Document:

Exhibit 10.22

 

SEPARATION AGREEMENT, GENERAL RELEASE, AND WAIVER
OF RIGHTS

 

This SEPARATION AGREEMENT,
GENERAL RELEASE, AND WAIVER OF RIGHTS (“Agreement”) is entered into between Tyson Macdonald residing at 4 Springbriar
Lane, Baltimore, Maryland 21208 (“Employee”), and High Street Capital Partners Service Company, LLC, and any
of its parents, subsidiaries, affiliates, divisions or successors, including but not limited to High Street Capital Partners, LLC
and Acreage Holdings, Inc., as well as their present, former and future officers, directors, members, shareholders, employees and
agents, in both their individual and representative capacities (collectively, the “Company”). The Employee and
the Company may be referred to collectively as “Parties.”

 

1.      Termination
of Employment. Employee’s employment with the Company will terminate and end for all purposes on March 9, 2020 (the
“Separation Date”). As of the Separation Date, Employee will no longer receive any salary, monies or benefits
of any kind either from the Company, or from anyone else because of Employee’s employment with the Company before the Separation
Date, except as expressly provided in this Agreement.

 

2.        Final
Paycheck and Special Consideration.

 

A.     
Employee will receive a final direct deposit with the bank account on file with Justworks on February 28, 2020 for pay up to and
including the Separation Date, which Employee agrees is all that will be due and owing to Employee on and as of the Separation
Date, except as expressly provided in this Agreement. Employee understands and agrees that the final paycheck is made in complete
satisfaction of any and all claims for accrued wages, salary, bonus, profit sharing, commissions, overtime premiums, vacation pay,
holiday pay and any other pay and leave of any kind to which Employee is or may be entitled.

 

B.      
In connection with the termination of Employee’s employment and in return for Employee's waiver of rights against the Company
and Employee signing this Agreement and it becoming effective (without being revoked pursuant to this Agreement), together with
other representations and covenants in this Agreement, the Company agrees as follows, which Employee expressly agrees is adequate
and sufficient consideration:

 

		(i)	Special Separation Payment. The Company shall pay Employee a special
separation payment in the gross amount of $300,000 (“Special Separation Payment”), less all applicable deductions,
which shall be payable in twenty-six equal installments on each of the Company’s regular bi-weekly pay days, beginning with
the first pay day after the Effective Date of this Agreement. Employee understands and agrees that this Special Separation Payment
is monetary consideration to which Employee would not otherwise be entitled if Employee did not sign this Agreement and it did
not become effective.

 

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		(ii)	COBRA Premium. Provided that Employee timely elects COBRA, the
                                                                     Company shall pay Employee’s portion of the cost of the COBRA premium in the gross amount of $28,814.76
                                                                     (“COBRA Premium Payment”), less all applicable deductions, which shall be payable in twenty-six equal
                                                                     installments on each of the Company’s regular
by-weekly pay days, beginning with the first pay day after the Effective Date of this Agreement. Employee further understands and
agrees that this COBRA Premium Payment is monetary consideration to which Employee would not otherwise be entitled if Employee
did not sign this Agreement and it did not become effective.

  

		(iii)	Fringe Benefits Income Tax True-Up Payment. The Company agrees to remit
income tax payments on Employee’s behalf to the IRS and the relevant state taxing authorities associated with Employee’s
New York, New York corporate apartment rent, utilities, and his verified expenses related to travel between Maryland and New York,
up to and including the Separation Date. This payment will be made on Employee’s behalf by no later than July 15, 2020, and
Employee shall receive a statement from the Company reflecting such income tax payments remitted on his behalf.

 

		(iv)	Waiver of Non-Compete. The Company agrees to consider, on a case-by-case
basis, waivers of Employee’s non-competition obligations as set forth in his “Lock-Up and Incentive Agreement”
dated June 27, 2019, such waivers to be granted in the Company’s sole discretion.

 

3.                  Employee’s
General Release and Waiver of Rights to Further Recovery. (A) As a condition of the Company’s willingness to
enter into this Agreement, and in consideration for the agreements contained in this Agreement, Employee, with the intention
of binding himself and each of his heirs, beneficiaries, trustees, administrators, executors, and assigns and legal
representatives (collectively, the “Releasors”), hereby releases, waives and forever discharges (whether
on an individual basis or as a member of a class/collective) the Company from, and hereby acknowledges full accord and
satisfaction of, any and all claims, demands, causes of action, and liabilities of any kind whatsoever (upon any legal or
equitable theory, whether contractual, common law or statutory, under federal, state or local law or otherwise), whether
known or unknown, asserted or unasserted, by reason of any act, omission, transaction, agreement, occurrence or any other
matter whatsoever that the Releasors ever had, now have or hereafter may have against the Company from the beginning of the
world up to and including the date that Employee signs this Agreement.

 

Employee understands
and agrees that the right to further recovery based upon claims which Employee is waiving include but are not limited to claims
arising under federal, state or local laws prohibiting employment discrimination and claims growing out of any legal restrictions
on the Company’s right to terminate its employees. Without limiting the generality of this or the foregoing paragraph, the
Releasors hereby expressly release and forever discharge the Company from:

 

		(i)	any and all claims relating to or arising from Employee’s
prior employment with the Company, the terms and conditions of his employment with the Company, and the cessation of his employment
with the Company;

 

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		(ii)	any and all claims under any federal, state or local
statute or ordinance, public policy or the common law, including, without limitation, any and all claims under the Fair Labor
Standards Act, New York State Labor Law, the New York Compilation of Codes, Rules and Regulations, Title VII of the Civil Rights
Act of 1964, the Civil Rights Acts of 1866, 1871 and 1991, the Age Discrimination in Employment Act, the Older Workers Benefit
Protection Act, the Sarbanes-Oxley Act, the Family & Medical Leave Act, the Consolidated Omnibus Budget Reconciliation Act,
the Americans with Disabilities Act, 42 U.S.C. § 1981, the New York State and New York City Human Rights Laws, the New York
City Living Wage Law, the New York Corrections Law, the federal False Claims Act, the New York False Claims Act; and any similar
state and local law, and the New York and federal Constitutions, and as such laws have been or may be amended;

 

		(iii)	any and all claims for employee benefits, including,
without limitation, any and all claims under the Employee Retirement Income Security Act of 1974, as amended;

 

		(iv)	any and all claims for slander, libel, defamation, negligent
or intentional infliction of emotional distress, personal injury, prima facie tort, loss of consortium, invasion of privacy, negligence,
breach of contract, compensatory or punitive damages, or any other claim for damages or injury of any kind whatsoever; and

 

		(v)	any and all claims for monetary recovery, including,
without limitation, attorneys’ fees, experts’ fees, medical fees or expenses, costs and disbursements and the like.

 

(B)            Agreement Not
To Sue Or Bring Certain Claims. Employee acknowledges and agrees that he is also giving up any right to sue or bring any
claims released in Paragraph 3(A) against or involving the Company, or to become or remain a member of any collective group or
class of persons seeking to bring any such claim(s) against the Company. This Agreement may be used by the Company as a full and
complete defense to any such claim(s), or to dismiss or enjoin any such proceeding involving any such claim(s) instituted or maintained
by Employee.

 

(C)
          Claims That May Be Brought Notwithstanding Agreement. No
provision of this Agreement should be read to prevent Employee from: (1) enforcing the terms of this Agreement; and (2)
filing claims arising for the first time after he executes this Agreement. In addition, nothing in this Agreement shall limit
Employee’s right, where applicable, to file or participate in any non-legally waivable claim or investigative
proceeding with any federal, state, or local governmental agency, including filing a charge with the United States Equal
Employment Opportunity Commission, New York State Division of Human Rights, New York City Commission on Human Rights,
National Labor Relations Board, or Securities and Exchange Commission. However, to the extent permitted by law, Employee
agrees that if such an administrative claim is made, Employee shall not be entitled to recover, accept, or retain any
individual monetary relief or other individual remedies with respect to any matter covered by this Agreement.

 

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4.        Company’s
General Release of Claims. The Company releases and forever discharges Employee and his agents and legal representatives,
from all claims, liabilities, obligations, and/or causes of action of every kind, nature, and character, known or unknown,
suspected and unsuspected, disclosed and undisclosed that the Company may now have, or has ever had, against Employee, up to
and including the execution date of this Amendment. This Release does not include and will not preclude any claims or causes
of action related to claims, actions, or rights arising under or to enforce the terms of this Agreement.

 

5.       Non-Disclosure/Confidentiality.

 

A.     This Agreement.
Employee shall not disclose the negotiations, subject matter, or terms of this Agreement (collectively, “Confidential
Information”). Notwithstanding the previous sentence, Employee may disclose Confidential Information: (i) To Employee’s
own legal, financial, tax advisor(s) and treating medical professionals; (ii) To Employee’s own immediate family, provided
that Employee’s immediate family agree to be bound by this confidentiality provision and that Employee shall be responsible
for any failure to abide by this confidentiality provision; (iii) To taxing authorities or in response to a lawfully-issued subpoena,
notice, or court order, provided that Employee provide written notice to the Company within two business days of receiving any
such subpoena, notice, or order; or (iv) As necessary to enforce the terms of this Agreement.

 

B.       Non-Disclosure
Agreement. Employee acknowledges and agrees that he is a party to a certain “Non-Disclosure Agreement” that he
signed and entered into as of January 3, 2017 (“NDA”). Employee expressly acknowledges and agrees that, notwithstanding
anything to the contrary in this Agreement, all terms and conditions in the NDA shall remain in full force and effect, and that
Employee shall continue to abide by all such terms and conditions.

 

6.        Return of Documents and Property/Exit Interview. Employee represents and warrants that, as of the Separation Date,
he has returned all items, materials and documents created or used by Employee during and in the course of his employment with
Company. The Parties acknowledge that such items, materials and documents to be returned include, but are not necessarily limited
to, all electronic devices, thumb drives, cell phones, computers, passwords, account logons, and contact information; all pending
documents, binders, and files; keys; and other Company documents.

 

7.        Non-Disparagement.
Employee shall not directly or indirectly make any disparaging remarks, whether oral, written or on social media, and whether
such remarks cause actual harm or not, about the Company. It is understood, however, that this Paragraph 6 shall not limit or
restrict Employee from responding in good faith in response to a lawfully-issued subpoena, notice, or court order, provided
that Employee provide written notice to the Company within two business days of receiving any such subpoena, notice, or
order.

 

8.       Employee
Representations and Covenants. As further and specific consideration for the Company’s covenants in this
Agreement, Employee expressly represents and covenants:

 

		(i)	That the Company does not owe Employee any wages or other
compensation, payments, or monies of any kind or nature, other than as expressly provided in this Agreement, that Employee has
been fully and accurately compensated for all hours worked and services provided during his employment with the Company, and that
he does not claim that the Company violated or denied any wage and hour rights under the federal Fair Labor Standards Act, or
any similar state or local law.

 

		(ii)	That Employee has not initiated, filed, submitted, or made any claim, complaint, or charge
                                                                                   with any court, agency, board, department, or other body or office with respect to his prior employment with the Company, the
                                                                                   cessation of his employment with the Company, or any policies, practices or alleged acts or omissions involving the Company. 

 

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		(iii)	That under the federal Family and Medical Leave Act,
as amended, or any similar state or local law (collectively “FMLA”), Employee has received all leave required
or requested, and currently does not, and in the past did not, have any claim for denial of such leave, and does not claim that
the Company violated or denied rights under the FMLA or retaliated against him in any way for exercising any rights under the
FMLA.

 

		(iv)	That, with the exception of any pending claims for Workers’
Compensation benefits that have been submitted in writing to the Company prior to the Separation Date, Employee has not suffered
any job-related injury for which he might be entitled to compensation or relief, such as an injury for which he might receive
a Workers’ Compensation award in the future.

 

9.      
Reference. Upon written request by Employee or a third-party for an employment reference, the Company shall provide
only the following information to the requesting person: (i) Employee’s dates of employment; and (ii) Employee’s title/position
with the Company as of the Separation Date. Employee expressly acknowledges and agrees that the release and waiver set forth in
Paragraph 3 of this Agreement includes any and all claims made or that could be made relating to or arising out of any statements
made or not made by the Company in accordance with this Paragraph 8.

 

10.     
Prior Agreements. Employee agrees and acknowledges that Employee previously entered into certain agreements that
are addressed as follows:

 

		(i)	Restricted Stock Unit Award Agreement (7/10/19).
Employee entered into a certain Restricted Stock Unit Award Agreement signed on or about July 10, 2019, and pursuant to the certain
Lock-Up and Incentive Agreement dated June 27, 2019 (“Prior Agreement No. 1”), which granted 981,836 Restricted
Stock Units (“RSUs”) pursuant to a certain vesting schedule. None of the RSUs have vested as of the Separation
Date, and Employee acknowledges and agrees that any and all other claims, rights and privileges under Prior Agreement No. 1 are
hereby waived, forfeited, and extinguished as of the Separation Date, and Employee shall have no further claims, rights and/or
privileges under Prior Agreement No. 1.

 

		(ii)	Restricted Stock Unit Award Agreement (8/28/19).
Employee entered into a certain Restricted Stock Unit Award Agreement signed on or about August 28, 2019, and pursuant to the
certain Omnibus Incentive Plan dated November 14, 2018 (“Prior Agreement No. 2”), which granted 41,518 RSUs
pursuant to a certain vesting schedule. Employee acknowledges and agrees that, of those, 18,133 RSUs have vested as of the Separation
Date, subject to all other terms and conditions in the Prior Agreement No. 2, and that any and all other claims, rights and privileges
with respect to RSUs that are not vested as of the Separation Date are hereby waived, forfeited, and extinguished as of the Separation
Date, and Employee shall have no further claims, rights and/or privileges to such other unvested RSUs under Prior Agreement No.
2.

 

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		(iii)	Restricted Stock Unit Award Agreement (Undated). Employee entered into a certain undated
Restricted Stock Unit Award Agreement, and pursuant to the certain Omnibus Incentive Plan dated November 14, 2018 (“Prior
Agreement No. 3”), which granted 97,500 RSUs pursuant to a certain vesting schedule. Employee acknowledges and agrees
that, of those, 85,312 RSUs have vested as of the Separation Date, subject to all other terms and conditions in the Prior Agreement
No. 3, and that any and all other claims, rights and privileges with respect to RSUs that are not vested as of the Separation Date
are hereby waived, forfeited, and extinguished as of the Separation Date, and Employee shall have no further claims, rights and/or
privileges to such other unvested RSUs under Prior Agreement No. 3.

 

		(iv)	Restricted Stock Unit Award Agreement (3/13/19).
Employee entered into a certain Restricted Stock Unit Award Agreement signed on or about November 13, 2019, and pursuant to the
certain Omnibus Incentive Plan dated November 14, 2018 (“Prior Agreement No. 4”), which granted 52,500 RSUs
pursuant to a certain vesting schedule. Employee acknowledges and agrees that, of those, 45,937 RSUs have vested as of the Separation
Date, subject to all other terms and conditions in the Prior Agreement No. 4, and that any and all other claims, rights and privileges
with respect to RSUs that are not vested as of the Separation Date are hereby waived, forfeited, and extinguished as of the Separation
Date, and Employee shall have no further claims, rights and/or privileges to such other unvested RSUs under Prior Agreement No.
4.

  

		(v)	Option Award Agreement (11/14/18). Employee entered
into a certain Option Award Agreement signed on or about November 14, 2018, and pursuant to the certain Omnibus Incentive Plan
dated November 14, 2018 (“Prior Agreement No. 5”), which granted 125,000 options pursuant to a certain vesting
schedule. Employee acknowledges and agrees that, of those, 52,083 options have vested as of the Separation Date, subject to all
other terms and conditions in the Prior Agreement No. 5, and that any and all other claims, rights and privileges with respect
to options that are not vested as of the Separation Date are hereby waived, forfeited, and extinguished as of the Separation Date,
and Employee shall have no further claims, rights and/or privileges to such other unvested options under Prior Agreement No. 5.

 

11.      Limited Restricted Covenant. During the Restricted Period, Employee shall not: (i) work at, work for, be employed by, provide services to, engage with, or assist in any way, whether or not for remuneration, recognition, or reward, any person, corporation, organization, or business entity (whether any of those are for profit) that cultivates, produces, sells, or intends to cultivate, produce, or sell, cannabis or cannabis-derived products anywhere in any jurisdiction in which the Company has operations; and (ii) on behalf of himself or another, either directly or indirectly, solicit, hire, or work with any person who is an employee of the Company as of the Separation Date, or who was an employee of the Company within six months after the Separation Date. For purposes of this Agreement, the term “Restricted Period” shall mean the period during which Employee is receiving the Special Separation Payment and the COBRA Premium Payment under this Agreement.

  

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12.      Section 409A.
The intent of the parties is that the payments and benefits under this Agreement comply with or be exempt from Section 409A of
the Internal Revenue Code of 1986, as amended, and the regulations and IRS notices thereunder (“Section 409A”) and,
accordingly, to the maximum extent permitted, this Agreement shall be interpreted to be in compliance therewith. If any provision
of this Agreement would cause Employee to incur any additional tax or interest under Section 409A, the Employee shall be liable
for any additional tax, penalty or interest under Section 409A and the Company shall have no liability for any such tax, penalty
or interest.

 

		(i)	If any payment, compensation or other benefit provided
to Employee under this Agreement in connection with Employee’s “separation from service” (within the meaning
of Section 409A) is determined, in whole or in part, to constitute “nonqualified deferred compensation” within the
meaning of Section 409A and Employee is a specified Employee as defined in Section 409A(2)(B)(i), no part of such payments shall
be paid before the day that is six months plus one day after the date of termination or, if earlier, ten (10) business days following
Employee’s death (the “New Payment Date”). The aggregate of any payments and benefits that otherwise
would have been paid and/or provided to Employee during the period between the date of termination and the New Payment Date shall
be paid to Employee in a lump sum on such New Payment Date. Thereafter, any payments and/or benefits that remain outstanding as
of the day immediately following the New Payment Date shall be paid without delay over the time period originally scheduled, in
accordance with the terms of this Agreement. Notwithstanding anything to the contrary herein, to the extent that the foregoing
delay applies to the provision of any ongoing welfare benefits, Employee shall pay the full cost of premiums for such welfare
benefits due and payable prior to the New Payment Date and the Company shall pay Employee an amount equal to the amount of such
premiums which otherwise would have been paid by the Company during such period within ten (10) business days following its conclusion.

 

		(ii)	A termination of employment shall not be deemed to have occurred for purposes of any provision
of this Agreement providing for the payment of any amounts or benefits subject to Section 409A upon or following a termination
of employment unless such termination is also a “separation from service” within the meaning of Section 409A, and for
purposes of any such provision of this Agreement, references to a “termination,” “terminate,” “termination
of employment” or like terms shall mean separation from service.

 

		(iii)	All expenses or other reimbursements as provided herein shall be payable in accordance with the
Company’s policies in effect from time to time, but in any event shall be made on or prior to the last day of the taxable
year following the taxable year in which such expenses were incurred by Employee.. With regard to any provision herein that provides
for reimbursement of costs and expenses or in-kind benefits, except
as permitted by Section 409A: (i) the right to reimbursement or in-kind benefits shall not be subject to liquidation or exchange
for another benefit; and (ii) the amount of expenses eligible for reimbursements or in-kind benefits provided during any taxable
year shall not affect the expenses eligible for reimbursement or in-kind benefits to be provided in any other taxable year.

  

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

 

		(v)	Notwithstanding any provision of this Agreement to the
contrary, if any provision in the Agreement contravenes any regulations or guidance promulgated under Section 409A, or would cause
any either the Company or the Employee to be subject to additional taxes, interest and/or penalties under Section 409A, such provision
of this Agreement may be modified by the Company without notice and consent of Employee in any manner that the Company deems reasonable
or necessary to avoid adverse consequences under Section 409A. In making such modifications the Company shall attempt, but shall
not be obligated, to maintain, to the maximum extent practicable, the original intent of the applicable provision without contravening
the provisions of Section 409A.

 

13.     
Entire Agreement. This Agreement sets forth the entire agreement between Employee and the Company, and supersedes
any prior written, oral or implied agreements or representations between them as to the subject matter of this Agreement (except
where expressly noted in this Agreement). This Agreement may only be amended by a written agreement signed by Employee and an authorized
representative of the Company.

 

14.     
Governing Law/Enforcement. This Agreement has been negotiated, executed, and entered into in the County of New York,
State of New York, and shall be governed by and construed in accordance with the internal laws of the State of New York, without
giving effect to principles of conflict of laws. In the event of a dispute arising out of or relating to this Agreement, any action
or proceeding shall be brought exclusively in a state or federal court of competent jurisdiction in the County of New York, State
of New York, and the Parties waive any and all objections or defenses based on personal jurisdiction, venue, and forum non conveniens.
In the event the either party is successful in interpreting or enforcing any of the provisions of this Agreement, the prevailing
party shall be entitled to its reasonable attorneys’ fees and costs in any such action or proceeding.

 

15.      Non-Admission.
The Parties recognize and acknowledge that the Company does not admit any liability, wrongdoing, or that it took any unlawful
action with regard to Employee’s employment with or separation from the Company because it is entering into this
Agreement.

 

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16.      Savings Clause.
In the event any provision of this Agreement is held to be invalid, illegal or unenforceable in any respect or for any reason,
the same shall not affect any other provision of this Agreement, and this Agreement shall be construed as if such invalid, illegal
or unenforceable provision had never been contained herein. All provisions of this Agreement shall be enforced to the greatest
extent possible and lawful.

 

17.      Notice.
Except as may otherwise be set forth in this Agreement, any notice, request, authorization or other communication to be made under
this Agreement shall be in writing and shall be deemed to have been duly given if mailed by overnight mail, or by registered or
certified mail, return receipt requested, addressed to the respective address of each party set forth below, or to such other address
as each of the Parties may designate by proper notice.

 

If to Employee:

 

Mr. Tyson Macdonald

4 Springbriar Lane_____ 

Baltimore, Maryland 21208

 

If to the Company:

 

James A. Doherty, III, Esq.

366 Madison Ave.,
11th Floor 

New York, NY 10017____

 

18.     Free
and Voluntary Act. In accordance with the federal Age Discrimination in Employment Act (“ADEA”) and the Older
Workers Benefit Protection Act, Employee expressly acknowledges and agrees:

 

		(a)	This letter is written in terms that Employee fully understands.

 

		(b)	Through this Agreement, Employee is specifically releasing rights and claims
under the ADEA.

 

		(c)	Employee is not waiving any rights or claims that may arise after Employee
signs this Agreement.

 

		(d)	Employee’s release and waiver of claims in this Agreement is in exchange
for consideration to which Employee would not otherwise be entitled to receive, and that Employee would not have received, unless
Employee signed this letter and it became effective.

 

		(e)	Employee has been advised to consult with an attorney
of Employee’s own choosing prior to entering into this Agreement, and Employee has had an opportunity to do so if Employee
so chose.

 

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	 	(f)	Employee had at least 21 consecutive days from receipt of this letter to decide whether or not to enter into this Agreement. Employee
further acknowledges that Employee may sign this Agreement at any time prior to the expiration of the 21-consecutive-day period, and acknowledges
that, if Employee does so, Employee does so completely voluntarily.

 

	 	(g)	Employee has 7 consecutive days
after Employee signs this Agreement to revoke this Agreement. To revoke Agreement after it is signed, Employee must submit a written
letter of revocation, signed by Employee, either by personal delivery for which Employee receives a written receipt, or by overnight
or certified mail (return receipt requested) to the Company at the address set forth in Paragraph 15 of this Agreement. To be effective,
such signed, written letter of revocation must be received by the Company on or before 5:00 p.m. ET on the 7th consecutive
day after Employee signs this Agreement. This Agreement shall become effective on the 8th consecutive day after Employee
signs this Agreement and provides an original, signed Agreement to the Company, provided that Employee did not earlier revoke this
Agreement in accordance with this Paragraph 16 ("Effective Date").

 

IN WITNESS WHEREOF,
the parties hereto knowingly and voluntarily executed this Agreement as of the date set forth below:

 

	TYSON MACDONALD	 	HIGH STREET CAPITAL PARTNERS SERVICE COMPANY, LLC
	 	 	 	 
		 	By:	
	 	 	 	 
	Dated: April 13, 2020	 	Name:	Robert J. Daino
	 	 	Title:	Chief Operating Officer
		 	Dated: 	April 13, 2020

  

    10Exhibit 10.5

 

CAPITOL INVESTMENT CORP. VII

1300 17th Street North, Suite 820

Arlington, Virginia 22209

 

January 22, 2021

 

Capitol Acquisition Management VII LLC

1300 17th Street North, Suite 820

Arlington, Virginia 22209

 

Re: Securities Subscription Agreement

 

Ladies and Gentlemen:

 

This agreement (this
“Agreement”) is entered into on January 22, 2021 by and between Capitol Acquisition Management VII LLC,
a Delaware limited liability company (the “Subscriber” or “you”), and Capitol
Investment Corp. VII, a Delaware corporation (the “Company”, “we” or “us”).
Pursuant to the terms hereof, the Company hereby accepts the offer the Subscriber has made to purchase 7,284,100 shares (the “Shares”)
of the Company’s Class B common stock, $0.0001 par value per share (the “Class B Common Stock”),
up to 950,100 of which are subject to forfeiture by you if the underwriters of the initial public offering (the “IPO”)
of units (the “Units”) of the Company, do not fully exercise their over-allotment option (the “Over-allotment
Option”). The Company’s and the Subscriber’s agreements regarding such Shares are as follows:

 

Article
I.

Purchase of Securities

 

Section 1.01 Purchase
of Shares. For the sum of $15,835 (the “Purchase Price”), which the Company acknowledges receiving in the
form of a capital contribution, the Company hereby issues the Shares to the Subscriber, and the Subscriber hereby purchases the
Shares from the Company, subject to forfeiture, on the terms and subject to the conditions set forth in this Agreement. Concurrently
with the Subscriber’s execution of this Agreement, the Company shall, at its option, deliver to the Subscriber a certificate
registered in the Subscriber’s name representing the Shares (the “Original Certificates”), or
effect such delivery in book-entry form.

 

Article
II.

Representations, Warranties and Agreements

 

Section 2.01 Subscriber’s
Representations, Warranties and Agreements. To induce the Company to issue the Shares to the Subscriber, the Subscriber hereby
represents and warrants to the Company and agrees with the Company as follows:

 

(a) No
Government Recommendation or Approval. The Subscriber understands that no federal or state agency has passed upon or made any
recommendation or endorsement of the offering of the Shares.

 

     

     

    

 

(b) No
Conflicts. The execution, delivery and performance of this Agreement and the consummation by the Subscriber of the transactions
contemplated hereby do not violate, conflict with or constitute a default under (i) the formation and governing documents of the
Subscriber, (ii) any agreement, indenture or instrument to which the Subscriber is a party, (iii) any law, statute, rule or
regulation to which the Subscriber is subject or (iv) any agreement, order, judgment or decree to which the Subscriber is subject.

 

(c) Organization
and Authority. The Subscriber is a Delaware limited liability company, validly existing and in good standing under the laws
of Delaware and possesses all requisite power and authority necessary to carry out the transactions contemplated by this Agreement.
Upon execution and delivery by you, this Agreement is a legal, valid and binding agreement of the Subscriber, enforceable against
the Subscriber in accordance with its terms, except as such enforceability may be limited by applicable bankruptcy, insolvency,
fraudulent conveyance or similar laws affecting the enforcement of creditors’ rights generally and subject to general principles
of equity (regardless of whether enforcement is sought in a proceeding at law or in equity).

 

(d) Experience,
Financial Capability and Suitability. The Subscriber is: (i) sophisticated in financial matters and is able to evaluate the
risks and benefits of the investment in the Shares and (ii) able to bear the economic risk of its investment in the Shares
for an indefinite period of time because the Shares have not been registered under the U.S. Securities Act of 1933, as amended
(the “Securities Act”), and therefore cannot be sold unless subsequently registered under the Securities Act
or an exemption from such registration is available. The Subscriber is capable of evaluating the merits and risks of its investment
in the Company and has the capacity to protect its own interests. The Subscriber must bear the economic risk of this investment
until the Shares are sold pursuant to: (i) an effective registration statement under the Securities Act or (ii) an exemption from
registration available with respect to such sale. The Subscriber is able to bear the economic risks of an investment in the Shares
and to afford a complete loss of the Subscriber’s investment in the Shares.

 

(e) Access
to Information; Independent Investigation. Prior to the execution of this Agreement, the Subscriber has had the opportunity
to ask questions of and receive answers from representatives of the Company concerning an investment in the Company, as well as
the finances, operations, business and prospects of the Company, and the opportunity to obtain additional information to verify
the accuracy of all information so obtained. In determining whether to make this investment, the Subscriber has relied solely on
the Subscriber’s own knowledge and understanding of the Company and its business based upon the Subscriber’s own due
diligence investigation and the information furnished pursuant to this paragraph. The Subscriber understands that no person has
been authorized to give any information or to make any representations which were not furnished pursuant to this Article II
and the Subscriber has not relied on any other representations or information in making its investment decision, whether written
or oral, relating to the Company, its operations and/or its prospects.

 

    2

     

    

 

(f) Regulation
D Offering. The Subscriber represents that it is an “accredited investor” as such term is defined in Rule 501(a)
of Regulation D under the Securities Act, and acknowledges the sale contemplated hereby is being made in reliance on a private
placement exemption to “accredited investors” within the meaning of Section 501(a) of Regulation D under
the Securities Act or similar exemptions under state law.

 

(g) Investment
Purposes. The Subscriber is purchasing the Shares solely for investment purposes, for the Subscriber’s own account and
not for the account or benefit of any other person, and not with a view towards the distribution or dissemination thereof. The
Subscriber did not decide to enter into this Agreement as a result of any general solicitation or general advertising within the
meaning of Rule 502 of Regulation D under the Securities Act.

 

(h) Restrictions
on Transfer; Shell Company. The Subscriber understands the Shares are being offered in a transaction not involving a public
offering within the meaning of the Securities Act. The Subscriber understands the Shares will be “restricted securities”
within the meaning of Rule 144(a)(3) under the Securities Act, and the Subscriber understands that the certificates or book
entries representing the Shares will contain a legend in respect of such restrictions. If, in the future, the Subscriber decides
to offer, resell, pledge or otherwise transfer the Shares, such Shares may be offered, resold, pledged or otherwise transferred
only pursuant to (i) registration under the Securities Act or (ii) an available exemption from registration. The Subscriber agrees
that if any transfer of its Shares or any interest therein is proposed to be made, as a condition precedent to any such transfer,
the Subscriber may be required to deliver to the Company an opinion of counsel satisfactory to the Company. Absent registration
or an exemption, the Subscriber agrees not to resell the Shares. The Subscriber further acknowledges that because the Company is
a shell company, Rule 144 may not be available to the Subscriber for the resale of the Shares until one year following consummation
of the initial business combination of the Company, despite technical compliance with the requirements of Rule 144 and the release
or waiver of any contractual transfer restrictions.

 

(i) No
Governmental Consents. No governmental, administrative or other third party consents or approvals are required, necessary or
appropriate on the part of Subscriber in connection with the transactions contemplated by this Agreement.

 

Section 2.02 Company’s
Representations, Warranties and Agreements. To induce the Subscriber to purchase the Shares, the Company hereby represents
and warrants to the Subscriber and agrees with the Subscriber as follows:

 

(a) Organization
and Corporate Power. The Company is a corporation duly organized, validly existing and in good standing under the laws of the
State of Delaware. The Company possesses all requisite corporate power and authority necessary to carry out the transactions contemplated
by this Agreement.

 

    3

     

    

 

(b) No
Conflicts. The execution, delivery and performance of this Agreement and the consummation by the Company of the transactions
contemplated hereby do not violate, conflict with or constitute a default under (i) the Certificate of Incorporation or Bylaws
of the Company, (ii) any agreement, indenture or instrument to which the Company is a party, (iii) any law, statute, rule
or regulation to which the Company is subject or (iv) any agreement, order, judgment or decree to which the Company is subject,
except, with respect to clauses (ii), (iii) and (iv) above, where such violation, conflict or default would not reasonably be expected
to have a material adverse effect on the financial condition, operating results or assets of the Company.

 

(c) Title
to Securities. Upon issuance in accordance with, and payment pursuant to, the terms hereof, the Shares will be duly and validly
issued, fully paid and nonassessable. Upon issuance in accordance with, and payment pursuant to, the terms hereof, the Subscriber
will have or receive good title to the Shares, free and clear of all liens, claims and encumbrances of any kind, other than (i)
transfer restrictions hereunder and other agreements to which the Shares may be subject which have been notified to the Subscriber
in writing, (ii) transfer restrictions under federal and state securities laws and (iii) liens, claims or encumbrances imposed
due to the actions of the Subscriber.

 

(d) No
Adverse Actions. There are no actions, suits, investigations or proceedings pending, threatened against or affecting the Company
which (i) seek to restrain, enjoin, prevent the consummation of or otherwise affect the transactions contemplated by this Agreement
or (ii) question the validity or legality of any transactions or seek to recover damages or to obtain other relief in connection
with any transactions.

 

Article
III.

Forfeiture of Shares

 

Section 3.01 Partial
or No Exercise of the Over-allotment Option. In the event the Over-allotment Option granted to the underwriters of the IPO
is not exercised in full, the Subscriber acknowledges and agrees that it (or, if applicable, it and any transferees of Shares)
shall forfeit any and all rights to such number of Shares (up to an aggregate of 1,500,000 Shares and pro rata based upon
the percentage of the Over-allotment Option exercised) such that immediately following such forfeiture, the Subscriber (and all
other initial stockholders prior to the IPO, if any) will own an aggregate number of Shares, not including any shares of the Company’s
Class A common stock, par value $0.0001 per share (the “Class A Common Stock” and, together with the
Class B Common Stock, the “Common Stock”), issuable upon exercise of any warrants or any shares of Class
A Common Stock purchased by the Subscriber in the IPO or in the aftermarket, equal to 20% of the issued and outstanding shares
of Common Stock immediately following the IPO.

 

Section 3.02 Termination
of Rights as Stockholder. If any of the Shares are forfeited in accordance with this Article III, then after such
time the Subscriber (or successor in interest), shall no longer have any rights as a holder of such forfeited Shares, and the
Company shall take such action as is appropriate to cancel such forfeited Shares.

 

Section 3.03 Share
Certificates. In the event an adjustment to the Original Certificates, if any, is required
pursuant to this Article III, then the Subscriber shall return such Original Certificates to the Company or its designated
agent as soon as practicable upon its receipt of notice from the Company advising the Subscriber
of such adjustment, following which a new certificate (the “New Certificate”), if any, shall be issued in such
amount representing the adjusted number of Shares held by the Subscriber. The New Certificate, if any, shall be returned to the
Subscriber as soon as practicable. Any such adjustment for any uncertificated securities held by the Subscriber shall be made
in book-entry form.

 

    4

     

    

 

Article
IV.

Waiver of Liquidation Distributions; Redemption Rights

 

In connection with
the Shares purchased pursuant to this Agreement, the Subscriber hereby waives any and all right, title, interest or claim of any
kind in or to any distributions by the Company from the trust account which will be established for the benefit of the Company’s
public stockholders and into which substantially all of the proceeds of the IPO will be deposited (the “Trust Account”),
in the event of a liquidation of the Company upon the Company’s failure to timely complete an initial business combination.
For purposes of clarity, in the event the Subscriber purchases any shares of Class A Common Stock in the IPO or in the aftermarket,
any such shares so purchased shall be eligible to receive any liquidating distributions by the Company. However, in no event will
the Subscriber have the right to redeem any Shares into funds held in the Trust Account upon the successful completion of an initial
business combination.

 

Article
V.

Restrictions on Transfer

 

Section 5.01 Securities
Law Restrictions. In addition to any restrictions to be contained in that certain letter agreement (commonly known as an “Insider
Letter”) to be dated as of the closing of the IPO by and between the Subscriber and the Company, the Subscriber agrees
not to sell, transfer, pledge, hypothecate or otherwise dispose of all or any part of the Common Stock unless, prior thereto (a) a
registration statement on the appropriate form under the Securities Act and applicable state securities laws with respect to the
Common Stock proposed to be transferred shall then be effective or (b) the Company has received an opinion from counsel reasonably
satisfactory to the Company that such registration is not required because such transaction is exempt from registration under
the Securities Act and the rules promulgated by the Securities and Exchange Commission thereunder and all applicable state securities
laws.

 

Section 5.02 Lock-up.
The Subscriber acknowledges that the Securities will be subject to lock-up provisions contained in the Insider Letter.

 

Section 5.03 Restrictive
Legends. Any certificates representing the Common Stock shall have endorsed thereon legends substantially as follows:

 

“THE SECURITIES REPRESENTED
HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY STATE SECURITIES LAWS AND NEITHER THE SECURITIES
NOR ANY INTEREST THEREIN MAY BE OFFERED, SOLD, TRANSFERRED, PLEDGED OR OTHERWISE DISPOSED OF EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION
STATEMENT UNDER SUCH ACT OR SUCH LAWS OR AN EXEMPTION FROM REGISTRATION UNDER SUCH ACT AND SUCH LAWS WHICH, IN THE OPINION OF COUNSEL,
IS AVAILABLE.”

 

“THE SECURITIES REPRESENTED
BY THIS CERTIFICATE ARE SUBJECT TO A LOCK-UP AND MAY NOT BE OFFERED, SOLD, TRANSFERRED, PLEDGED OR OTHERWISE DISPOSED DURING THE
TERM OF THE LOCK-UP.”

 

    5

     

    

 

Section 5.04 Additional
Shares or Substituted Securities. In the event of the declaration of a stock dividend, the declaration of an extraordinary
dividend payable in a form other than Common Stock, a spin-off, a stock split, an adjustment in conversion ratio, a recapitalization
or a similar transaction affecting the Company’s outstanding Common Stock without receipt of consideration, any new, substituted
or additional securities or other property which are by reason of such transaction distributed with respect to any Common Stock
subject to this Article V or into which such Common Stock thereby becomes convertible shall immediately be subject
to this Article V and Article III. Appropriate adjustments to reflect the distribution of such securities
or property shall be made to the number and/or class of Common Stock subject to this Article V and Article III.

 

Section 5.05 Registration
Rights. The Subscriber acknowledges that the Shares are being purchased pursuant to an exemption from the registration requirements
of the Securities Act and will become freely tradable only after certain conditions are met or they are registered pursuant to
a registration rights agreement to be entered into with the Company prior to the closing of the IPO (the “Registration
Rights Agreement”).

 

Article
VI.

Other Agreements

 

Section 6.01 Further
Assurances. The Subscriber agrees to execute such further instruments and to take such further action as may reasonably be
necessary to carry out the intent of this Agreement.

 

Section 6.02 Notices.
All notices, statements or other documents that are required or contemplated by this Agreement shall be: (i) in writing and delivered
personally or sent by first class registered or certified mail, overnight courier service or facsimile or electronic transmission
to the address designated in writing, (ii) by facsimile to the number most recently provided to such party or such other address
or fax number as may be designated in writing by such party and (iii) by electronic mail, to the electronic mail address
most recently provided to such party or such other electronic mail address as may be designated in writing by such party. Any
notice or other communication so transmitted shall be deemed to have been given on the day of delivery, if delivered personally,
on the business day following receipt of written confirmation, if sent by facsimile or electronic transmission, one business day
after delivery to an overnight courier service or five days after mailing if sent by mail.

 

Section 6.03 Entire
Agreement. This Agreement, together with the Insider Letter and the Registration Rights Agreement, each substantially in the
form to be filed as an exhibit to the Registration Statement on Form S-1 associated with the IPO, embodies the entire agreement
and understanding between the Subscriber and the Company with respect to the subject matter hereof and supersedes all prior oral
or written agreements and understandings relating to the subject matter hereof. No statement, representation, warranty, covenant
or agreement of any kind not expressly set forth in this Agreement shall affect, or be used to interpret, change or restrict,
the express terms and provisions of this Agreement.

 

    6

     

    

 

Section 6.04 Modifications
and Amendments. The terms and provisions of this Agreement may be modified or amended only by written agreement executed by
all parties hereto.

 

Section 6.05 Waivers
and Consents. The terms and provisions of this Agreement may be waived, or consent for the departure therefrom granted, only
by a written document executed by the party entitled to the benefits of such terms or provisions. No such waiver or consent shall
be deemed to be or shall constitute a waiver or consent with respect to any other terms or provisions of this Agreement, whether
or not similar. Each such waiver or consent shall be effective only in the specific instance and for the purpose for which it
was given, and shall not constitute a continuing waiver or consent.

 

Section 6.06 Assignment.
The rights and obligations under this Agreement may not be assigned by either party hereto without the prior written consent of
the other party.

 

Section 6.07 Benefit.
All statements, representations, warranties, covenants and agreements in this Agreement shall be binding on the parties hereto
and shall inure to the benefit of the respective successors and permitted assigns of each party hereto. Nothing in this Agreement
shall be construed to create any rights or obligations except among the parties hereto, and no person or entity shall be regarded
as a third-party beneficiary of this Agreement.

 

Section 6.08 Governing
Law. This Agreement and the rights and obligations of the parties hereunder shall be construed in accordance with and governed
by the laws of the State of New York applicable to contracts wholly performed within the borders of such state, without giving
effect to the conflict of law principles thereof.

 

Section 6.09 Severability.
In the event that any court of competent jurisdiction shall determine that any provision, or any portion thereof, contained in
this Agreement shall be unreasonable or unenforceable in any respect, then such provision shall be deemed limited to the extent
that such court deems it reasonable and enforceable, and as so limited shall remain in full force and effect. In the event that
such court shall deem any such provision, or portion thereof, wholly unenforceable, the remaining provisions of this Agreement
shall nevertheless remain in full force and effect.

 

Section 6.10 No
Waiver of Rights, Powers and Remedies. No failure or delay by a party hereto in exercising any right, power or remedy under
this Agreement, and no course of dealing between the parties hereto, shall operate as a waiver of any such right, power or remedy
of such party. No single or partial exercise of any right, power or remedy under this Agreement by a party hereto, nor any abandonment
or discontinuance of steps to enforce any such right, power or remedy, shall preclude such party from any other or further exercise
thereof or the exercise of any other right, power or remedy hereunder. The election of any remedy by a party hereto shall not
constitute a waiver of the right of such party to pursue other available remedies. No notice to or demand on a party not expressly
required under this Agreement shall entitle the party receiving such notice or demand to any other or further notice or demand
in similar or other circumstances or constitute a waiver of the rights of the party giving such notice or demand to any other
or further action in any circumstances without such notice or demand.

 

    7

     

    

 

Section 6.11 Survival
of Representations and Warranties. All representations and warranties made by the parties hereto in this Agreement or in any
other agreement, certificate or instrument provided for or contemplated hereby, shall survive the execution and delivery hereof
and any investigations made by or on behalf of the parties.

 

Section 6.12 No
Broker or Finder. Each of the parties hereto represents and warrants to the other that no broker, finder or other financial
consultant has acted on its behalf in connection with this Agreement or the transactions contemplated hereby in such a way as
to create any liability on the other. Each of the parties hereto agrees to indemnify and holder the other harmless from any claim
or demand for commission or other compensation by any broker, finder, financial consultant or similar agent claiming to have been
employed by or on behalf of such party and to bear the cost of legal expenses incurred in defending against any such claim.

 

Section 6.13 Headings
and Captions. The headings and captions of the various subdivisions of this Agreement are for convenience of reference only
and shall in no way modify or affect the meaning or construction of any of the terms or provisions hereof.

 

Section 6.14 Counterparts.
This Agreement may be executed in one or more counterparts, all of which when taken together shall be considered one and the same
agreement and shall become effective when counterparts have been signed by each party and delivered to the other party, it being
understood that both parties need not sign the same counterpart. In the event that any signature is delivered by facsimile transmission
or any other form of electronic delivery, such signature shall create a valid and binding obligation of the party executing (or
on whose behalf such signature is executed) with the same force and effect as if such signature page were an original thereof.

 

Section 6.15 Construction.
The parties hereto have participated jointly in the negotiation and drafting of this Agreement. If an ambiguity or question of
intent or interpretation arises, this Agreement will be construed as if drafted jointly by the parties hereto and no presumption
or burden of proof will arise favoring or disfavoring any party hereto because of the authorship of any provision of this Agreement.
The words “include,” “includes” and “including” will be deemed to be followed by “without
limitation.” Pronouns in masculine, feminine, and neuter genders will be construed to include any other gender, and words
in the singular form will be construed to include the plural and vice versa, unless the context otherwise requires. The words
“this Agreement,” “herein,” “hereof,” “hereby,” “hereunder” and words
of similar import refer to this Agreement as a whole and not to any particular section unless expressly so limited. The parties
hereto intend that each representation, warranty, and covenant contained herein will have independent significance. If any party
hereto has breached any representation, warranty, or covenant contained herein in any respect, the fact that there exists another
representation, warranty or covenant relating to the same subject matter (regardless of the relative levels of specificity) which
such party hereto has not breached will not detract from or mitigate the fact that such party hereto is in breach of the first
representation, warranty, or covenant.

 

    8

     

    

 

Section 6.16 Mutual
Drafting. This Agreement is the joint product of the Subscriber and the Company and each provision hereof has been
subject to the mutual consultation, negotiation and agreement of such parties and shall not be construed for or against any
party hereto.

 

Article
VII.

Voting and Tender of Shares

 

The Subscriber agrees
to vote the Shares in favor of an initial business combination that the Company negotiates and submits for approval to the Company’s
stockholders and shall not seek redemption with respect to such Shares. Additionally, the Subscriber agrees not to tender any Shares
in connection with a tender offer presented to the Company’s stockholders in connection with an initial business combination
negotiated by the Company.

 

Article
VIII.

Indemnification

 

Each party shall indemnify
the other against any loss, cost or damages (including reasonable attorney’s fees and expenses) incurred as a result of such
party’s breach of any representation, warranty, covenant or agreement in this Agreement.

 

[Signature Pages Follow]

 

    9

     

    

 

If the foregoing accurately
sets forth our understanding and agreement, please sign the enclosed copy of this Agreement and return it to us.

 

	 	Very truly yours,
	 	 	 
	 	CAPITOL INVESTMENT CORP. VII
	 	 	 
	 	By:	/s/ L. Dyson Dryden
	 	Name: 	L. Dyson Dryden
	 	Title:	President and Chief Financial Officer

 

[Signature Page to Securities Subscription
Agreement]

 

     

     

    

 

Accepted and agreed as of the date first written above.

 

	 	CAPITOL ACQUISITION MANAGEMENT VII LLC
	 	 	 
	 	By:	/s/ Mark D. Ein
	 	Name: 	Mark D. Ein
	 	Title:	Managing Member

 

[Signature Page to Securities Subscription
Agreement]

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