termination date, pursuant to the procedures of the Company’s applicable policies; 

  

	 	(2)	 any previous compensation which Executive has previously deferred (including any interest earned or credited
thereon), in accordance with the terms and conditions of the applicable deferred compensation plans or arrangements then in effect; 

  

	 	(3)	 equity and incentive awards, to the extent previously vested, shall be paid or delivered to Executive in
accordance with the terms of such awards; 

  

	 	(4)	 any amount or benefit as provided under any benefit plan or program, and any accrued, but unpaid vacation (the
foregoing items in clauses (1) through (4) being collectively referred to as the “Accrued Compensation”); and 

  

	 	(5)	 in the case of Executive’s resignation without Good Reason, for each unvested equity award held by
Executive at the time of termination that is a 2018 Option, 2019 RSU or an IPO RSU, such award shall be eligible to continue to vest in accordance with the vesting schedule provided by the terms of the applicable award agreement (provided
that any such award that is not exempt from Section 409A must vest and be paid out on the scheduled payment dates provided under the applicable award agreement). 

 

	 	(b)	 Termination by the Company for Disability or Death. If Executive’s employment is terminated by the
Company for Disability or by reason of Executive’s death, then, subject to Section 16(e) hereof, Executive shall be entitled to the benefits provided in this Section 9(b).

  

	 	(1)	 The Company shall pay Executive (or Executive’s beneficiaries, as applicable) the Accrued Compensation;

  

	 	(2)	 The Company shall pay to Executive (or Executive’s beneficiaries, as applicable) within sixty
(60) days following the termination date, any bonus earned but unpaid in respect of any fiscal year preceding the termination date; 

  
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	 	(3)	 The Company shall pay to Executive (or Executive’s beneficiaries, as applicable) a pro rata bonus for the
year in which Executive’s employment terminates, in an amount equal to the product of (x) the quotient of the number of days Executive was employed in the applicable year, divided by 365 and (y) Executive’s then-current Target
Bonus; and 

  

	 	(4)	 Each unvested equity award held by Executive at the time of termination shall be treated as follows:

 (i) for each award that is a 2018 Option, 2019 RSU, an IPO RSU or an Ongoing Grant, such award shall
vest in full (with any performance goals applicable to an Ongoing Grant treated as achieved at target) and all outstanding stock options shall remain exercisable for their full term; and 

(ii) each other award shall be governed by the terms of the applicable award agreement. 

 

	 	(c)	 Termination by the Company Without Cause or by Executive for Good Reason. If
Executive’s employment by the Company shall be terminated by the Company without Cause or by Executive for Good Reason, then, subject to Section 16(e) hereof, Executive shall be entitled to the benefits provided
in this Section 9(c). 

  

	 	(1)	 The Company shall pay to Executive any Accrued Compensation; 

 

	 	(2)	 The Company shall pay to Executive any bonus earned but unpaid in respect of any fiscal year preceding the
termination date within sixty (60) days following the termination date; 

  

	 	(3)	 The Company shall pay to Executive a pro rata bonus for the year in which Executive’s employment
terminates, in an amount equal to the product of (x) the quotient of the number of days Executive was employed in the applicable year, divided by 365 and (y) the bonus Executive would have earned for such year had he remained employed
through year-end, within the time period set forth in Section 3(b); 

  

	 	(4)	 The Company shall pay Executive as severance pay, in lieu of any further compensation (except as provided in
this Section 9(c)) for the periods subsequent to the termination date, an amount in cash, equal to three (3) times Executive’s then-current Base Salary, paid in equal installments on the Company’s regular
payroll dates during the thirty-six (36) month period following the date on which Executive executes a release in accordance with Section 16(e) hereof (the “Severance
Period”); 

  
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	 	(5)	 Each unvested equity award held by Executive at the time of termination shall be treated as follows:

 (i) for each award that is a 2018 Option, 2019 RSU, an IPO RSU or an Ongoing Grant, such award shall
vest in full (with any performance goals applicable to an Ongoing Grant treated as achieved at target) and all outstanding stock options shall remain exercisable for their full term; and 

(ii) each other award shall be governed by the terms of the applicable award agreement. 

 

	 	(6)	 If Executive is participating in the Company’s group health insurance plans on the effective date of
termination, and Executive timely elects and remains eligible for continued coverage under the Consolidated Omnibus Budget Reconciliation Act (“COBRA”), or, if applicable, state or local insurance laws, the Company shall pay that
portion of Executive’s premiums that the Company was paying prior to the effective date of termination for the Severance Period and, if necessary due to COBRA restrictions, provide alternative coverage for any period beyond the COBRA
continuation period if Executive is not receiving comparable coverage from a subsequent employer. 

  

	 	(d)	 Termination by Executive due to Executive’s Retirement. If Executive terminates
Executive’s employment upon Executive’s retirement pursuant to a Company Retirement Plan, then, subject to Section 16(e) hereof, Executive shall be entitled to the benefits provided in this
Section 9(d). 

  

	 	(1)	 The Company shall pay to Executive any Accrued Compensation; and 

 

	 	(2)	 Each unvested equity award held by Executive at the time of termination shall be treated as follows:

 (i) for each award that is a 2018 Option, 2019 RSU, an IPO RSU or an Ongoing Grant, such award shall be
eligible to continue to vest in accordance with the vesting schedule provided by the terms of the applicable award agreement (provided that any such award that is not exempt from Section 409A must vest and be paid out on the scheduled
payment dates provided under the applicable award agreement); and 
 (ii) each other award shall be governed by the terms of
the applicable award agreement. 

  
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	 	(e)	 Expiration of Employment Term Upon Notice of
Non-Renewal. If Executive’s employment terminates upon expiration of the Employment Term as then in effect following timely provision by either party of notice of
non-renewal in accordance with Section 1 hereof, then, subject to Section 16(e) hereof, Executive shall be entitled to the benefits provided in this
Section 9(e). 

  

	 	(1)	 The Company shall pay to Executive any Accrued Compensation; and 

 

	 	(2)	 Each unvested equity award held by Executive at the time of termination shall be governed by the terms of the
applicable award agreement; provided that, in the event the Company provides such notice of non-renewal, all unvested IPO RSUs shall vest upon Executive’s termination of employment.

  

	 	(f)	 Executive shall not be required to mitigate the amount of any payment provided for under this
Section 9 by seeking other employment or otherwise and no such payment shall be offset or reduced by the amount of any compensation or benefits provided to Executive in any subsequent employment. 

10. Section 409A. This Agreement is intended to comply with, or otherwise be exempt from, Section 409A. The Company shall undertake
to administer, interpret and construe this Agreement, to the extent reasonably practicable, in a manner that does not result in the imposition on Executive of any additional tax, penalty or interest under Section 409A. If the Company determines
in good faith that any provision of this Agreement would cause Executive to incur an additional tax, penalty or interest under Section 409A, the Company and Executive shall use reasonable efforts to reform such provision, if possible, in a
mutually agreeable fashion to maintain to the maximum extent practicable the original intent of the applicable provision without violating the provisions of Section 409A. If a payment obligation under this Agreement arises on account of
Executive’s separation from service while Executive is a “specified employee” (as defined under Section 409A), then any payment that constitutes “deferred compensation” (as defined under Treasury Regulation Section 1.409A-1(b)(1), after giving effect to the exemptions in Treasury Regulation Sections 1.409A-1(b)(3) through (b)(12)) that is scheduled to be paid within six
(6) months after such separation from service shall accrue without interest and shall be paid within fifteen (15) days after the end of the six (6) month period beginning on the date of such separation from service or, if earlier,
within fifteen (15) days after the appointment of the personal representative or executor of Executive’s estate following Executive’s death. Notwithstanding the foregoing, nothing in this Agreement or otherwise is intended to, nor
does it, guarantee that the payments and benefits under this Agreement will not be subject to any additional tax or other adverse tax consequences under Section 409A or any similar state or local tax law. For purposes of Section 409A, any
series of installment payments under this Agreement shall be treated as a right to a series of separate payments. 

  
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 11. Employee Protection. Nothing in this Agreement or otherwise limits
Executive’s ability to communicate directly with and provide information, including documents, not otherwise protected from disclosure by any applicable law or privilege to the Securities and Exchange Commission (the “SEC”),
any other federal, state or local governmental agency or commission (“Government Agency”) or self-regulatory organization regarding possible legal violations, without disclosure to the Company. The Company may not retaliate
against Executive for any of these activities, and nothing in this Agreement or otherwise requires Executive to waive any monetary award or other payment that Executive might become entitled to from the SEC or any other Government Agency or
self-regulatory organization. 
 12. Records and Confidential Data. 

 

	 	(a)	 Executive acknowledges that in connection with the performance of Executive’s duties during the Employment
Term, the Company will make available to Executive, or Executive will have access to, certain Confidential Information (as defined below) of the Company and its subsidiaries. Executive acknowledges and agrees that any and all Confidential
Information disclosed to, or learned or obtained by, Executive during the course of Executive’s employment by the Company or otherwise, whether developed by Executive alone or in conjunction with others or otherwise, shall be and is the sole
and exclusive property of the Company and its subsidiaries and Executive hereby assigns to the Company any and all right, title and interest Executive may have or acquire in and to such Confidential Information. 

 

	 	(b)	 Except as provided in Section 11 hereof, the Confidential Information will be kept
confidential by Executive, will not be used in any manner which is detrimental to the Company, will not be used other than in connection with Executive’s discharge of Executive’s duties hereunder, and will be safeguarded by Executive from
unauthorized disclosure. Executive acknowledges and agrees that the confidentiality restrictions set forth herein shall apply to any and all Confidential Information disclosed to, or learned or obtained by, Executive, whether before, on or after the
date hereof. For the avoidance of doubt, nothing in this Section 12(b) shall prevent Executive from (i) complying with a valid legal requirement (whether by oral questions, interrogatories, requests for
information or documents, subpoena, civil or criminal investigative demand or similar process) to disclose any Confidential Information, (ii) using Confidential Information as reasonably necessary in connection with arbitration or litigation
between Executive and the Company or any of its affiliates or (iii) exercising any legally protected whistleblower rights (including under Rule 21F under the Securities Exchange Act of 1934, as amended) as set forth in
Section 11. 

  
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	 	(c)	 Following the termination of Executive’s employment hereunder, as soon as possible after the
Company’s written request, Executive will return to the Company all written Confidential Information which has been provided to Executive and Executive will return or destroy (or cooperate with any reasonable Company requested process to return
or destroy) all copies of any analyses, compilations, studies or other documents (including any email or other electronic correspondence) prepared by Executive or for Executive’s use containing or reflecting any Confidential Information, except
as provided in Section 11. Within five (5) business days of the receipt of such request by Executive, Executive shall, upon written request of the Company, deliver to the Company a document certifying that such written
Confidential Information has been returned or destroyed in accordance with this Section 12(c). 

  

	 	(d)	 For the purposes of this Agreement, “Confidential Information” shall mean all confidential and
proprietary information of the Company and its subsidiaries, including, without limitation, information derived from reports, investigations, experiments, research, work in progress, drawings, designs, plans, proposals, codes, marketing and sales
programs, client lists, client mailing lists, supplier lists, financial projections, cost summaries, pricing formula, marketing studies relating to prospective business opportunities and all other know-how,
trade secrets, inventions, concepts, ideas, materials, or information developed, prepared or performed for or by the Company or its subsidiaries (in each case, including any email or other electronic correspondence). For purposes of this Agreement,
the Confidential Information shall not include and Executive’s obligations shall not extend to information that Executive can demonstrate with competent evidence is (i) generally available to the public without any action or involvement by
Executive or (ii) independently obtained by Executive from a third party on a non-confidential and authorized basis. Notwithstanding anything in this Section 12 to the contrary,
Executive may disclose Confidential Information: (1) as set forth in Section 11; and (2) to the extent it is required to be disclosed by law or pursuant to judicial process or administrative subpoena. To the
extent that Confidential Information is required to be disclosed by law, governmental investigation or pursuant to judicial process or administrative subpoena, Executive shall, to the extent legally permitted, first give written notice to the
Company and reasonably cooperate with the Company (at the Company’s expense) to obtain a protective order or other measures preserving the confidential treatment of such Confidential Information and requiring that the information or documents
so disclosed be used only for the purposes required by law, governmental investigation or pursuant to judicial process or administrative subpoena, except as provided in Section 11 and subject to
Section 12(e). 

  

	 	(e)	 Notwithstanding anything in this Agreement to the contrary, pursuant to the Defend Trade Secrets Act of 2016,
the parties hereto acknowledge and agree that Executive shall not have criminal or civil liability under any federal or state trade secret law for the disclosure of a trade secret that (A) is made (i) in confidence to a federal, state, or
local government official, 

  
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either directly or indirectly, or to an attorney and (ii) 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. In addition and without limiting the preceding sentence, if Executive files a lawsuit for retaliation by the Company for reporting a suspected violation of law,
Executive may disclose the trade secret to Executive’s attorney and may use the trade secret information in the court proceeding, if Executive (X) files any document containing the trade secret under seal and (Y) does not disclose the
trade secret, except pursuant to court order. 

  

	 	(f)	 In connection with Executive’s employment with the Company, Executive will not use any confidential or
proprietary information Executive may have obtained in connection with employment with any prior employer. 

  

	 	(g)	 Executive’s obligations under this Section 12 shall survive the termination of
the Employment Term. 

 13. Covenant Not to Solicit and Not to Compete;
Non-Disparagement. 
  

	 	(a)	 Covenants Not to Solicit or to Interfere. To protect the Confidential Information and other trade
secrets of the Company and its subsidiaries, Executive agrees, during the Employment Term and for a period of twenty-four (24) months after Executive’s cessation of employment with the Company, not to solicit, hire or participate in or
assist in any way in the solicitation or hire of any employees of the Company or any of its subsidiaries (or any person who was an employee of the Company or any of its subsidiaries during the six-month period
preceding such action) in any country. For purposes of this covenant, “solicit” or “solicitation” means directly or indirectly influencing or attempting to influence employees of the Company or any of its
subsidiaries to become employed with any other person, partnership, firm, corporation or other entity. Executive shall not violate this Section 13(a) by providing a personal reference or by a general advertisement
for employees not directly or indirectly targeted at employees of the Company or its subsidiaries. 

 In addition, to
protect the Confidential Information and other trade secrets of the Company and its subsidiaries, Executive agrees, during the Employment Term and for a period of twenty-four (24) months after Executive’s cessation of employment with the
Company, not to (x) solicit any client or customer to receive services or to purchase any good or services in competition (through a Prohibited Activity) with those provided by the Company or any of its subsidiaries or (y) interfere or
attempt to interfere in any material respect with the relationship between the Company or any of its subsidiaries on one hand and any client, customer, supplier, investor, financing source or capital market intermediary on the other hand,

  
 14 

	 	
in any country. For purposes of this covenant, “solicit” or “solicitation” means directly or indirectly influencing or attempting to influence clients or
customers of the Company or any of its subsidiaries to accept the services or goods of any other person, partnership, firm, corporation or other entity in competition (through a Prohibited Activity) with those provided by the Company or any of its
subsidiaries. 

 Executive agrees that the covenants contained in this Section 13(a) are reasonable
and desirable to protect the Confidential Information of the Company and its subsidiaries; provided that solicitation through general advertising or the provision of references shall not constitute a breach of such obligations. 

 

	 	(b)	 Covenant Not to Compete. To protect the Confidential Information and other trade secrets of the Company
and its subsidiaries, and in specific consideration for a cash payment of $1,000, Executive agrees, to the maximum extent permitted by applicable law, not to become involved with any entity that directly or indirectly engages in Prohibited
Activities (as defined below) in any country in which the Company or any of its subsidiaries conducts such business, or plans to conduct such business during the Employment Term, during the period commencing with the Employment Term and ending
(i) twelve (12) months after Executive’s cessation of employment with the Company pursuant to Sections 7(b), 7(c), 7(f), 7(g) or 7(h), or (ii) twenty-four (24) months after
Executive’s cessation of employment with the Company pursuant to Sections 7(d) or 7(e) hereof. For the purposes of this Agreement, the term “Prohibited Activities” means directly or indirectly owning any
interest in, managing, participating in (whether as an employee, director, officer, consultant, partner, member, manager, representative or agent), consulting with or rendering services to any entity (including, without limitation, Doctor On Demand,
MDLive, Teladoc, Epic Systems, Cerner or Zoom) in (A) the telehealth industry or (B) digital healthcare, that, in the case of clause (B), performs or plans to perform any of the services or manufactures or sells or plans to manufacture or
sell any of the products planned, provided or offered by the Company or any of its subsidiaries or any products or services designed to perform the same function or achieve the same results as the products or services planned, provided or offered by
the Company or any of its subsidiaries or performs or plans to perform any other services and/or engages or plans to engage in the development, production, manufacture, distribution or sale of any product similar to any planned or actual services
performed or products developed, produced, manufactured, distributed or sold by the Company or any of its subsidiaries during the term of Executive’s employment with the Company and its subsidiaries, including, without limitation, any business
activity that directly or indirectly provides the research, development, manufacture, marketing, selling or servicing of systems facilitating consumer communications with professional service

  
 15 

	 	
providers in the digital healthcare field; provided that (i) Prohibited Activities shall not mean Executive’s investment in securities of a publicly-traded company (or a non-publicly traded entity through a passive investment) equal to less than five percent (5%) of such company’s outstanding voting securities, (ii) Prohibited Activities following cessation of
Executive’s employment shall not include businesses of the Company or its subsidiaries which are reasonably projected, as of the termination date, to represent less than 5% of the consolidated revenues of the Company and its subsidiaries taken
as a whole following the termination date, and (iii) Executive shall be permitted to provide services to an entity that has a unit, division, subsidiary or affiliate engaging in a Prohibited Activity so long as Executive does not provide
services, directly or indirectly, to such unit, division, subsidiary or affiliate engaging in the Prohibited Activity. Executive agrees that the covenants contained in this Section 13(b) are reasonable and desirable
to protect the Confidential Information of the Company and its subsidiaries. Any reference to plans or planned activity in this paragraph shall be limited to plans or planned activities that are based upon material demonstrable actions. Following
Executive’s cessation of employment, the prohibitions in this paragraph shall be limited to activities and planned activities (including locations) as of the date of Executive’s termination of employment. 

 

	 	(c)	 Non-Disparagement. Executive agrees not to make written or oral
statements about the Company, its subsidiaries or affiliates, or its directors, executive officers or non-executive officer employees that are negative or disparaging, except as provided in
Section 11 hereof or in the ordinary course of normal employment communications or personnel performance reviews when making such statements is reasonable and appropriate. The Company, as represented by its directors and
executive officers, shall not make written or oral statements about Executive that are negative or disparaging other than in the ordinary course of normal employment communications or personnel performance reviews when making such statements is
reasonable and appropriate. Notwithstanding the foregoing, nothing in this Agreement or otherwise shall preclude Executive, the Company, its subsidiaries and affiliates, and the Company’s directors and executive officers from communicating or
testifying truthfully to the extent required by law to any federal, state, provincial or local governmental agency or in response to a subpoena to testify issued by a court of competent jurisdiction or in connection with any litigation or
arbitration between Executive and the Company or any of its affiliates or any of its directors, executive officers or non-executive officer employees. Either party may make truthful statements to the extent
reasonably necessary to correct any inaccurate public statements made by the other party (including executives or directors of the Company) or in the normal course of permitted competitive actions. 

  
 16 

	 	(d)	 It is the intent and desire of Executive and the Company that the restrictive provisions of this
Section 13 be enforced to the fullest extent permissible under the laws and public policies as applied in each jurisdiction in which enforcement is sought. If any particular provision of this
Section 13 shall be determined to be invalid or unenforceable, such covenant shall be amended, without any action on the part of either party hereto, to delete therefrom the portion so determined to be invalid or
unenforceable, such deletion to apply only with respect to the operation of such covenant in the particular jurisdiction in which such adjudication is made. 

  

	 	(e)	 Executive’s obligations under this Section 13 shall be in full satisfaction of
Executive’s services for the Company and its affiliates from the date of his commencement of employment with the Company and shall survive the termination of the Employment Term. 

14. Remedies for Breach of Obligations under Sections 12 or 13 hereof. Executive acknowledges that the Company will suffer
irreparable injury, not readily susceptible of valuation in monetary damages, if Executive breaches Executive’s obligations under Sections 12 or 13 hereof. Accordingly, Executive agrees that the Company will be entitled, in
addition to any other available remedies, to seek injunctive relief against any breach or prospective breach by Executive of Executive’s obligations under Sections 12 or 13 hereof. Executive agrees that process in any or
all of those actions or proceedings may be served by registered mail, addressed to the last address provided by Executive to the Company, or in any other manner authorized by law. This Section 14 shall survive the
termination of the Employment Term. 
 15. Cooperation. 
  

	 	(a)	 Following Executive’s termination of employment for any reason for a period of thirty-six (36) months following such termination, except as provided in Section 11 hereof, Executive agrees to make Executive reasonably available at the request of the Company to
cooperate with the Company and its affiliates in matters that materially concern: (i) requests for information about the services Executive provided to the Company and its affiliates during Executive’s employment with the Company and its
affiliates, (ii) the defense or prosecution of any claims or actions now in existence or which may be brought in the future against or on behalf of the Company and its affiliates which relate to events or occurrences that transpired while
Executive was employed the Company and its affiliates and as to which Executive has, or would reasonably be expected to have, personal experience, knowledge or information or (iii) any investigation or review by any federal, state or local
regulatory, quasi-regulatory or self-governing authority (including, without limitation, the US Department of Justice, the US Federal Trade Commission or the SEC) as any such investigation or review relates to events or occurrences that transpired
while Executive was employed by the Company and its affiliates. Executive’s cooperation shall include: (A) making Executive reasonably available to 

  
 17 

	 	
meet and speak with officers or employees of the Company, the Company’s counsel or any third-parties at the reasonable request of the Company at times and locations to be determined by the
Company reasonably and in good faith, taking into account the Company’s business and Executive’s business and personal needs (the “Company Cooperation”) and (B) giving accurate and truthful information at any
interviews and accurate and truthful testimony in any legal proceedings or actions (the “Witness Cooperation”). Nothing in this Section 15(a) shall be construed to limit in any way any rights
Executive may have at applicable law not to provide testimony with regard to specific matters. Unless required by law or legal process, Executive will not knowingly or intentionally furnish information to or cooperate with any non-governmental entity (other than the Company) in connection with any potential or pending proceeding or legal action involving matters arising during Executive’s employment with the Company and its
affiliates, except as provided in Section 11. In addition, at the request of the Company, Executive shall be required to complete a directors’ and officers’ questionnaire to facilitate the Company’s
preparation of any filings and reports with the SEC. 

  

	 	(b)	 Executive shall not be entitled to any payments in addition to those otherwise set forth in this Agreement in
respect of any Company Cooperation or Witness Cooperation, regardless of when provided. The Company will reimburse Executive for any reasonable, out-of-pocket travel,
hotel and meal expenses incurred in connection with Executive’s performance of obligations pursuant to this Section 15 for which Executive has obtained prior approval (which shall not be unreasonably withheld) from the
Company, and which shall be at levels consistent with Executive’s travel while employed as co-Chief Executive Officer. The Company shall also reimburse Executive for reasonable legal fees incurred in
connection with Executive’s cooperation if Executive reasonably believes that separate independent counsel is appropriate. Executive shall not be required to cooperate against his own legal interests. 

 

	 	(c)	 Nothing in this Agreement or any other agreement by and between the parties is intended to or shall preclude or
in any way limit or restrict Executive from providing accurate and truthful testimony or information to any governmental agency. 

  

	 	(d)	 This Section 15 shall survive the termination of the Employment Term.

 16. Miscellaneous. 
  

	 	(a)	 Successors and Assigns. 

 

	 	(1)	 This Agreement shall be binding upon and shall inure to the benefit of the Company, its successors and
permitted assigns. The Company may not assign or delegate any rights or obligations hereunder except to a 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, as applicable. The term “the Company” as used herein shall mean a corporation or other entity acquiring all or substantially all the assets and business of the Company, as the case may be, (including this
Agreement) whether by operation of law or otherwise. 

  
 18 

	 	(2)	 Neither this Agreement nor any right or interest hereunder shall be assignable or transferable by Executive,
Executive’s beneficiaries or legal representatives, except by will or by the, laws of descent and distribution. 

  

	 	(3)	 This Agreement shall inure to the benefit of and be enforceable by Executive’s legal personal
representatives, and by Executive’s beneficiaries in the event of his death. 

  

	 	(b)	 Notice. For the purposes of this Agreement, notices and all other communications provided for in the
Agreement (including the Notice of Termination) shall be in writing and shall be deemed to have been duly given when personally delivered or sent by Certified mail, return receipt requested, postage prepaid, addressed to the respective addresses
last given by each party to each other party; provided that all notices to the Company shall be directed to the attention of the General Counsel of the Company. All notices and communications shall be deemed to have been received on the date
of delivery thereof or on the third business day after the mailing thereof, except that notice of change of address shall be effective only upon receipt. 

  

	 	(c)	 Indemnity Agreement. The Company agrees to indemnify and hold Executive harmless to the fullest extent
permitted by applicable law for actions taken as a director or officer of the Company, pursuant to the terms of the Indemnification Agreement previously entered into between the Company and Executive. In connection therewith, Executive shall be
entitled to the protection of any insurance policies which the Company elects to maintain generally for the benefit of the Company’s directors and officers, against all costs, charges and expenses whatsoever incurred or sustained by Executive
in connection with any action, suit or proceeding to which Executive may be made a party by reason of Executive’s being or having been a director, officer or employee of the Company. This provision shall survive any termination of the
Employment Term. 

  

	 	(d)	 Withholding. The Company shall be entitled to withhold the amount, if any, of all taxes of any
applicable jurisdiction required to be withheld by an employer with respect to any amount paid to Executive hereunder. The Company, in its sole and absolute discretion, shall make all determinations as to whether it is obligated to withhold any
taxes hereunder and the amount hereof. 

  
 19 

	 	(e)	 Release of Claims. The termination benefits described in Section 4(c)(2)(iii)
and Sections 9(b), 9(c), 9(d) and 9(e) hereof (the “Total Payments”) shall be conditioned on Executive delivering to the Company, and failing to revoke, a signed release of claims reasonably
acceptable to the Company within fifty (50) days following Executive’s termination date, which release shall be a general release of claims against the Company and associated individuals and entities, including customary exceptions.
Notwithstanding any provision of this Agreement to the contrary, in no event shall the timing of Executive’s execution of the release, directly or indirectly, result in Executive designating the calendar year of payment, and, to the extent
required by Section 409A, if a payment that is subject to execution of the release could be made in more than one taxable year, payment shall be made in the later taxable year. Where applicable, references to Executive in this
Section 16(e) shall refer to Executive’s representative or estate. 

  

	 	(f)	 Parachute Payments. To the extent consistent with applicable law, the payment of any amounts or the
provision of any benefits under this Agreement or any other agreement including, without limitation, the Total Payments, will be reduced or adjusted to avoid triggering the excise tax (the “Excise Tax”) imposed by Section 4999
of the Code (the “Required Reduction”), if such adjustment would result in the provision of a greater total benefit, on a net after-tax basis (after taking into account any applicable federal,
state and local income and employment taxes and the Excise Tax), to Executive. In the case of a reduction in the Total Payments, the Total Payments will be reduced in the following order: (i) by reducing any cash payments to be made to
Executive (excluding any cash payment with respect to the acceleration of equity-based compensation); (ii) by canceling the acceleration of vesting of any outstanding equity-based compensation awards; and (iii) by reducing any other non-cash benefits provided to Executive. In the case of the reductions to be made pursuant to each of the above-mentioned clauses, the payment and/or benefit amounts to be reduced, and the acceleration of vesting to
be cancelled, shall be reduced or cancelled in the inverse order of their originally scheduled dates of payment or vesting, as applicable, and shall be so reduced: (x) only to the extent that the payment and/or benefit otherwise to be paid, or
the vesting of the award that otherwise would be accelerated, would be treated as a “parachute payment” within the meaning of Code Section 280G(b)(2)(A); and (y) only to the extent necessary to achieve the Required Reduction. All
determinations made under this Section 16(f) (as well as with respect to any payments provided to any other “disqualified individual” of the Company within the meaning of Section 280G(c) of the Code) shall be
made by a 

  
 20 

	 	
nationally recognized accounting firm as mutually agreed between the Company and Executive (the “Accounting Firm”) which shall provide detailed supporting calculations to
Executive and the Company. All fees and expenses of the Accounting Firm shall be borne by the Company. All determinations by the Accounting Firm shall be binding on Executive and the Company absent manifest error. Notwithstanding the foregoing, if
prior to a change in ownership or effective control of the Company (as described in Section 280G of the Code and the regulations and guidance promulgated thereunder, no stock of the Company is readily tradable on an established securities
market and the Accounting Firm determines that the Excise Tax would be imposed upon the Total Payments (and any other payments) then, subject to Executive’s execution of a written agreement providing that Executive will waive any portion of the
Total Payments (and any other payments) that would otherwise cause such payments to be subject to the Excise Tax, the Company agrees to use commercially reasonable efforts to submit to the Company’s shareholders for approval, in a manner that
satisfies Section 280G(b)(5)(B) of the Code, Executive’s conditional right to receive the portion of the Total Payments (and other payments) otherwise subject to the waiver agreement. 

 

	 	(g)	 Modification. 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 Executive and the 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 the other party shall be deemed a waiver of similar or dissimilar provisions or conditions at the same or at any prior or subsequent time. No agreement or representations, oral or otherwise, express or implied, with respect to the
subject matter hereof have been made by any party which are not expressly set forth in this Agreement. 

  

	 	(h)	 Arbitration. If any dispute arises under this Agreement or otherwise which cannot be resolved by mutual
discussion between the parties, then the Company and Executive each agree to resolve that dispute by binding arbitration before an arbitrator experienced in employment law. Said arbitration will be conducted in accordance with the rules applicable
to employment disputes of the Judicial Arbitration and Mediation Services (“JAMS”) and the law applicable to the claim. The parties shall have thirty (30) calendar days after notice of such arbitration has been given to attempt
to agree on the selection of an arbitrator from JAMS. In the event the parties are unable to agree in such time, JAMS will provide a list of five (5) available arbitrators and an arbitrator will be selected from such five member panel provided
by JAMS by the parties alternately striking out one name of a potential arbitrator until only one name remains. The party entitled to strike an arbitrator first shall be selected by a toss of a coin. The parties agree that this agreement to
arbitrate includes any such disputes that 

  
 21 

	 	
the Company may have against Executive, or Executive may have against the Company and/or its related entities and/or employees, arising out of or relating to this Agreement, or Executive’s
employment or Executive’s termination, including any claims of discrimination or harassment in violation of applicable law and any other aspect of Executive’s compensation, employment, or Executive’s termination. The parties further
agree that arbitration as provided for in this Section 16(h) is the exclusive and binding remedy for any such dispute and will be used instead of any court action, which is hereby expressly waived, except for any
request by any party for temporary, preliminary or permanent injunctive relief pending arbitration in accordance with applicable law or for breaches by Executive of Executive’s obligations under Sections 12, 13 or 15
hereof. The parties agree that the seat of the arbitration shall be Boston, Massachusetts. The Company shall pay the cost of any arbitration brought pursuant to this paragraph, excluding, however, the cost of representation of Executive, unless such
cost is awarded in accordance with law or otherwise awarded by the arbitrators. Neither party nor an arbitrator may disclose the existence, content or results of any arbitration hereunder without the prior written consent of both parties, except
(1) as provided by Section 11 and (2) as may be required by law. The Company shall reimburse Executive for reasonable legal fees incurred in connection with any dispute under this Agreement if Executive prevails
on at least one material issue in such dispute. 

  

	 	(i)	 Effect of Other Law. Anything herein to the contrary notwithstanding, the terms of this Agreement shall
be modified to the extent required to meet the provisions of the Sarbanes-Oxley Act of 2002, Section 409A, the Dodd-Frank Wall Street Reform and Consumer Protection Act or other law applicable to the employment arrangements between Executive
and the Company. Any delay in providing benefits or payments or any failure to provide a benefit or payment shall not in and of itself constitute a breach of this Agreement as a result of applicable law; provided, however, that the
Company shall provide economically equivalent payments or benefits to Executive to the extent permitted by law as soon as practicable after such benefits or payments are due. Any request or requirement that Executive repay compensation that is
required under the first sentence of this Section 16(i), or pursuant to a Company policy that is applicable to other executive officers of the Company and that is designed to advance the legitimate corporate
governance objectives of the Company, shall not in and of itself constitute a breach of this Agreement. 

  

	 	(j)	 Governing Law. This Agreement shall be governed by and construed and enforced in accordance with the
laws of the Commonwealth of Massachusetts applicable to contracts executed in and to be performed entirely within such State, without giving effect to the conflict of law principles thereof. 

  
 22 

	 	(k)	 No Conflicts. As a condition to the effectiveness of this Agreement, Executive represents and warrants
to the Company that Executive is not a party to or otherwise bound by any agreement or arrangement (including, without limitation, any license, covenant, or commitment of any nature), or subject to any judgment, decree, or order of any court or
administrative agency, that would conflict with or will be in conflict with or in any way preclude, limit or inhibit Executive’s ability to execute this Agreement or to carry out Executive’s duties and responsibilities hereunder. In the
event that the Company reasonably determines that Executive’s duties hereunder may conflict with an agreement or arrangement to which Executive is bound, the Company and Executive shall engage in good faith discussions regarding such conflict
and, if such conflict exists, Executive shall be required to cease engaging in any such activities, duties or responsibilities (including providing supervisory services over certain subsets of the Company’s business operations) and the Company
will take steps to restrict Executive’s access to, and participation in, any such activities, until the Company determines that such conflict ceases to exist. Any actions taken by the Company under this
Section 16(k) to restrict or limit Executive’s access to information or provision of services shall not constitute Good Reason for purposes of Section 7(e) hereof.

  

	 	(l)	 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. 

  

	 	(m)	 Effectiveness of Agreement. The effectiveness of this Agreement is contingent upon the occurrence of the
Commencement Date within the time provided in Section 1 hereof. 

 17. Entire Agreement.
This Agreement constitutes the entire agreement between the parties hereto and supersedes all prior agreements, term sheets, understandings and arrangements, oral or written, between the parties hereto with respect to the subject matter hereof,
including without limitation any term sheets or other similar presentations (in each case of the foregoing, other than with respect to any intellectual property related matters addressed in any such prior agreements, term sheets, understandings or
arrangements). 
 18. Counterparts. This Agreement may be executed in separate counterparts, any one of which need not contain
signatures of more than one party, but all of which taken together will constitute one and the same Agreement. Signatures transmitted via facsimile or PDF will be deemed the equivalent of originals. 

[Remainder of page left intentionally blank] 

  
 23 

 IN WITNESS WHEREOF, the parties have executed this Employment Agreement as of the day and
year first above written, to be effective as of the Effective Date. 
  

			
	AMERICAN WELL CORPORATION
		
	By:	 	 /s/ Bradford F. Gay

	Name:	 	Bradford F. Gay
	Title:	 	Senior Vice President and General Counsel
	
	EXECUTIVE
		
	By:	 	 /s/ Roy Schoenberg

	Name:	 	Roy Schoenberg

 Signature Page to Roy Schoenberg Employment AgreementEX-10.22

 Exhibit 10.22 

To: 
 Keith Anderson 

Employment Offer Letter 
 Dear Keith, 

I am pleased to provide you with a summary of the terms and conditions of your anticipated employment by American Well. We hope you choose to
join the American Well team and look forward to a mutually beneficial relationship. 
 1. Position. Your position will be as
Chief Financial Officer, reporting to CEO Dr. Ido Schoenberg, and working from the Company’s Boston, MA office. As an American Well employee, we expect that you will perform all duties and responsibilities normally associated with your
position. Your performance will be reviewed formally on periodic basis and/or after reaching specific milestones for as long as you remain employed by American Well. 

Your responsibilities include, but are not limited to the following: 
  

	 	•	 	 Leading the finance and accounting department, including hiring decisions to prepare for a public offering and to
support the accounting and finance functions of a large, high-growth technology company; 

  

	 	•	 	 Lead M&A efforts, subject to corporate strategy and CEO guidance; and 

 

	 	•	 	 Together with the CEO, lead all IPO efforts. 

2. Starting Date/Nature of Relationship. If you accept this offer, your employment with American Well will officially begin August 9
or such other date as you select during August 2018 (your “Start Date”). Commencing on your Start Date, you will be required to devote all your working time to the performance of your duties at American Well. Your employment with
American Well is at-will, which may be terminated by you or American Well at any time for any reason, subject to the terms of this letter. No provision of this letter shall be construed to create a promise of
employment for any specific period. 
 3. Compensation and Benefits. Commencing on your Start Date, you will receive the following: 

 

	 	A.	 Base Salary: Your base pay shall be at a rate of $400,000.00 per year (the “Base
Salary”), minus customary deductions for federal and state taxes. Your Base Salary will be reviewed by the Compensation Committee (“Committee”) of the Board of Directors (the “Board”), at least annually,
and may be increased in the sole discretion of the Committee, which increased amount shall be the “Base Salary” for purposes of this letter. 

  

	 	B.	 Restricted Stock Units: The Board has approved an award to you (the “RSU Award”) of
Restricted Stock Units (“RSUs”) representing 200,416 shares of the Company’s common stock. The Company represents that the RSU Award equals 1% of the fully-diluted outstanding capital stock of the Company according to the
Company’s current capitalization as of the date of this letter (and has a current value of approximately $9.71 million using our most recent 409A valuation), and you and the Company agree to “true up” or “true down” any
deficiency in the number of shares underlying the RSUs in the case that such representation is determined to be incorrect. 

Current Grant. 25% of the RSU Award (the “Current Grant”), representing 50,104 shares, will be granted to you within
one (1) week of your Start Date and will be fully vested and immediately settled in common stock of the Company as of such date, pursuant to the terms of our form of RSU agreement and the American Well 2006 Employee, Director and Consultant
Stock Plan, as amended (the “2006 Plan”), provided that such terms shall not be inconsistent with this letter in any material respect. 

 Future Grant. The remaining 150,312 shares of stock represented by your RSU Award
(the “Future Grant”) will be granted to you upon the earliest of (i) the effective date of the initial public offering of the Company’s common stock (the “IPO Date”), and (ii) the one-year anniversary of your Start Date. These RSUs will vest and settle in accordance with the following schedule: with respect to 1/9 of the RSUs issued pursuant to the Future Grant, upon the 12-month anniversary of your Start Date, and an additional 1/9 of such RSUs every three (3) months thereafter until such RSUs are vested in full (100% vested after 36 months). These RSUs will be granted
under the Company’s equity compensation plan that it intends to adopt in connection with the IPO or an amended or successor plan to the 2006 Plan, as applicable, and will otherwise be governed by the terms of such plan, provided that such terms
shall not be inconsistent with this letter in any material respect. The Company agrees to take all action to obtain any needed approvals to make the Future Grant. 

Anti-dilution adjustment of number of shares represented by RSUs: In the event that any Series A, B or C Preferred Shares are
converted at a ratio of greater than 1:1 (such as upon an initial public offering of the Company’s common stock, or upon liquidation, merger or change of control of the Company), then immediately prior to such event, the number of shares
of stock to be granted to you pursuant to your RSU Award shall be increased (but not decreased) by any liquidation preference or conversion ratio exercised by the Series A, B or C Preferred Stockholders so that all shares of stock granted pursuant
to your RSU Award shall equal in the aggregate 1% of the outstanding capital stock of the Company on a fully diluted basis as of your Start Date. The adjusted amount of shares issued pursuant to the RSU Award will vest in the same
proportion as the shares represented by RSUs pursuant to this letter as if they had been awarded on the Start Date at the same time as the original RSUs awarded in Section 3(B) of this letter. “Fully diluted basis” means, as of the
time of determination, the sum of (x) the number of issued and outstanding shares of the Company’s capital stock, plus (y) the total number of shares of the Company’s capital stock issuable upon the exercise, exchange or
conversion of all any convertible securities of the Company issued and outstanding at such time, whether or not vested or presently exercisable, plus (z) the total number of shares of the Company’s capital stock reserved by the Board and
available for issuance under the 2006 Plan. 
 Effective as of the IPO Date, and after any applicable adjustment pursuant to the preceding
paragraph, the preceding paragraph shall no longer apply, and any adjustments or anti-dilution measures taken with respect to the Current Grant shall be treated in accordance with the terms of the 2006 Plan, including Section 23 thereunder
relating to adjustments. The Future Grant will be subject to the anti-dilution or adjustment provisions contained in the plan under which the Future Grant is made. For the avoidance of doubt, any adjusted Current Grant and/or Future Grant shall
continue to vest on the same schedule as provided in Section 3(B) of this letter and there shall be no duplication of application of the anti-dilution and/or adjustment provisions contained in this letter and any equity compensation plan(s)
under which the RSU Award is granted. 
 In connection with any anti-dilution event covered by this Section the Company shall ensure that
there are sufficient shares of common stock available for issuance under an incentive plan to fulfill the Company’s obligations hereunder. 

Beginning in 2019, and thereafter, you shall be eligible to participate in any Company long term incentive program for Company officers or
other equity incentive plan, as established in the future. For clarity, nothing in this paragraph shall obligate Company to grant you additional equity in Company as part of any long-term incentive program or other equity incentive plan. 

	 	C.	 Incentive Compensation: You will be eligible to receive an annual discretionary cash bonus with a target
value of 100% of your Base Salary, payable after the close of the applicable fiscal year but in any event prior to March 15 of the following calendar year. Other than as set forth below, the criteria for, and attainment of, your discretionary
bonuses will be at the sole discretion of the Committee and based on the achievement of both corporate and personal performance objectives. 

Your bonus for 2018, if any, will be based the achievement of the following KPIs (subject to the Company’s attainment of its goals): 

 

	 	•	 	 Building a high performing, culturally aligned finance team and financial infrastructure capable of supporting
the reporting demands of a public company. This includes but is not limited to the ability to successfully create a compliance and performance driven public company framework capable of producing the required deliverables, reports, procedures,
management tools, and underlying support systems, including accounting and financial reporting systems, by the end of year 2018 (75%); and 

  

	 	•	 	 Successful IPO during 2018 or closing of material M&A(s) with value of $50MM or more during 2018 (25%).

  

	 	D.	 Travel & Accommodation Expense: 

 

	 	a.	 Until July 1, 2019, the Company shall provide furnished housing for your use in Boston near the
Company’s corporate office, MA metropolitan area. Such accommodations will provide executive living and the cost of such accommodations will be approved by the CEO and borne by the Company as an expense. If such housing is a rented or leased
apartment, the Company will pay for rent and utilities. 

  

	 	b.	 The Company shall reimburse you for the reasonable costs of moving your household goods and cars from your
current residence to the Boston, Massachusetts metropolitan area, and reasonable expenses associated with up to four family house-hunting trips. 

  

	 	c.	 You will be reimbursed for all reasonable travel expenses which you will incur travelling to and from the
Company’s Boston office on a weekly basis until July 1, 2019. All expenses must comply with the Company’s expense reimbursement policy. 

  

	 	E.	 Other Benefits: You will be eligible to participate in the various benefits offered by American Well on
terms and conditions no less favorable than other senior officers of the Company, including American Well’s group medical and dental plans, life and disability insurance, employee contributed 401k, 401k matching contributions from the Company
and paid vacation time. Benefits may be modified or changed from time to time at the sole discretion of American Well, and the provision of such benefits to you in no way changes or impacts your status as an
at-will employee. American Well’s present benefit structure and other important information about the benefits for which you may be eligible are described in the benefits summary booklet and in the
employee handbook that you will receive upon the commencement of your employment. Where a benefit is subject to a formal plan (for example, medical insurance or life insurance), eligibility to participate in and receive any particular benefit is
governed solely by the applicable plan document. 

  

	 	F.	 Personal Time Off: You are entitled to participate in American Well’s unlimited Personal Paid Time
Off Policy. 

 4. Severance. In the event that your employment with American Well is terminated by the Company without
Cause or by you for Good Reason (both as defined below) and provided you execute a separation agreement containing a general release substantially in the form attached hereto as Exhibit A (the “Release”), and allow it to become
effective within 60 days (the date that the Release becomes effective and may no longer be revoked by you, shall be referred to as the “Release Date”), then American Well will provide you with the following severance benefits (the
“Severance Benefits”): 

	 	A.	 You will receive an amount equal to your Base Salary, less applicable withholding and deductions, paid in equal
installments on American Well’s regular payroll dates during the one (1) year period following the Release Date (the “Severance Period”), with the first such payment made on the Payment Date (defined below).

  

	 	B.	 If you are participating in American Well’s group health insurance plans on the effective date of
termination, and you timely elect and remain eligible for continued coverage under the Consolidated Omnibus Budget Reconciliation Act (“COBRA”), or, if applicable, state or local insurance laws, American Well shall pay that portion
of your COBRA premiums that American Well was paying prior to the effective date of termination for the Severance Period or for the continuation period for which you are eligible, whichever is shorter. 

 

	 	C.	 Additionally, on the Payment Date, the Company will pay you, in a lump sum payment, an amount equal to the pro-rata portion of your earned Incentive Compensation annual bonus target for the year in question. Such amount shall be calculated based on the Company’s determination of both (i) its attainment of its
corporate goals, and (ii) your attainment of your personal KPIs, and also on the number of days remaining in the then current fiscal year, each as of the date of your termination. 

 

	 	D.	 Any RSUs or other equity awards, if any, that are outstanding but then-unvested and are scheduled to vest
within one year of the date of termination, and any portion of the RSU Award that was promised in Section 3(B) but not yet granted at the time of termination but which would be scheduled to vest within one year of the date of termination, shall
be vested and immediately settled in stock; provided however that if such termination occurs within two (2) years after a “Sale Event”, then the entire unvested RSU Award shall become fully vested and settled in stock. For this
purpose, a “Sale Event” means the cumulative acquisition of over fifty percent (50%) of the outstanding Common Stock of Company. 

You shall not receive any of the benefits pursuant to this Section 4 unless you execute the Release within the consideration period specified therein.
The Payment Date shall be the first regular payroll date following the Release Date (define above) provided however, that if the period during which you may consider and sign the Release spans two calendar years then the Payment Date shall be the
later of (1) the first payroll date in such second calendar year or (2) the Release Date). Your ability to receive benefits pursuant to Section 4 is further conditioned upon: your returning all Company property; complying with your
post-termination obligations under this Offer Letter and the Restrictive Covenant Agreement (defined below); and complying with the Release. 
 For purposes
of this Section 4, “Cause” means: (i) indictment or conviction of any felony or of any crime involving dishonesty or moral turpitude; (ii) your breach, in any material respect, of this Offer Letter or the Restrictive
Covenant Agreement attached hereto as Exhibit B; (iii) your refusal to abide by or comply with any reasonable, lawful directives of the CEO or the Board; (iv) your willful dishonesty, fraud, or material misconduct with respect to the
business or affairs of American Well; (v) intentional damage to any property of American Well; or (vi) conduct by you which demonstrates gross unfitness to serve. 

For purposes of this letter, the following will constitute “Good Reason”: 

1. the Company materially diminishes your duties, authorities or responsibilities, changes your reporting responsibilities, or removes you from the position of
Chief Financial Officer. For the avoidance of doubt, if the Company is acquired by or merged into another entity, and you are not the Chief Financial Officer reporting to the CEO of the buyer or resulting parent entity, then your duties and
authority will be deemed to have been materially reduced for purposes of this Good Reason definition; 
 2. material adverse reduction in the amount of
aggregate cash compensation which you have the opportunity to earn or failure by the Company to pay such compensation, except where such reduction occurs contemporaneously with the implementation of a firm-wide cost-reduction program affecting
comparable executives; 

 3. The Company relocates your principal place of employment to a metropolitan area other than the Boston
metropolitan area or the Minneapolis metropolitan area; or 
 4. a material breach of this letter by the Company. 

In all respects, the definition of Good Reason shall be interpreted to comply with Code Section 409A, and any successor statute, regulation and guidance
thereto. 
 You shall not be considered to have terminated your employment for Good Reason unless you have (A) reasonably determined in good faith that
a Good Reason condition has occurred; (B) not provided your express written consent to the occurrence that you allege constitutes Good Reason; (C) given the Company written notice of termination for Good Reason not more than sixty
(60) days after the initial existence of the alleged condition giving rise to Good Reason; (D) given the Company at least thirty (30) days after receipt of such notice to cure the alleged deficiency; and (E) terminated your
employment within sixty (60) days following the Company’s receipt of such notice.
 5. Confidentiality The Company considers
the protection of its confidential information, proprietary materials and goodwill to be extremely important. In addition, as is true of all American Well employees, you will be required to sign the Company’s form agreement relating to
confidentiality, non-competition, non-solicitation and work product (the “Restrictive Covenant Agreement”) before your Start Date as a condition of this
offer of employment. Notwithstanding anything to the contrary in the Restrictive Covenant Agreement and subject to your compliance with the confidentiality obligations and commitments therein, the Company hereby agrees that you will not be deemed in
breach of the non-competition clause in the Restrictive Covenant Agreement if during the 1 year following the termination of your employment with the Company you provide investment banking services or work for
a private equity firm involving services or investment to companies that are not providing telehealth products or services. For clarity, you may provide investment banking investment banking services or work for a private equity firm involving
services or investment to companies that have a telehealth offering as long as the services provided are not to the telehealth division or business of such entity. 

6. Whistleblower; DTSA. Nothing in this letter or otherwise limits your ability to communicate directly with and provide information,
including documents, not otherwise protected from disclosure by any applicable law or privilege to the Securities and Exchange Commission (the “SEC”), any other federal, state or local governmental agency or commission
(“Government Agency”) or self-regulatory organization regarding possible legal violations, without disclosure to the Company. The Company may not retaliate against you for any of these activities, and nothing in this letter
requires you to waive any monetary award or other payment that you might become entitled to from the SEC or any other Government Agency or self-regulatory organization. 

Pursuant to the Defend Trade Secrets Act of 2016, the parties hereto acknowledge and agree that you shall not have criminal or civil liability under any
Federal or State trade secret law for the disclosure of a trade secret that (A) is made (i) in confidence to a Federal, State, or local government official, either directly or indirectly, or to an attorney and (ii) 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. In addition and without limiting the preceding
sentence, if you file a lawsuit for retaliation by the Company for reporting a suspected violation of law, you may disclose the trade secret to your attorney and may use the trade secret information in the court proceeding, if you (X) file any
document containing the trade secret under seal and (Y) do not disclose the trade secret, except pursuant to court order. 

 7. Background Check Your employment with the Company is conditioned upon our receipt of
satisfactory results to a background check. Due to the sensitive nature of health data handled by the Company, the Company is obligated by certain client contracts to perform periodic background checks on each of its employees. If you refuse to
authorize the background check or the results of the background check are not satisfactory, the Company reserves the right to withdraw its offer of employment to you or terminate your employment. 

8. Before You Start Your employment with American Well is conditioned on your eligibility to work in the United States. On your first day,
you must complete an I-9 Form and provide American Well with any of the accepted forms of identification specified on the I-9 Form. A copy of an I-9 Form is enclosed for your information. If your status requires a work authorization from the INS (e.g. New H1B visa petition or endorsement from another company), documented proof of work eligibility must be
furnished and confirmed prior to your first day of work. 
 9. Section 409A This letter is intended to comply with, or otherwise be
exempt from, Section 409A of the Code and any regulations and Treasury guidance promulgated thereunder. The Company shall undertake to administer, interpret, and construe this letter, to the extent reasonably practicable, in a manner that does
not result in the imposition on you of any additional tax, penalty, or interest under Section 409A of the Code. If the Company determines in good faith that any provision of this letter would cause you to incur an additional tax, penalty, or
interest under Section 409A of the Code, the Company and you shall use reasonable efforts to reform such provision, if possible, in a mutually agreeable fashion to maintain to the maximum extent practicable the original intent of the applicable
provision without violating the provisions of Section 409A of the Code. If a payment obligation under this letter arises on account of the your separation from service while you are a “specified employee” (as defined under
Section 409A of the Code), then any payment that constitutes “deferred compensation” (as defined under Treasury Regulation Section 1.409A-1(b)(1), after giving effect to the exemptions in
Treasury Regulation Sections 1.409A-1(b)(3) through (b)(12)) that is scheduled to be paid within six (6) months after such separation from service shall accrue without interest and shall be paid within 15
days after the end of the six-month period beginning on the date of such separation from service or, if earlier, within 15 days after the appointment of the personal representative or executor of your estate
following your death. Notwithstanding the foregoing, nothing in this letter or otherwise is intended to, nor does it, guarantee that the payments and benefits under this letter will not be subject to any “additional tax” or other adverse
tax consequences under Section 409A or any similar state or local tax law. 
 10. D&O Insurance; Indemnification. The Company
shall also cover you under directors’ and officers’ liability insurance (both during and after employment) in an amount and to an extent not less than the level of coverage that the Company provides its other senior officers. The
Company agrees to indemnify you pursuant to the terms of the Indemnification Agreement attached hereto as Exhibit C. 
 11. Legal Fees.
The Company will reimburse legal fees reasonably incurred by you in connection with entering into this letter agreement up to a mutually agreed amount and subject to your payment of all applicable taxes on such amount. 

12. Miscellaneous. This letter constitutes our entire offer regarding the terms and conditions of your prospective employment with
American Well. The terms of your employment shall be governed by the law of Massachusetts. By accepting this offer of employment, you agree that any action, demand, claim or counterclaim in connection with any aspect of your employment with American
Well, or any separation of employment (whether voluntary or involuntary) from American Well, shall be resolved by a judge alone, and you waive and forever renounce your right to a trial before a civil jury. 

You may accept this offer of employment and the terms and conditions hereof by signing the enclosed additional copy of this letter. Your signature on the copy
of this letter and your submission of the signed copy to me will evidence your agreement with the terms and conditions set forth herein. This offer will expire on August 9, 2018 unless accepted by you prior to such date. 

 We are excited to offer you the opportunity to join American Well, and we look forward to having you aboard.
We are pleased that you have chosen to join the American Well team, and confident that you will make an important contribution to our unique and exciting enterprise. 
  

					
	Sincerely,	  		  	
			
	 /s/ Ido Schoenberg
	  	    	  	    
	Dr. Ido Schoenberg	  		  	
	CEO & Chairman of the Board	  		  	

 Acknowledgment: 

I, Keith Anderson, have read, understand, and accept employment on the terms and conditions outlined in this letter. I am not relying on any
representations made to me by anyone other than as set forth above. 
  

					
	 /s/ Keith Anderson
	  	 8/8/2018
	  	    
	Signature	  	Date

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