Document:

EX-10.13

 Exhibit 10.13 

EXECUTIVE EMPLOYMENT AGREEMENT 

This Executive Employment Agreement (“Agreement”) is entered into as of June 22, 2011 (the “Effective Date”),
by and between Patriot National Insurance Group, Inc. (the “Company”), a corporation organized under the laws of Delaware, with its principal administrative office at 401 East Las Olas Boulevard, Suite 1650, Fort Lauderdale, Florida
33301, and Michael Grandstaff (“Executive”). 
 WHEREAS, the Company wishes to assure itself of the services or
continued services of Executive for the period provided in this Agreement; and 
 WHEREAS, Executive is willing to serve (or
continue to serve) in the employ of the Company on a full-time basis for said period. 
 NOW, THEREFORE, in consideration of
the mutual covenants herein contained, and upon the other terms and conditions hereinafter provided, the parties hereby agree as follows: 
  

	1.	Position and Responsibilities. The Company hereby employs Executive and Executive accepts employment as the Senior Vice President and Chief Financial Officer of the Company, on the terms and conditions herein set
forth. Executive shall have such duties, responsibilities and authority as is commensurate with his position and shall report to the Chief Executive Officer and the Board of Directors of the Company (the “Board”). Executive shall also
perform such other duties as may from time to time be assigned to Executive by the Chairman of the Board or the Board itself. During said period, Executive also agrees to serve, if elected, as an officer and director of any direct or indirect
subsidiary of the Company (individually, a “Subsidiary” or collectively, the “Subsidiaries”). 

  

	2.	Term. The period of Executive’s employment under this Agreement shall commence as of the Effective Date and shall continue for a period of 36 full calendar months thereafter (the “Initial Term”)
provided that such term shall be automatically extended for an additional 12-month period commencing at the end of the Initial Term, and successively thereafter for additional 12-month periods (each such period an “Additional Term”),
unless either party shall have given notice to the other party that such party does not desire to extend the term of this Agreement, such notice to be given at least 90 days prior to the end of the Initial Term or the applicable Additional Term (the
Initial Term and any Additional Terms, if applicable, collectively, the “Employment Term”). The date of expiration of the Employment Term shall be referred to herein as the “Termination Date.” 

 

	3.	 Extent of Services. During the term hereof, Executive shall devote his entire attention and energy to the business and affairs of the Company
and Subsidiaries on a full-time basis and shall not be engaged in any other business activity, regardless of whether such business activity is pursued for gain, profit or other pecuniary advantage, unless the Company otherwise consents; but this
shall not be construed as preventing Executive from investing his assets in such form or manner as will not require any services on the part of Executive in the operation of the affairs of the companies in which such investments are made and will
not otherwise conflict with the provisions of this Agreement. Full-time, as used above, shall mean a 40-hour work week, or such longer work week as the Board shall from time to time adopt.

	 	
The foregoing shall not be deemed to prevent Executive from participating in any charitable or not-for-profit organization to a reasonable extent, provided however that Executive does not receive
any salary or other remuneration from such charity or not-for-profit organization. Executive agrees to comply with all codes of conduct, personnel policies and procedures applicable to senior executives of the Company including, without limitation,
policies regarding sexual harassment, conflicts of interest and insider trading. 

  

	4.	Compensation. 

  

	 	(a)	Salary. During the term of this Agreement, the Company shall pay Executive an annual salary of not less than $350,000 (“Annual Salary”), payable in accordance with the Company’s regular payroll
procedures. During each year that this Agreement is in effect, the Company will review possible increases in Executive’s salary at least annually, with any such increases subject to the determination of the Board or the Compensation Committee
of the Board. 

  

	 	(b)	Bonus. Executive shall be eligible to receive an annual bonus in an amount as may be determined by the Board, pursuant to a bonus plan which may then be in effect or otherwise. Executive’s target bonus for
any fiscal year of the Company shall be up to 50% of Executive’s Annual Salary, subject to the attainment of such goals as the Board or Compensation Committee shall establish. 

 

	 	(c)	Business Expenses. Executive shall be entitled to prompt reimbursement for all reasonable expenses incurred by him in furtherance of the business of the Company in connection with Executive’s performance of
his duties hereunder, in accordance with the policies and procedures established for executive officers of the Company, and provided Executive properly accounts for such expenses. 

 

	 	(d)	Club Expenses. The Company shall pay up to $60,000 toward the initiation fee for Executive to become a member of one private country club, golf club, tennis club or similar club or association for business use
selected by Executive and approved by the Compensation Committee of the Board, which approval shall not be unreasonably withheld or delayed. The Company will also provide Executive with a gross-up payment so that such initiation fee payment (and any
gross-up payment) do not result in Executive incurring any net expense for taxes associated with such payment. The Company shall pay all annual or other periodic fees and dues for Executive to remain a member of such club. Fees and expenses under
this Section 4(d) are subject to an annual budget to be prepared by Executive and approved by the Compensation Committee. If Executive’s employment with the Company terminates within one year after the Effective Date for any reason other
than death, disability, resignation of Executive for Good Reason (as defined below) or termination without cause (as defined below), any amount paid by the Company for the initiation fee referenced above shall be reimbursed by the Executive to the
Company. 

  
 2 

	 	(e)	Vacation. Executive will be provided four weeks of vacation per calendar year, prorated based on date of hire, with additional weeks in accordance with the anniversary dates pursuant to the Company’s
vacation policy. 

  

	 	(f)	Relocation Expenses. The Company shall reimburse Executive for all reasonable moving expenses incurred or paid by Executive in relocating his current residence to Florida, including the brokerage commission on
the sale of Executive’s Michigan residence, subject to Executive providing reasonable substantiation and documentation as specified by the Company. The Company will provide Executive with a gross-up payment if necessary so that such
reimbursements (and any gross-up payment) do not result in Executive incurring any net expense for taxes associated with the reimbursement of moving expenses. In addition, the Company shall reimburse Executive’s temporary living expenses in Ft.
Lauderdale through June 30, 2008 (or such earlier date as Executive has obtained a new residence in Florida). 

  

	 	(g)	Automobile Allowance. During the Employment Term, the Company shall pay or provide Executive an automobile allowance of $1,000 per month in accordance with policies established by the Company from time to time.

  

	 	(h)	Other Benefits. Executive shall be entitled to participate in all medical and other employee plans of the Company, if any, on the same basis as other executives of the Company, subject in all cases to the
respective terms of such plans. 

  

	5.	Termination. 

  

	 	(a)	Death. This Agreement and Executive’s employment hereunder shall terminate immediately upon Executive’s death. In such event, the Company shall be obligated to pay only Executive’s salary to the
date of Executive’s death and any earned but unpaid bonus with respect to any calendar year ended prior to the date of termination. 

  

	 	(b)	Incapacity. To the extent permitted by law, if Executive is absent from his employment for reasons of illness or other physical or mental incapacity which renders Executive unable to perform the essential
functions of his position, with or without reasonable accommodation, for more than an aggregate of 90 days, whether or not consecutive, in any period of twelve consecutive months, then upon at least 60 days’ prior written notice to
Executive, if such is consistent with applicable law, the Company may terminate this Agreement and Executive’s employment hereunder, unless, within that notice period, Executive shall have resumed performance of the essential functions of his
positions, with or without reasonable accommodation. 

  

	 	(c)	Termination by the Company. 

  

	 	(i)	Termination for Cause. The Company may terminate this Agreement and Executive’s employment hereunder at any time for Cause. As used herein, “Cause” shall mean: 

  
 3 

	 	(A)	a material breach by Executive of Executive’s duties and obligations hereunder, including but not limited to gross negligence in the performance of his duties and responsibilities or the willful failure to follow
the Board’s directions; provided, however, that Cause shall not exist unless the Company has provided Executive with written notice setting forth the existence of the non-performance, failure or breach and Executive shall not have cured same
within 30 days after receiving such notice; 

  

	 	(B)	willful misconduct by Executive which in the reasonable determination of the Board has caused or is likely to cause material injury to the reputation or business of the Company; 

 

	 	(C)	any act of fraud, material misappropriation or other dishonesty by Executive; or 

  

	 	(D)	Executive’s conviction of a felony. 

 Executive shall be considered to have been
discharged for Cause if the Company determines within 30 days after his resignation or discharge that discharge for Cause was warranted. In the event of termination for Cause, the Company shall be obligated to pay Executive only
Executive’s salary up to the date of termination and any earned but unpaid bonus with respect to any calendar year ended prior to the date of termination. 
  

	 	(ii)	Termination Without Cause. 

  

	 	(A)	Notwithstanding anything contained herein to the contrary, the Company also may terminate this Agreement and Executive’s employment hereunder for reason other than death, incapacity or cause upon no less than 60
days’ prior written notice to Executive. The Company shall be deemed to have terminated this Agreement without cause in the event that this Agreement is terminated as a result of the Company’s giving notice of non-renewal prior to the end
of the initial term or any additional term as provided in Section 2 above. In the event that the Company terminates this Agreement pursuant to the provisions of this Section 5(c)(ii), Executive shall be entitled to receive a severance
payment equal to 100% of Executive’s Annual Salary at the time of termination (the “Severance Payment”). Subject to Section 10 hereof, the Severance Payment shall be payable in a series of 12 monthly installments commencing on
the first day of the month following the date of termination. If for any reason any court determines that any of the restrictions contained in Section 8 hereof are not enforceable, the Company shall have no obligation to pay the Severance
Payment or any remaining installment thereof to Executive. The Company agrees that it will not petition any court to determine that any of the restrictions contained in Section 8 hereof are not enforceable in order to avoid the obligation to
pay the Severance Payments referenced above. 

  
 4 

	 	(B)	If the Company is obligated by law (including the WARN Act or any similar state or foreign law) to pay Executive severance pay, a termination indemnity, notice pay, or the like, then the amount of such legally required
pay shall reduce the Severance Payment hereunder. 

  

	 	(C)	Notwithstanding anything herein to the contrary, the payment of any Severance Payments hereunder to Executive shall be subject to the execution by Executive (and failure to revoke) of a general release of the Company
and its affiliates of any and all claims under this Agreement or related to or arising out of Executive’s employment hereunder, in a form and manner satisfactory to the Company and Executive. 

 

	 	(D)	Executive will not be entitled to receive Severance Payments under this Section 5(c)(ii) in the event that this Agreement is terminated as a result of the Company’s giving notice of non-renewal prior to the
end of the Initial Term or any Additional Term as provided in Section 2 above. 

  

	 	(E)	In the event of termination by the Company without Cause, the Company shall be obligated to pay Executive only Executive’s salary up to the date of termination and any earned but unpaid bonus with respect to any
calendar year ended prior to the date of termination. 

  

	 	(d)	Termination by Executive Without Good Reason. Executive may terminate this Agreement and his employment hereunder for any reason whatsoever, upon no less than 120 days’ prior written notice to the Company.
In the event that Executive terminates this Agreement pursuant to the provisions of this Section 5(d) without “Good Reason” as hereinafter defined, the Company shall be obligated to pay Executive only Executive’s salary up to the
date of termination and any earned but unpaid bonus with respect to any calendar year ended prior to the date of-termination. 

  

	 	(e)	Termination by Executive For Good Reason. If Executive resigns for Good Reason, then Executive’s termination shall be treated as a termination by the Company without Cause pursuant to Section 5(c)(ii)
hereof. As used herein, a resignation for “Good Reason” shall mean a resignation by Executive within 90 days following the initial existence of one or more of the following conditions arising without Executive’s consent:

  

	 	(i)	a material reduction in Executive’s Annual Salary; 

  

	 	(ii)	a material diminution in Executive’s authority, duties, or responsibilities; 

  
 5 

	 	(iii)	a relocation of Executive’s principal place of employment by more than 50 miles from its location at the Effective Date of this Agreement; or 

 

	 	(iv)	any other action or inaction that constitutes a material breach by the Company of this Agreement; 

provided, however, that Good Reason shall not exist unless Executive has provided the Company with a written notice setting forth the
reason(s) for the existence of Good Reason within 30 days of the initial existence of the condition(s), and the Company has not cured the reason(s) for the existence of Good Reason within 30 days after receiving such notice. 

 

	6.	Change in Control. 

  

	 	(a)	Change in Control Severance Compensation. If within twelve months following a Change in Control (as defined below) Executive’s employment with the Company is terminated by the Company without Cause or
Executive resigns for Good Reason, then Executive shall be entitled to terminate this Agreement and employment hereunder and receive from the Company a payment equal to 200% of the amount of the Severance Payment specified in Section 5(c)(ii)
or 5(e) of this Agreement (the “Change in Control Compensation”). Subject to Section 10 hereof, the Change in Control Compensation shall be payable in 12 monthly installments commencing on the first day of the month following the date
of termination. If for any reason any court determines that any of the restrictions contained in Section 8 hereof are not enforceable, the Company shall have no obligation to pay the Change in Control Compensation or any remaining installment
thereof to Executive. The Company agrees that it will not petition any court to determine that any of the restrictions contained in Section 8 hereof are not enforceable in order to avoid the obligation to pay the Change of Control Compensation
referenced above. 

  

	 	(b)	Change in Control. For purposes of this Agreement, “Change in Control” shall mean the occurrence of any of the following events: 

 

	 	(i)	the date any one person, or more than one “person” acting as a group, acquires (or has acquired during the twelve month period ending on the date of the most recent acquisition by such person(s)) ownership of
common stock possessing 51% or more of the total voting power of the common stock of the Company; 

  

	 	(ii)	individuals who at any time during the term of this Agreement constitute the board of directors of the Company (the “Incumbent Board”) cease for any reason to constitute at least a majority thereof, provided
that any person becoming a director subsequent to the date hereof whose election or nomination for election was approved by a vote of at least three-quarters of the directors comprising the Incumbent Board
(either by a which such person is named as a nominee for director, without objection to such nomination) shall be, for purposes of this clause (ii) considered as though such person were a member of the Incumbent Board; 

  
 6 

	 	(iii)	any consolidation or merger to which the Company is a party, if following such consolidation or merger, stockholders of the Company immediately prior to such consolidation or merger shall not beneficially own securities
representing at least 51% of the combined voting power of the outstanding voting securities of the surviving or continuing corporation; or 

  

	 	(iv)	any sale, lease, exchange or other transfer (in one transaction or in a series of related transactions) of all, or substantially all, of the assets of the Company, other than to an entity (or entities) of which the
Company or the stockholders of the Company immediately prior to such transaction beneficially own securities representing at least 51% of the combined voting power of the outstanding voting securities. 

 

	 	(c)	Nonduplication of Benefits. If Executive receives any Change in Control Compensation under this Section 6, he or she shall not be entitled to receive any Severance Payments under Section 5(c)(ii) or
5(e) hereof. 

  

	 	(d)	General Release. Notwithstanding anything herein to the contrary, the payment of any Change in Control Compensation hereunder to Executive shall be subject to the execution by Executive (and failure to revoke) of
a general release of the Company and its affiliates of any and all claims under this Agreement or related to or arising out of Executive’s employment hereunder, in a form and manner satisfactory to the Company and Executive. 

 

	7.	Tax and Other Restrictions. Notwithstanding anything herein to the contrary: 

  

	 	(a)	Excess Parachute Payments. In the event that payment of any amount under this Agreement, including, but not limited to, any Severance Payment under Section 5(c)(ii) or 5(e) or Change in Control Compensation
under Section 6, would cause Executive to be the recipient of an excess parachute payment within the meaning of section 280G(b) of the Code, the amount of the payments to be made to Executive pursuant to this Agreement shall be reduced to an
amount equal-to-299% of-Executive’s ‘‘base amount’’-within-the meaning-of Code section 280G. The manner in which such reduction occurs, including the items of payment and amounts thereof to be reduced, shall be determined by
the Company. 

  

	 	(b)	Payments in Excess of $1 Million. If any payment hereunder, including but not limited to, a Severance Payment under Section 5(c)(ii) or 5(e) or Change in Control Compensation under Section 6, would not
be deductible by the Company for federal income tax purposes by reason of Code section 162(m), or any similar or successor statute (excluding Code section 280G), such payment shall be such payment shall be deductible by the Company.

  

	8.	Covenants of the Executive. 

  

	 	(a)	 Nonsolicitation. During the Employment Term and for a period of one year thereafter, Executive shall not, directly or indirectly,
(i) employ, solicit for employment or otherwise contract for the services of any individual who is or was an employee of the Company or any of its Subsidiaries during the 

  
 7 

	 	
Employment Term; (ii) otherwise induce or attempt to induce any employee of the Company or its Subsidiaries to leave the employ of the Company or such Subsidiary, or in any way knowingly
interfere with the relationship between the Company or any such Subsidiary and any employee respectively thereof, provided, however, that this clause (ii) shall not prohibit the activities described in the preceding clause (i) following
termination of the Employment Term with respect to any individual who was not an employee of the Company or its Subsidiaries during the Employment Term; or (iii) induce or attempt to induce any customer, supplier, broker, agent, licensee or
other business relation of the Company or any Subsidiary of the Company to cease doing business with the Company or such Subsidiary, or interfere in any way with the relationship between any such customer, supplier, broker, agent, licensee or
business relation and the Company or any subsidiary thereof. 

  

	 	(b)	Nondisclosure. For the Employment Term and thereafter, (i) Executive shall not divulge, transmit or otherwise disclose (except as legally compelled by court order, and then only to the extent required, after
prompt notice to the Company’s Chief Executive Officer and Chief Legal Officer of any such order), directly or indirectly, other than in the regular and proper course of business of the Company and its Subsidiaries, any confidential knowledge
or information with respect to the operations or finances of the Company or any of its Subsidiaries or with respect to confidential or secret processes, methods, services, techniques, reinsurance arrangements, customers or plans with respect to the
Company or its Subsidiaries and (ii) Executive will not use, directly or indirectly, any confidential information for the benefit of anyone other than the Company and its Subsidiaries; provided, however, that Executive has no obligation,
express or implied, to refrain from using or disclosing to others any knowledge or information which is or hereafter shall become available to the general public other than through disclosure by Executive or requested by regulatory bodies or as
required by judicial courts. All new processes, techniques, know-how, methods, inventions, plans, products, patents and devices developed, made or invented by Executive, alone or with others, while an employee of the Company which are related to the
business of the Company and its Subsidiaries shall be and become the sole property of the Company, unless released in writing by the Board, and Executive hereby assigns any and all rights therein or thereto to the Company. 

 

	 	(c)	Nondisparagement. During the Employment Term and thereafter, Executive shall not take any action to disparage or criticize the Company or its Subsidiaries or their respective employees, directors, owners or
customers or to engage in any other action that injures or hinders the business relationships of the Company or its Subsidiaries. During the Employment Term and thereafter, the Company shall not take any action to disparage or criticize Executive to
any third parties. Nothing contained in this Section 8(c) shall preclude either Executive or the Company from (i) making truthful statements or disclosures that are required by applicable law, regulation or legal process or
(ii) enforcing their respective rights under this Agreement. 

  

	 	(d)	 Noncompetition. In consideration of the payment to Executive of the Severance payments pursuant to Section 5(c)(ii) or 5(e) or Change in
Control 

  
 8 

	 	
Compensation pursuant to Section 6, Executive hereby agrees that, from and after the Termination Date, and for 12 months thereafter, Executive shall not participate as a partner, joint
venturer, proprietor, shareholder, employee or consultant, or have any other direct or indirect financial interest (other than a less than 10% interest in a corporation whose shares are regularly traded on a national securities exchange or in the
over-the-counter market), including, without limitation, the interest of a creditor in any form, in, or in connection with, any business competing directly or indirectly with the business of the Company and its Subsidiaries in any geographic area
where the Company and its Subsidiaries are actively engaged in conducting business as of the Termination Date. The purpose of this restrictive covenant is to protect the Company’s trade secrets and other confidential information, including,
without limitation, its business plans, processes and customer information. 

  

	 	(e)	Return of Company Property. All files, records, correspondence, memoranda, notes or other documents (including, without limitation, those in computer readable form) or property relating or belonging to the
Company or its Subsidiaries or affiliates, whether prepared by Executive or otherwise coming into Executive’s possession in the course of the performance of his services under this Agreement, shall be the exclusive property of the Company and
shall be delivered to the Company, and not retained by Executive (including without limitations, any copies thereof), promptly upon request by the Company and, in any event, within 60 days following the Termination Date. 

 

	 	(f)	Scope. The Company and Executive further acknowledge that the time, scope, geographic area and other provisions of this Section 8 have been specifically negotiated by sophisticated commercial parties and
agree that all such provisions are reasonable under the circumstances of the activities contemplated by this Agreement. In the event that the agreements in this Section 8 shall be determined by any court of competent jurisdiction to be
unenforceable by reason of their extending for too great a period of time or over too great a geographical area or by reason of their being too extensive in any other respect, they shall be interpreted to extend only over the maximum geographical
area as to which they may be enforceable and/or to the maximum extent in all other respect as to which they may be enforceable, all as determined by such court in such action. 

 

	 	(g)	Enforcement. Both parties recognize that the services to be rendered under this Agreement by Executive are special, unique and of extraordinary character and that in the event of the breach by Executive of any of
the terms and conditions of this Section 8 to be performed by him, then the Company shall be entitled, if it so elects, to institute and prosecute proceedings in any court of competent jurisdiction, either in law or in equity, to obtain damages
for any breach hereof, or to enforce the specific performance hereof by Executive or to enjoin Executive from performing acts prohibited above during the period herein covered, but nothing herein contained shall be construed to prevent such other
remedy in the courts as the Company may elect to invoke. 

  
 9 

	 	(h)	Other. If Executive competes with the Company or otherwise violates any of the restrictions contained in this Section 8, the Company shall have no obligation to pay the Severance Payment or Change of Control
Compensation or any remaining installment thereof to Executive. 

  

	9.	Indemnification. The Company shall provide Executive (including Executive’s heirs, executors and administrators) with coverage under a standard directors’ and officers’ liability insurance policy
at its expense, and shall indemnify Executive (and Executive’s heirs, executors and administrators) to the fullest extent permitted under Delaware law against all expenses and liabilities reasonably incurred by Executive in connection with or
arising out of any action, suit or proceeding in which Executive may be involved by reason of Executive’s having been a director or officer of the Company (whether or not Executive continues to be a director or officer at the time of incurring
such expenses or liabilities), such expenses and liabilities to include, but not be limited to, judgments, court costs and attorneys’ fees and the cost of reasonable settlements. 

 

	10.	Application of Code Section 409A. 

  

	 	(a)	General. To the extent applicable, it is intended that this Agreement comply with the provisions of Code section 409A, so as to prevent inclusion in gross income of any amounts payable or benefits provided
hereunder in a taxable year that is prior to the taxable year or years in which such amounts or benefits would otherwise actually be distributed, provided or otherwise made available to Executive. This Agreement shall be construed, administered, and
governed in a manner consistent with this intent and the following provisions of this Section shall control over any contrary provisions of this Agreement. 

  

	 	(b)	Restrictions on Specified Employees. In the event Executive is a “specified employee” within the meaning of Code section 409A(a)(2)(B)(i) and delayed payment of any amount or commencement of any benefit
under this Agreement is required to avoid a prohibited distribution under Code section 409A(a)(2), then amounts payable in connection with Executive’s termination of employment will be delayed and paid, with interest at the short term
applicable federal rate as in effect as of the termination date, in a single lump sum six months thereafter (or if earlier, the date of Executive’s death); provided, however, that payments to which Executive is entitled under
Section 5(c)(ii), 5(e) and 6(a) of this Agreement need not be delayed under this Section 10(b) to the extent those payments would comply with the requirements of 1.409A-1(a)(b)(9), which generally requires that such payments not exceed two
times the lesser of (1) Executive’s annualized compensation based on his annual rate of pay in the year before the date of termination or (2) the Code section 401(a)(17) limit applicable to qualified plans during the year of
Executive’s date of termination. 

  

	 	(c)	Separation from Service. Payments and benefits hereunder upon Executive’s termination or severance of employment with the Company that constitute deferred compensation under Code section 409A payable shall
be paid or provided only at the time of a termination of Executive’s employment which constitutes a “separation from service” within the meaning of Code section 409A (subject to a possible six-month delay pursuant to the subsection
(b) above). 

  
 10 

	 	(d)	Installment Payments. For purposes of Code section 409A, the right to a series of payments under this Agreement shall be treated as a right to a series of separate payments so that each payment hereunder is designated
as a separate payment for purposes of Code section 409A. 

  

	 	(e)	Reimbursements. All reimbursements and in kind benefits provided under this Agreement, including, but not limited to, payments under Sections 4(c) and 9, shall be made or provided in accordance with the
requirements of Code section 409A, including, where applicable, the requirement that (i) any reimbursement is for expenses incurred during Executive’s lifetime (or during a shorter period of- time
specified in this Agreement), (ii) the amount of expenses eligible for reimbursement, or in kind benefits provided, during a calendar year may not affect the expenses eligible for reimbursement, or in kind benefits to be provided, in any other
calendar year, (iii) the reimbursement of an eligible expense will be made on or before the last day of the calendar year following the year in which the expense is incurred, and (iv) the right to reimbursement or in kind benefits is not
subject to liquidation or exchange for another benefit. 

  

	 	(f)	References to Code Section 409A. References in this Agreement to Code section 409A include both that section of the Code itself and any guidance promulgated thereunder. 

 

	11.	Miscellaneous. 

  

	 	(a)	Modification. This Agreement may not be modified or amended except by an instrument in writing signed by the parties hereto. 

  

	 	(b)	Waiver. No term or condition of this Agreement shall be deemed to have been waived, nor shall there be any estoppel against the enforcement of any provision of this Agreement, except by written instrument of the
party charged with such waiver or estoppel. No such written waiver shall be deemed a continuing waiver unless specifically stated therein, and each such waiver shall operate only as to the specific term or condition waived and shall not constitute a
waiver of such term or condition for the future as to any act other than that specifically waived. 

  

	 	(c)	Notices. Any notice required or permitted to be given under this Agreement shall be sufficient if in writing and if sent by registered or certified mail to Executive or the Company at the address set forth below
or to such other address as they shall notify each other in writing: 

 If to the Company: 

Patriot National Insurance Group, Inc. 

401 East Las Olas Boulevard, Suite 1540 

Fort Lauderdale, Florida 33301 

  
 11 

 If to Executive: 

To the last mailing address on file with the Company. 
  

	 	(d)	Assignment. This Agreement shall be binding upon and inure to the benefit of the Company and its successors and permitted assigns and Executive and personal representatives, heirs, legatees and beneficiaries.
This Agreement may be assigned by the Company with the consent of Executive to a fiscally responsible entity that assumes the obligations set forth herein, but shall not be assignable by Executive. 

 

	 	(e)	Applicable Law. This Agreement shall be construed in accordance with the laws of the State of Florida in every respect, including, without limitation, validity, interpretation and performance. Any dispute between
the parties hereto, arising under or relating to this Agreement (as hereinafter defined), or Executive’s employment with the Company, other than for an action by the Company for specific performance, injunction or other equitable remedy to
enforce Section 8 hereof shall be settled by arbitration in Fort Lauderdale, Florida in accordance with the then applicable rules of the American Arbitration Association. The prevailing party may be awarded in such arbitration its reasonable
attorneys’ fees and expenses, and judgment upon the award rendered may be entered in any court having jurisdiction thereof. 

  

	 	(f)	Headings. Section headings and numbers herein are included for convenience of reference only and this Agreement is not to be construed with reference thereto. If there be any conflict between such numbers and
headings and the text hereof, the text shall control. 

  

	 	(g)	Severability. If for any reason any portion of this Agreement shall be held invalid or unenforceable, it is agreed that the same shall not affect the validity or enforceability of the remainder hereof. The
portion of the Agreement which is not invalid or unenforceable shall be considered enforceable and binding on the parties and the invalid or unenforceable provision(s), clause(s) or sentence(s) shall be deemed excised, modified or restricted to the
extent necessary to render the same valid and enforceable and this Agreement shall be construed as if such invalid or unenforceable provision(s), clause(s), or sentences(s) were omitted. The provisions of this Section 11(g), as well as Sections
8 and 9 hereof, shall survive the termination of this Agreement. 

  

	 	(h)	Entire Agreement. This Agreement contain the entire agreement of the parties with respect to its subject matter and supersedes all previous agreements between the parties. No officer, employee, or representative
of the Company has any authority to make any representation or promise in connection with this Agreement or the subject matter thereof that is not contained therein, and Executive represents and warrants he has not executed this Agreement in
reliance upon any such representation or promise. No modification of this Agreement shall be valid unless made in writing and signed by the parties hereto. 

  
 12 

	 	(i)	Waiver of Breach. The waiver by either party of a breach of any provision of this Agreement by the other party shall not operate or be construed as a waiver of any subsequent breach by the breaching party.

  

	 	(j)	Counterparts. This Agreement may be executed in one or more counterparts, each of which shall be deemed to be an original, but all of which together shall constitute one agreement. 

IN WITNESS WHEREOF, the Company has caused this Agreement to be executed by its duly authorized officer and Executive has signed this
Agreement all on the day and year first above written. 
  

			
	 PATRIOT NATIONAL INSURANCE

GROUP, INC.

		 	a Delaware corporation
		
	By:	 	 /s/ Steve Mariano

		 	Title: CEO & Chairman
	
	EXECUTIVE
	
	 /s/ Michael Grandstaff

	Michael Grandstaff

  
 13 

 ASSIGNMENT AND ASSUMPTION OF EMPLOYMENT AGREEMENT 

THIS ASSIGNMENT AND ASSUMPTION OF EMPLOYMENT AGREEMENT (the “Assignment Agreement”) is entered into as of
December 10, 2014 by and between Guarantee Insurance Group, Inc. f/k/a Patriot National Insurance Group, Inc., a corporation organized under the laws of Delaware (the “Assignor”), Patriot National, Inc., a corporation organized
under the laws of Delaware (the “Assignee”) and Michael Grandstaff (the “Executive”). 

WHEREAS, the Assignor is a party to an employment agreement with the Executive, dated as of June 22, 2011, as amended, modified or
supplemented from time to time, (the “Employment Agreement”); 
 WHEREAS, the Employment Agreement provides that the
Assignor may, with the consent of Executive, assign its obligations under the Employment Agreement to a fiscally responsible entity that assumes the obligations set forth in the Employment Agreement;  

WHEREAS, the Assignor desires to assign, and the Assignee desires to assume, all of the Assignor’s rights and obligations under
the Employment Agreement; 
 WHEREAS, Executive hereby consents to the Assignor’s assignment of all of its rights and
obligations under the Employment Agreement to the Assignee; and 
 WHEREAS, the Assignor, the Assignee and the Executive
desire to amend certain provisions of the Employment Agreement; 
 NOW, THEREFORE, in consideration of the mutual promises contained
herein and for other good and valuable consideration, the receipt and sufficiency of which is hereby acknowledged, the parties agree as follows: 
  

	 	1.	Effective as of the date hereof, (i) the Assignor hereby assigns, transfers and conveys to Assignee, and Assignee hereby accepts the assignment of, all rights and obligations with respect to the Employment
Agreement and (ii) the Assignor is hereby discharged of any and all of its obligations under the Employment Agreement (together, the “Transfer”). 

 

	 	2.	Executive hereby consents to the Transfer for purposes of Section 11(d) of the Employment Agreement. 

  

	 	3.	Effective as of the date hereof, the provisions of the Employment Agreement shall be deemed to be amended, mutatis mutandis, to give effect to the Transfer, including (without limitation) that: 

 

	 	a.	notwithstanding Section 1 of the Employment Agreement, Executive’s title shall be Executive Vice President, Strategic Planning & Acquisitions of Patriot National, Inc. and Executive shall report to
the Chief Executive Officer and Executive shall perform duties commensurate with his position; and 

  

	 	b.	all references to “the Company” in the Employment Agreement shall be deemed to refer to the Assignee. 

	 	4.	Effective as of the date hereof, the Employment Agreement is hereby amended and modified as follows: 

  

	 	a.	Section 7(a) of the Employment Agreement shall be modified by inserting the words “or otherwise” after the phrase “this Agreement” in the two instances where such phrase appears therein. For
illustrative purposes, the foregoing modifications are marked in the excerpt text below. 

 “Excess Parachute
Payments. In the event that payment of any amount under this Agreement or otherwise, including, but not limited to, any Severance Payment under Section 5(c)(ii) or 5(e) or Change in Control Compensation under Section 6,
would cause Executive to be the recipient of an excess parachute payment within the meaning of Code Section 280G(b), the amount of the payments to be made to Executive pursuant to this Agreement or otherwise shall be reduced to an
amount equal to 299% of Executive’s “base amount” within the meaning of Code Section 280G. The manner in which such reduction occurs, including the items of payment and amounts thereof to be reduced, shall be determined by the
Company.” 
  

	 	b.	Section 7(b) of the Employment Agreement shall be modified by (i) deleting the word “time” and inserting the phrase ““permissible payment event” (within the meaning of Code section
409A)” in replacement thereof and (ii) deleting the third instance of the word “shall” and inserting the word “would” in replacement thereof. For illustrative purposes, the foregoing modifications are marked in the
excerpt text below. 

 “Payments in Excess of $1 Million. If any payment hereunder, including but not limited to,
a Severance Payment under Section 5(c)(ii) or 5(e) or Change in Control Compensation under Section 6, would not be deductible by the Company for federal income tax purposes by reason of Code Section 162(m), or any similar or successor
statute (excluding Code Section 280G), such payment shall be deferred and the amount thereof shall be paid to Executive at the earliest “permissible payment event” (within the meaning of Code section 409A)
time that such payment would shall be deductible by the Company.” 
  

	 	5.	Except as expressly amended or modified by this Assignment Agreement, all other terms and provisions of the Employment Agreement shall continue in full force and effect. 

 

	 	6.	This Assignment Agreement may not be altered, modified, or amended except by written instrument signed by the parties hereto. This Assignment Agreement shall be governed by and construed in accordance with the laws of
the State of Florida, without regard to conflicts of laws principles thereof. This Assignment Agreement will inure to the benefit of and bind the respective successors of the parties hereto. 

 

	 	7.	This Assignment Agreement may be executed in one or more counterparts, each of which when executed shall be deemed to be an original but all of which when taken together shall constitute one and the same agreement.
Notwithstanding the date of execution of any counterpart, each counterpart shall be deemed to bear the date first written above. 

  
 2 

 [Signature pages follow] 

  
 3 

 IN WITNESS WHEREOF, this Assignment and Assumption of Employment Agreement has been duly executed
and delivered as of the date first above written. 
  

					
	GUARANTEE INSURANCE GROUP, INC.
		
	By:	 	 /s/ David A Skup

		 	Name:	 	David A Skup
		 	Title:	 	Assistant Treasurer
	
	PATRIOT NATIONAL, INC.
		
	By:	 	 /s/ Christopher A. Pesch

		 	Name:	 	Christopher A. Pesch
		 	Title:	 	Executive Vice President &
		 		 	General Counsel

  
 4 

 IN WITNESS WHEREOF, this Assignment and Assumption of Employment Agreement has been duly executed
and delivered as of the date first above written. 
  

	
	   /s/ Michael Grandstaff

	Michael Grandstaff

  
 5EX-10.14

 Exhibit 10.14 

EXECUTIVE EMPLOYMENT AGREEMENT 

This Executive Employment Agreement (“Agreement”) is entered into as of September 8, 2014 (the “Effective Date”), by
and between Old Guard Risk Services, Inc. (the “Company”), a corporation organized under the laws of Delaware, with principal administrative offices at 401 East Las Olas Boulevard, Suite 1650, Fort Lauderdale, Florida 33301, and
Christopher A. Pesch (“Executive”). 
  

	1.	Position and Responsibilities. The Company hereby employs Executive and Executive accepts employment in the following position: Executive Vice President, General Counsel and Chief Legal Officer. Executive shall
have such duties, responsibilities and authority as is commensurate with the positions set forth above and, in all instances shall report to the Chief Executive Officer and the Board. 

Executive shall also perform such other duties as may from time to time be assigned to Executive by the Chairman of the Board or by the Board
itself. Executive also agrees to serve, if elected, as an officer and director of any direct or indirect subsidiary of the Company (individually, a “Subsidiary” or collectively, the “Subsidiaries”). 

 

	2.	Term. The period of Executive’s employment under this Agreement shall commence as of the Effective Date and shall continue until December 31, 2017 (the “Initial Term”). The Initial term shall
be automatically extended for an additional 12-month period commencing at the end of the Initial Term, and successively thereafter for additional 12-month periods (each such period an “Additional Term”), unless either party gives written
notice to the other party that such party does not desire to extend the term of this Agreement. Written notice to not continue with another Additional Term must be given at least ninety (90) days prior to the end of the Initial Term or the
applicable Additional Term (the Initial Term and any Additional Terms, if applicable, collectively, the “Employment Term”). In the event a Change in Control (as defined below) occurs on or after the Effective Date, the Employment Term
shall be extended and continue in effect until at least the second anniversary of such Change in Control. The date of expiration of the Employment Term shall be referred to herein as the “Termination Date.” Upon the Termination Date,
Executive shall be deemed to resign from any positions held as of such date. Executive also shall be deemed to resign from the board of directors of the Company or any Subsidiary to which he has been appointed or nominated by or on behalf of the
Company and any fiduciary positions with respect to the employee benefit plans of the Company or any Subsidiary. 

  

	3.	 Extent of Services. During the Employment Term, Executive shall devote his entire attention and energy to the business and affairs of the
Company and Subsidiaries on a full-time basis and shall not be engaged in any other business activity, regardless of whether such business activity is pursued for gain, profit or other pecuniary advantage, that interferes with the business of the
Company, but this shall not be construed as preventing Executive from investing his assets in such form or manner as will not require any services on the part of Executive in the operation of the affairs of the companies in which such investments
are made and will not otherwise conflict with the provisions of this Agreement. Provided however, The Company understands that Executive may 

	 	
provide transitioning legal services to persons or entities that were former clients of Executive so long as such services do not conflict with Executive’s duties to the Company as outlined
herein. 

 Executive may devote reasonable time to activities such as supervision of personal investments and activities
involving professional, charitable, educational, religious, and similar types of activities, speaking engagements and membership on other boards of directors, provided such activities do not interfere materially with the business of the Company. The
time involved in such activities will not be treated as vacation time. Executive will be entitled to keep any amounts paid to him in connection with such activities (e.g., director fees and honoraria). Full-time, as used above, shall mean a
40-hour workweek, or such longer workweek, as the Board shall from time to time adopt. Executive agrees to comply in all material respects with all codes of conduct, personnel policies and procedures applicable to senior executives of the Company
including, without limitation, policies regarding sexual harassment, conflicts of interest and insider trading. 
  

	4.	Compensation. 

  

	 	(a)	Salary. During the Employment Term, the Company shall pay Executive an annual salary of not less than $435,000 (“Annual Salary”), payable in accordance with the Company’s regular payroll
procedures. The Company shall review possible increases in Executive’s salary on an annual basis with such review occurring not later than March 31st of such year with any such increases
subject to the determination of the Board or the Compensation Committee of the Board. Annual Salary shall not be decreased without Executive’s prior written consent, and the term “Annual Salary” for purposes of this Agreement shall
refer to base salary annualized, as most recently increased. 

  

	 	(b)	Bonus. During the Employment Term, Executive shall be eligible to receive an annual bonus in an amount determined by the Compensation Committee or the Board, pursuant to a bonus plan that may then be in effect or
otherwise, subject to the attainment of such goals as the Compensation or Committee the Board shall establish and communicate to Executive within the first ninety (90) days of such fiscal year. It is the intent of the Company that any annual
bonus shall be paid no later than 2 1/2 months following the end of the calendar year (or, if later, the Company’s tax year) in which
or within which the applicable fiscal year ends and as subject to approval by the Board of Directors. 

  

	 	(c)	Business Expenses. During the Employment Term, Executive shall be entitled to prompt reimbursement for all reasonable expenses, including but not limited to first class travel expenses and expenses incurred in
complying with legal continuing education requirements in Illinois and Washington State, incurred by him in furtherance of the business of the Company in connection with Executive’s performance of his duties hereunder, in accordance with the
policies and procedures established for executive officers of the Company, and provided Executive properly accounts for such expenses. 

  
 2 

	 	(d)	Vacation. During the Employment Term, Executive will be provided four weeks of vacation per calendar year, prorated based on date of hire, with additional weeks in accordance with the anniversary dates pursuant
to the Company’s vacation policy. 

  

	 	(e)	Long Term Incentive and Equity Compensation. During the Employment Term, Executive shall be entitled to participate in, and receive awards under, any long-term incentive plan (whether payable in cash, equity or
otherwise) maintained by the Company in which other senior executives of the Company participate, in the discretion of the Compensation Committee of the Board. 

  

	 	(f)	Other Benefits. During the Employment Term, Executive shall be entitled to participate in all benefit plans offered by the Company including, without limitation, medical, dental, short-term and long-term
disability, life, pension, profit sharing and nonqualified deferred compensation arrangements, as the Board may determine in its discretion on the same basis as other executives of the Company, subject in all cases to the respective terms of such
plans. The Company reserves the right to modify, suspend or discontinue any and all of the plans, practices, policies and programs at any time without recourse by the Executive, so long as the Company takes such action generally with respect to all
other similarly situated executive officers. 

  

	 	(g)	Club Expenses. During the Employment Term, the Company shall pay the initiation fee and membership expenses for Executive to become and remain a full member of a private club of executive’s choosing (full
membership to include golf, tennis, fitness, and social facilities). The Company shall also provide Executive with a gross-up payment so that such initiation fee payment (and any gross-up payment) does not result in Executive incurring any net
expenses for taxes associated with such payment. The Company shall pay all annual or other periodic fees and dues for Executive to remain a member of such club. If Executive resigns from employment without Good Reason (as defined below), within one
year of the Effective Date, any amount paid by the Company for the initiation fee referenced above shall be reimbursed by the Executive. 

  

	 	(h)	Automobile Allowance. During the Employment Term, the Company shall provide Executive an automobile allowance of $1,500 per month, the amount of which shall be a gross-up payment such that payment of the
allowance does not result in Executive incurring any taxes associated with such allowance. 

  

	 	(i)	Signing Bonus. Within ten days of the Effective date, the Company shall pay employee a signing bonus of $200,000. 

  

	 	(j)	Special Bonus. Company shall pay Executive a one-time, special bonus of $300,000 on July 1, 2015. 

  

	 	(k)	Stock Options. Within one year of the Effective date, or upon an initial public offering of the capital stock of the Company, Company shall provide options in an amount to equal one-half of one percent of the
outstanding capital stock of the Company. 

  
 3 

	 	(l)	Relocation Expenses. The Company shall reimburse Executive of all reasonable expenses incurred in relocating his residence to Florida in a total amount not to exceed $40,000. Executive shall also receive
reimbursement for reasonable travel and temporary housing expenses in an amount to be agreed upon by the parties. 

  

	5.	Termination. 

  

	 	(a)	Death. This Agreement and Executive’s employment hereunder shall terminate immediately upon Executive’s death. 

  

	 	(b)	Disability. To the extent permitted by law, if Executive is (i) unable to engage in any substantial gainful activity by reason of any medically determinable physical or mental impairment that can be expected
to result in death or can be expected to last for a continuous period of not less than twelve (12) months, (ii) by reason of any medically determinable physical or mental impairment that can be expected to result in death or can be
expected to last for a continuous period of not less than twelve (12) months, receiving income replacement benefits for a period of not less than three months under the Company’s disability or health plan, or (iii) determined to be
totally disabled by the Social Security Administration, then upon at least 60 days’ prior written notice to Executive, if such is consistent with applicable law, Executive shall be considered disabled for purposes of this Agreement and the
Company may terminate this Agreement and Executive’s employment hereunder, unless, within that notice period, Executive shall have resumed performance of the essential functions of his positions, with or without reasonable accommodation.

  

	 	(c)	Termination by the Company. 

 (i) Termination for Cause. The
Company may terminate this Agreement and Executive’s employment hereunder at any time for Cause. As used herein, “Cause” shall mean: 
  

	 	(A)	a material breach by Executive of Executive’s duties and obligations hereunder, including but not limited to gross negligence in the performance of his duties and responsibilities, or the willful failure to follow
the Board’s directions, in each case, which has caused or is likely to cause material injury to the reputation or business of the Company; provided, however, that Cause shall not exist unless the Company has provided Executive with written
notice setting forth the existence of the non-performance, failure or breach and Executive shall not have cured same within thirty (30) days after receiving such notice; 

  
 4 

	 	(B)	willful misconduct by Executive that, in the reasonable determination of the Board, has caused or is likely to cause material injury to the reputation or business of the Company; 

 

	 	(C)	any criminal act of fraud, material misappropriation or other material dishonesty by Executive; or 

  

	 	(D)	Executive’s conviction of a felony, but specifically excluding any conviction based on vicarious liability (with “vicarious liability” meaning liability based on acts of the Company for which the
Executive is charged solely as a result of his service with the Company and in which he was not directly involved and did not have prior knowledge of such actions or intended actions). 

Executive shall be considered to have been discharged for Cause if the Company determines within 30 days after his resignation or discharge
that discharge for Cause was warranted. In the event of termination for Cause, the Company shall be obligated to pay Executive only Executive’s salary up to the date of termination and any earned but unpaid bonus with respect to any calendar
year ended prior to the date of termination. For purposes of this Agreement, no act or failure to act on the Executive’s part shall be considered “willful” unless it is done, or omitted to be done, by him in bad faith or without
reasonable belief that his action or omission was in the best interests of the Company or a Subsidiary. 
 Any act or failure to act based
upon authority given pursuant to a resolution duly adopted by the Board or based upon the advice of counsel for the Company or a Subsidiary shall be conclusively presumed to be done, or omitted to be done, in good faith and in the best interests of
the Company or a Subsidiary. 
 (ii) Termination Without Cause. Notwithstanding anything contained herein to the
contrary, the Company also may terminate this Agreement and Executive’s employment hereunder for reason other than death, Disability or Cause upon no less than 60 days’ prior written notice to Executive. The Company shall be deemed to have
terminated this Agreement without Cause in the event that this Agreement is terminated as a result of the Company’s giving notice of non-renewal prior to the end of the Initial Term or any Additional term as provided in Section 2 above.

  

	 	(d)	Termination by Executive Without Good Reason. Executive may terminate this Agreement and his employment hereunder for any reason whatsoever, upon no less than 60 days’ prior written notice to the Company.

  

	 	(e)	Termination by Executive For Good Reason. If Executive resigns for Good Reason, then Executive’s termination shall be treated as a termination by the Company without Cause pursuant to Section 5(c)(ii)
hereof. As used herein, a resignation for “Good Reason” shall mean a resignation by Executive within ninety (90) days following the initial existence of one or more of the following conditions arising without Executive’s consent:

  
 5 

 (i) A material reduction in Executive’s Annual Salary; 

(ii) A material diminution in Executive’s authority, duties, or responsibilities; 

(iii) A relocation of Executive’s principal place of employment by more than fifty (50) miles from its location at
the Effective Date of this Agreement; or 
 (iv) Any other action or inaction that constitutes a material breach by the
Company of this Agreement; 
 Provided, however, that Good Reason shall not exist unless Executive has provided the Company with a written
notice setting forth the reason(s) for the existence of Good Reason within ninety (90) days of the initial existence of the condition(s), and the Company has not cured the reason(s) for the existence of Good Reason within thirty (30) days
after receiving such notice. 
  

	 	(f)	Payments Upon Termination. 

 (i) Termination of Employment for any
Reason: The following payments will be made upon Executive’s termination of employment for any reason: 
  

	 	(A)	Earned but unpaid Annual Salary through the date of termination. 

  

	 	(B)	Bonus and all other forms of incentive compensation earned but unpaid at the time of termination for which the performance measurement period has ended and the performance goals attained (if applicable).

  

	 	(C)	Accrued but unpaid vacation. 

  

	 	(D)	Amounts payable under any of the Company’s employee benefit plans in accordance with the terms of those plans. 

  

	 	(E)	Unreimbursed expenses incurred by Executive on the Company’s behalf. 

 (ii)
Termination by Company without Cause or by Executive for Good Reason. In the event that the Company terminates this Agreement without Cause or the Executive terminates this Agreement for Good Reason, Executive shall be entitled to receive
(x) a lump sum severance payment equal to Executive’s Annual Salary at the time of termination (or, if greater, Annual Salary prior to the occurrence of Good Reason) plus Executives Average Annual Bonus, and (y) continuation of
Company-provided group health plan coverage, at the same level and cost applicable to Executive immediately prior to employment termination, until the second anniversary of the employment termination (the “Severance Benefits”). 

  
 6 

	 	(A)	If the Company is obligated by law (including the WARN Act or any similar state or foreign law) to pay Executive severance pay, a termination indemnity, notice pay, or the like, then the amount of such legally required
pay shall reduce the Severance Benefits hereunder. 

  

	 	(B)	For purposes of this Agreement, “Average Annual Bonus” means the average bonus for the three (3) fiscal years preceding the termination of employment. 

(iii) Termination Due to Disability. In the event that Executive employment terminates due to his Disability, the
Company shall continue paying Executive’s Base Salary until the third anniversary of such termination; provided that, the payments made by the Company under this paragraph shall be reduced, dollar-for-dollar, by the payment made to Executive
under any long-term disability plan, policy or program provided or contributed to by the Company. 
 (iv) Nonduplication
of Benefits. If Executive receives the Severance Benefits under this Section 5, he shall not be entitled to also receive the Change in Control Compensation under Section 6 hereof. 

 

	6.	Change in Control. 

  

	 	(a)	Change in Control Severance Compensation. If within twelve months following a Change in Control (as defined below) Executive’s employment with the Company is terminated by the Company without Cause or
Executive resigns for Good Reason, then Executive shall be entitled to receive from the Company a payment equal to 200% of the amount of the Severance Payment specified in Section 5(f)(ii) of this Agreement (or, if greater, Annual Salary prior
to the occurrence of Good Reason) plus Executives Average Annual Bonus, and (y) continuation of Company-provided group health plan coverage, at the same level and cost applicable to Executive immediately prior to employment termination, for
twenty-four (24) months following the employment termination (the “Change in Control Compensation”). Subject to Section 10 hereof, the cash portion of the Change in Control Compensation shall be payable in a single lump sum
payment within ten (10) days following the date of termination. The Executive shall be entitled to the Change in Control Compensation if, within six (6) months prior to the Change in Control, at the request or direction of a participant in
a potential acquisition, the Company terminates the Executive’s employment without Cause or causes a condition constituting Good Reason. 

  

	 	(b)	Change in Control. For purposes of this Agreement, “Change in Control” shall mean the occurrence of any of the following events: 

(i) The date any one person, or more than one “person” acting as a group, acquires (or has acquired during the
twelve-month period ending on the date of the most recent acquisition by such person(s)) ownership of common stock possessing 50% or more of the total voting power of the common stock of the Company; 

  
 7 

 (ii) Individuals who at any time during the term of this Agreement constitute the
board of directors of the Company (the “Incumbent Board”) cease for any reason to constitute at least a majority thereof, provided that any person becoming a director subsequent to the date hereof whose election or nomination for election
was approved by a vote of at least three-quarters of the directors comprising the Incumbent Board (either by a specific vote or by approval of the proxy statement of the Company in which such person is named as a nominee for director, without
objection to such nomination) shall be, for purposes of this clause (ii) considered as though such person were a member of the Incumbent Board; 

(iii) Any consolidation or merger to which the Company is a party, if following such consolidation or merger, stockholders of
the Company immediately prior to such consolidation or merger shall not beneficially own securities representing at least 51% of the combined voting power of the outstanding voting securities of the surviving or continuing corporation; or 

(iv) Any sale, lease, exchange or other transfer (in one transaction or in a series of related transactions) of all, or
substantially all, of the assets of the Company, other than to an entity (or entities) of which the Company or the stockholders of the Company immediately prior to such transaction beneficially own securities representing at least 51% of the
combined voting power of the outstanding voting securities. 
  

	 	(c)	Nonduplication of Benefits. If Executive receives any Change in Control Compensation under this Section 6, he shall not be entitled to receive any Severance Benefits under Section 5(c)(ii) or 5(e)
hereof. 

  

	 	(d)	General Release. Notwithstanding anything herein to the contrary, the payment of any Change in Control Compensation hereunder to Executive shall be subject to the execution by Executive (and failure to revoke) of
a general release and hold harmless of the Company and its affiliates of any and all claims under this Agreement or related to or arising out of Executive’s employment hereunder, in the form attached as hereto as Exhibit A.

  

	7.	Tax and Other Restrictions. Notwithstanding anything herein to the contrary: 

  

	 	(a)	Excess Parachute Payments. In the event that payment of any amount under this Agreement, including, but not limited to, any Severance Payment under Section 5(c)(ii) or 5(e) or Change in Control Compensation
under Section 6, would cause Executive to be the recipient of an excess parachute payment within the meaning of Code Section 280G(b), the amount of the payments to be made to Executive pursuant to this Agreement shall be reduced to an
amount equal to 299% of Executive’s “base amount” within the meaning of Code Section 280G. The manner in which such reduction occurs, including the items of payment and amounts thereof to be reduced, shall be determined by the
Company. 

  
 8 

	 	(b)	Payments in Excess of $1 Million. If any payment hereunder, including but not limited to, a Severance Payment under Section 5(c)(ii) or 5(e) or Change in Control Compensation under Section 6, would not
be deductible by the Company for federal income tax purposes by reason of Code Section 162(m), or any similar or successor statute (excluding Code Section 280G), such payment shall be deferred and the amount thereof shall be paid to
Executive at the earliest time that such payment shall be deductible by the Company. 

  

	8.	Covenants of the Executive and the Company. 

  

	 	(a)	Nonsolicitation. During the Employment Term and for a period of one year thereafter, Executive shall not, directly or indirectly, (i) employ, solicit for employment or otherwise contract for the services of
any individual who is or was an employee of the Company or any of its Subsidiaries during the Employment Term; (ii) otherwise induce or attempt to induce any employee of the Company or its Subsidiaries to leave the employ of the Company or such
Subsidiary, or in any way knowingly interfere with the relationship between the Company or any such Subsidiary and any employee respectively thereof, provided, however, that this clause (ii) shall not prohibit the activities described in the
preceding clause (i) following termination of the Employment Term with respect to any individual who was not an employee of the Company or its Subsidiaries during the Employment Term; or (iii) induce or attempt to induce any customer,
supplier, broker, agent, licensee or other business relation of the Company or any Subsidiary of the Company to cease doing business with the Company or such Subsidiary, or interfere in any way with the relationship between any such customer,
supplier, broker, agent, licensee or business relation and the Company or any subsidiary thereof. 

  

	 	(b)	 Nondisclosure. For the Employment Term and thereafter, (i) Executive shall not divulge, transmit or otherwise disclose (except as legally
compelled by court order, and then only to the extent required, after prompt notice to the Company’s Chief Executive Officer and Chief Legal Officer of any such order), directly or indirectly, other than in the regular and proper course of
business of the Company and its Subsidiaries, any confidential knowledge or information with respect to the operations or finances of the Company or any of its Subsidiaries or with respect to confidential or secret processes, methods, services,
techniques, reinsurance arrangements, customers or plans with respect to the Company or its Subsidiaries and (ii) Executive will not use, directly or indirectly, any confidential information for the benefit of anyone other than the Company and
its Subsidiaries; provided, however, that Executive has no obligation, express or implied, to refrain from using or disclosing to others any knowledge or information which is or hereafter shall become available to the general public other than
through disclosure by Executive, or as requested by regulatory bodies or as required by judicial courts. All new processes, techniques, know-how, methods, inventions, plans, products, patents and devices developed, made or invented by Executive,
alone or with others, while an employee of the Company which are related to the business of the Company and its Subsidiaries shall be and 

  
 9 

	 	
become the sole property of the Company, unless released in writing by the Board, and Executive hereby assigns any and all rights therein or thereto to the Company. 

 

	 	(c)	Nondisparagement. During the Employment Term and thereafter, Executive shall not take any action to disparage or criticize the Company or its Subsidiaries or their respective employees, directors, owners or
customers or to engage in any other action that injures or hinders the business relationships of the Company or its Subsidiaries. During the Employment Term and thereafter, the Company shall not take any action to disparage or criticize Executive to
any third parties. Nothing contained in this Section 8(c) shall preclude either Executive or the Company from (i) making truthful statements or disclosures that are required by applicable law, regulation or legal process or
(ii) enforcing their respective rights under this Agreement. 

  

	 	(d)	Noncompetition. In consideration of the payment to Executive of the Severance payments pursuant to Section 5(c)(ii) or 5(e) or Change in Control Compensation pursuant to Section 6, Executive hereby
agrees that, from and after the Termination Date, and for twelve (12) months thereafter, Executive shall not participate as a partner, joint venturer, proprietor, shareholder, employee or consultant, or have any other direct or indirect
financial interest (other than a less than 10% interest in a corporation whose shares are regularly traded on a national securities exchange or in the over-the-counter market), including, without limitation, the interest of a creditor in any form,
in, or in connection with, any business competing directly or indirectly with the business of the Company and its Subsidiaries in any geographic area where the Company and its Subsidiaries are actively engaged in conducting business as of the
Termination Date. The purpose of this restrictive covenant is to protect the Company’s trade secrets and other confidential information, including, without limitation, its business plans, processes and customer information. 

 

	 	(e)	Return of Company Property. All files, records, correspondence, memoranda, notes or other documents (including, without limitation, those in computer-readable form) or property relating or belonging to the
Company or its Subsidiaries or affiliates, whether prepared by Executive or otherwise coming into Executive’s possession in the course of the performance of his services under this Agreement, shall be the exclusive property of the Company and
shall be delivered to the Company, and not retained by Executive (including without limitations, any copies thereof), promptly upon request by the Company and, in any event, within 60 days following the Termination Date. 

 

	 	(f)	 Scope. The Company and Executive further acknowledge that the time, scope, geographic area and other provisions of this Section 8 have
been specifically negotiated by sophisticated commercial parties and agree that all such provisions are reasonable under the circumstances of the activities contemplated by this Agreement. In the event that the agreements in this Section 8
shall be determined by any court of competent jurisdiction to be unenforceable by reason of their 

  
 10 

	 	
extending for too great a period of time or over too great a geographical area or by reason of their being too extensive in any other respect, they shall be interpreted to extend only over the
maximum geographical area as to which they may be enforceable and/or to the maximum extent in all other respect as to which they may be enforceable, all as determined by such court in such action. 

 

	 	(g)	Enforcement. Both parties recognize that the services to be rendered under this Agreement by Executive are special, unique and of extraordinary character and that in the event of the breach by Executive or the
Company of any of the terms and conditions of this Section 8 to be performed by each party, then the Company or the Executive shall be entitled, if it so elects, to institute and prosecute proceedings in any court of competent jurisdiction,
either in law or in equity, to obtain damages for any breach hereof, or to enforce the specific performance hereof by Executive or the Company or to enjoin Executive or the Company from performing acts prohibited above during the period herein
covered, but nothing herein contained shall be construed to prevent such other remedy in the courts as the Company or the Executive may elect to invoke. 

  

	 	(h)	Other. If Executive competes with the Company or otherwise violates any of the restrictions contained in this Section 8, the Company shall have no obligation to pay the Severance Payment or Change of Control
Compensation or any remaining installment thereof to Executive. 

  

	9.	Indemnification and Insurance. The Company shall provide Executive (including Executive’s heirs, executors and administrators), at the Company’s expense, with coverage under a standard directors’
and officers’ (D&O) liability insurance policy, and shall indemnify Executive (and Executive’s heirs, executors and administrators) to the fullest extent permitted under Delaware law against all expenses and liabilities reasonably
incurred by Executive in connection with or arising out of any action, suit or proceeding in which Executive may be involved by reason of Executive’s having been a director or officer of the Company (whether or not Executive continues to be a
director or officer at the time of incurring such expenses or liabilities), such expenses and liabilities to include, but not be limited to, judgments, court costs and attorneys’ fees and the cost of reasonable settlements. The Company shall
cover the Executive under D&O liability insurance both during and, while potential liability exists, after the term of this Agreement in the same amount and to the same extent as the Company covers its other officers and directors. In the event
the referenced D&O liability policy is a “wasting” policy in that defense and litigation costs reduce the amount of insurance available for indemnification purposes, the Company agrees to provide Executive with full and complete
indemnification beyond the coverage limit offered by the D&O policy. 

  

	10.	Application of Code Section 409A. 

  

	 	(a)	 General. To the extent applicable, it is intended that this Agreement comply with the provisions of Code Section 409A, so as to prevent
inclusion in gross income of any amounts payable or benefits provided hereunder in a taxable year that is prior to the taxable year or years in which such amounts or benefits would 

  
 11 

	 	
otherwise actually be distributed, provided or otherwise made available to Executive. This Agreement shall be construed, administered, and governed in a manner consistent with this intent and the
following provisions of this Section shall control over any contrary provisions of this Agreement. 

  

	 	(b)	Restrictions on Specified Employees. In the event Executive is a “specified employee” within the meaning of Code Section 409A(a)(2)(B)(i) and delayed payment of any amount or commencement of any
benefit under this Agreement is required to avoid a prohibited distribution under Code Section 409A(a)(2), then amounts payable in connection with Executive’s termination of employment will be delayed and paid, with interest at the short
term applicable federal rate as in effect as of the termination date, in a single lump sum six months thereafter (or if earlier, the date of Executive’s death); provided, however, that payments to which Executive is entitled under Sections 5
and 6 of this Agreement need not be delayed under this Section 10(b) to the extent those payments would comply with the requirements of Treas. Reg. §1.409A-1(a)(b)(9), which generally requires that such payments not exceed two times the
lesser of (1) Executive’s annualized compensation based on his annual rate of pay in the year before the date of termination or (2) the Code Section 401(a)(17) limit applicable to qualified plans during the year of
Executive’s date of termination, or would otherwise be payable without delay without violating Section 409A. 

  

	 	(c)	Separation from Service. Payments and benefits hereunder upon Executive’s termination or severance of employment with the Company that constitute deferred compensation under Code Section 409A payable
shall be paid or provided only at the time of a termination of Executive’s employment which constitutes a “separation from service” within the meaning of Code Section 409A (subject to a possible six-month delay pursuant to the
subsection (b) above). 

  

	 	(d)	Separate Payments. For purposes of Code Section 409A, each payment under this Agreement shall be treated as a right to a separate payment for purposes of Code Section 409. 

 

	 	(e)	Reimbursements. All reimbursements and in kind benefits provided under this Agreement, including, but not limited to, payments under Sections 6, 7 and 9, shall be made or provided in accordance with the
requirements of Code Section 409A, including, where applicable, the requirement that (i) any reimbursement is for expenses incurred during Executive’s lifetime (or during a shorter period of time specified in this Agreement),
(ii) the amount of expenses eligible for reimbursement, or in kind benefits provided, during a calendar year may not affect the expenses eligible for reimbursement, or in kind benefits to be provided, in any other calendar year, (iii) the
reimbursement of an eligible expense will be made on or before the last day of the calendar year following the year in which the expense is incurred, and (iv) the right to reimbursement or in kind benefits is not subject to liquidation or
exchange for another benefit. 

  
 12 

	 	(f)	References to Code Section 409A. References in this Agreement to Code Section 409A include both that section of the Code itself and any guidance promulgated thereunder. 

 

	11.	Miscellaneous. 

  

	 	(a)	Modification. This Agreement may not be modified or amended except by an instrument in writing signed by the parties hereto. 

 

	 	(b)	Waiver. No term or condition of this Agreement shall be deemed to have been waived, nor shall there be any estoppel against the enforcement of any provision of this Agreement, except by written instrument of the
party charged with such waiver or estoppel. No such written waiver shall be deemed a continuing waiver unless specifically stated therein, and each such waiver shall operate only as to the specific term or condition waived and shall not constitute a
waiver of such term or condition for the future as to any act other than that specifically waived. 

  

	 	(c)	Notices. Any notice required or permitted to be given under this Agreement shall be sufficient if in writing and if sent by registered or certified mail to Executive or the Company at the address set forth below
or to such other address as they shall notify each other in writing: 

  

					
	If to the Company:	 		  	If to Executive:
			
	Old Guard Risk Services, Inc.	 		  	Christopher A. Pesch
	401 East Las Olas Boulevard, Suite 1650	 		  	To the last mailing address
	Fort Lauderdale, Florida 33301	 		  	on file with the Company.

  

	 	(d)	Assignment. This Agreement shall be binding upon and inure to the benefit of the Company and its successors and permitted assigns and Executive and personal representatives, heirs, legatees and beneficiaries.
This Agreement may be assigned by the Company with the consent of Executive to a fiscally responsible entity that assumes the obligations set forth herein, but shall not be assignable by Executive. 

 

	 	(e)	 Applicable Law. This Agreement shall be construed in accordance with the laws of the State of Florida in every respect, including, without
limitation, validity, interpretation and performance. Any dispute between the parties hereto, arising under or relating to this Agreement or Executive’s employment with the Company, other than for an action by the Company for specific
performance, injunction or other equitable remedy to enforce Section 8 hereof shall be settled by an arbitration administered by a single arbitrator in Fort Lauderdale, Florida. The arbitrator shall be selected upon mutual agreement of
Executive and Company. In the event the parties cannot agree on a single mediator, each party select one arbitrator and these two arbitrators will select the third arbitrator who will act as the final arbitrator in the arbitration proceedings.
Discovery, motion practice, and other administrative matters attendant to the litigation shall be 

  
 13 

	 	
conducted pursuant to the then prevailing discovery and motion rules in the US District Court for the Southern District at Florida and as interpreted by the relevant case law. The prevailing
party in any such arbitration may be awarded attorneys’ fees and expenses and judgment upon the award rendered may be entered in any court having jurisdiction thereof. 

 

	 	(f)	Headings. Section headings and numbers herein are included for convenience of reference only and this Agreement is not to be construed with reference thereto. If there be any conflict between such numbers and
headings and the text hereof, the text shall control. 

  

	 	(g)	Severability. If for any reason any portion of this Agreement shall be held invalid or unenforceable, it is agreed that the same shall not affect the validity or enforceability of the remainder hereof. The
portion of the Agreement which is not invalid or unenforceable shall be considered enforceable and binding on the parties and the invalid or unenforceable provision(s), clause(s) or sentence(s) shall be deemed excised, modified or restricted to the
extent necessary to render the same valid and enforceable and this Agreement shall be construed as if such invalid or unenforceable provision(s), clause(s), or sentences(s) were omitted. The provisions of this Section 11(g), as well as Sections
8 and 9 hereof, shall survive the termination of this Agreement. 

  

	 	(h)	Entire Agreement. This Agreement contains the entire agreement of the parties with respect to its subject matter and supersedes all previous agreements between the parties. No officer, employee, or representative
of the Company has any authority to make any representation or promise in connection with this Agreement or the subject matter thereof that is not contained therein, and Executive represents and warrants he has not executed this Agreement in
reliance upon any such representation or promise. No modification of this Agreement shall be valid unless made in writing and signed by the parties hereto. 

  

	 	(i)	Waiver of Breach. The waiver by either party of a breach of any provision of this Agreement by the other party shall not operate or be construed as a waiver of any subsequent breach by the breaching party.

  

	 	(j)	No Mitigation. In no event shall the Executive be obligated to seek other employment or take any other Action by way of mitigation of the amounts payable to the Executive under any of the provisions of this
Agreement, and such amounts shall not be reduced whether or not the Executive obtains other employment. 

  

	 	(k)	Counterparts. This Agreement may be executed in one or more counterparts, each of which shall be deemed to be an original, but all of which together shall constitute one agreement, 

  
 14 

 IN WITNESS WHEREOF, the Company has caused this Agreement to be executed by its duly
authorized officer and Executive has signed this Agreement all on the day and year first above written. 
  

							
	OLD GUARD RISK SERVICES, INC.	 		 	EXECUTIVE
		 	a Delaware corporation	 		 	
				
	By:	 	     /s/ Steven M. Mariano
	 		 	 /s/ Christopher A. Pesch

	Title:	 	President	 		 	Christopher A. Pesch

  
 15 

 Exhibit A to Executive Employment Agreement 

RELEASE AGREEMENT 

THIS RELEASE AGREEMENT is made and entered into this
                     day of                     
by and between Patriot National Insurance Group, Inc. and its subsidiaries (collectively the “Company”) and                     
(hereinafter “Executive”). 
 Executive’s employment with Company terminated on
                    ; and Executive has voluntarily agreed to the terms of this RELEASE AGREEMENT in exchange for severance benefits under the
Employment Agreement (“Employment Agreement”) to which Executive otherwise would not be entitled. 
 NOW THEREFORE, in
consideration for severance benefits provided under the Employment Agreement, Executive on behalf of himself and his spouse, heirs, executors, administrators, children, and assigns does hereby fully release and discharge Company, its officers,
directors, employees, agents, subsidiaries and divisions, benefit plans and their administrators, fiduciaries and insurers, successors, and assigns from any and all claims or demands for wages, back pay, front pay, attorney’s fees and other
sums of money, insurance, benefits, contracts, controversies, agreements, promises, damages, costs, actions or causes of action and liabilities of any kind or character whatsoever, whether known or unknown, from the beginning of time to the date of
these presents, relating to his employment or termination of employment from Company, including but not limited to any claims, actions or causes of action arising under the statutory, common law or other rules, orders or regulations of the United
States or any State or political subdivision thereof including the Age Discrimination in Employment Act and the Older Workers Benefit Protection Act. 

The Company presents that it is not presently aware of any cause of action that it or any of the other Company have against Executive as of
the date hereof. The Company acknowledges that this Release granted by Executive will be null and void in the event the Company subsequently brings a cause of action against Executive. 

Executive acknowledges that Executive’s obligations under Section 9 of the Employment Agreement shall continue to apply to
Executive. 
 This Release Agreement supersedes any and all other agreements between Executive and Company except agreements relating to
proprietary or confidential information belonging to Company and indemnification by the Company. This release does not affect Executive’s right to any benefits to which Executive may be entitled under any employee benefit plan, program or
arrangement sponsored or provided by Company, including but not limited to the Employment Agreement and the plans, programs and arrangements referred to therein. 

Executive and Company acknowledge that it is their mutual intent that the Age Discrimination in Employment Act waiver contained herein fully
comply with the Older Workers Benefit Protection Act. Accordingly, Executive acknowledges and agrees that: 
 (a) The
Severance benefits exceed the nature and scope of that to which he would otherwise have been legally entitled to receive; 

 (b) Execution of this Agreement and the Age Discrimination in Employment Act
waiver herein is his knowing and voluntary act; 
 (c) He has been advised by Company to consult with his personal attorney
regarding the terms of this Agreement, including the aforementioned waiver; 
 (d) He has had at least twenty-one
(21) calendar days within which to consider this Agreement; 
 (e) He has the right to revoke this Agreement in full
within seven (7) calendar days of execution and that none of the terms and provisions of this Agreement shall become effective or be enforceable until such revocation period has expired; 

(f) He has read and fully understands the terms of this Agreement; and 

(g) Nothing contained in this Agreement purports to release any of Executive’s rights or claims under the Age
Discrimination in Employment Act that may arise after the date of execution. 
 IN WITNESS WHEREOF, the parties have executed this Agreement
on the date indicated above. 
  

							
	OLD GUARD RISK SERVICES, INC.	 		 	EXECUTIVE
		 	a Delaware corporation	 		 	
				
	By:	 	  
	 		 	  

	Title:	 		 		 	Christopher A. Pesch

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00238-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00238-of-00352.parquet"}]]