Employment Agreement, Dirk Montgomery



 Exhibit 10.1 

EMPLOYMENT AGREEMENT 

THIS EMPLOYMENT AGREEMENT (this “Agreement”) is dated as of September 2, 2014 (the “Effective Date”),
by and between HEALTH INSURANCE INNOVATIONS, INC., a Delaware incorporated corporation (the “Company”), and DIRK A. MONTGOMERY (“Executive”). 

Recitals 
 A. The Company
desires to hire Executive, and Executive desires to be hired by the Company, upon the terms and conditions set forth herein; and 
 B. The
Company and Executive agree to protect the interests of the Company and Company’s customers and Confidential Information (as defined below) that may have been or that may be disclosed to Executive as set forth herein. 

Agreement 
 NOW,
THEREFORE, in consideration of the mutual promises made herein and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties, intending to be legally bound, agree as follows: 

Section 1. Employment, Duties and Acceptance. 

(a) The Company shall employ Executive during the Term (as defined below) as Executive Vice President and Chief Financial Officer. Executive
shall be responsible for performing the duties and exercising the powers which the Chief Executive Officer of the Company or the Board of Directors of the Company (the “Board”) may from time-to-time assign to him in his capacity as
Executive Vice President and Chief Financial Officer of the Company in connection with the conduct and management of the business of the Company and its subsidiaries and affiliates. 

(b) Executive hereby accepts such employment and agrees, during the Term, to render Executive’s services to the Company on a full-time
basis and to devote Executive’s full business time and attention to the business and affairs of the Company and any subsidiary or affiliate of the 

  
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Company. Executive agrees that at all times during the Term, Executive will faithfully perform the duties so assigned to him to the best of Executive’s ability. Executive further agrees to
accept election and to serve during all or any part of the Term as an officer, director or representative of any subsidiary or affiliate of the Company, without any compensation therefor other than that specified in this Agreement. Executive shall
report directly to the Company’s Chief Executive Officer. 
 (c) The duties to be performed by Executive hereunder shall be principally
performed at the Company’s offices located in Tampa, Florida, subject to reasonable travel requirements on behalf of the Company. Executive shall be entitled to an annual paid time off of 20 days on the same terms that the Company provides
to other similarly situated senior Company executives in accordance with the Company’s policies and practices; provided that Executive shall schedule the timing and duration of Executive’s vacations in a reasonable manner taking into
account the needs of the business of the Company. 
 (d) Executive acknowledges that from time to time the Company may promulgate workplace
policies and rules. Executive agrees to fully comply with all such policies and rules, and understands that failure to do so may result in a disciplinary action up to and including immediate discharge for Cause. 

Section 2. Term. As used herein, the “Term” means the period commencing on the Effective Date and
ending on September 2, 2015. The Term shall be automatically extended for successive one-year periods unless Executive or the Company gives written notice of termination on or before the 30th day prior to the expiration of any Term of its
desire not to renew the Term. Any such renewal shall be upon the terms and conditions set forth herein unless otherwise agreed between the Company and Executive. In the event that the Company gives written notice that it does not intend to renew the
Term, Executive shall be entitled to the benefits set forth in Section 4(b)(iii). 
 Section 3.
Compensation. Executive shall be entitled to the following compensation: 
 (a) The Company agrees to pay to Executive a
salary in cash (the “Salary”), as 

  
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compensation for the services to be performed by Executive, at the rate of $425,000 per calendar year, paid in accordance with the Company’s customary payroll procedures and subject to
applicable withholding. Based on Executive’s performance, Executive will receive a merit increase for calendar year 2015, effective January 1, 2015, in an amount to be determined by the Board in its sole discretion. During the Term, the
Board shall have the right to increase, but not decrease, the Salary, except the Board may decrease the Salary in connection with a base salary decrease that is generally applicable to all members of the Company’s senior management. Without
limiting the generality of the foregoing, Executive will be eligible for additional annual salary merit increases during the Term beginning in 2016 based on the evaluation of Executive’s performance as determined by the Board in its sole
discretion. Executive’s salary as in effect from time to time shall constitute the “Salary” for purposes of this Agreement. 

(b) On the Effective Date, the Company shall execute and deliver to the Executive (i) a Restricted Stock Award Agreement in the form
attached hereto as Exhibit B (the “RSA Agreement”), evidencing a grant to Executive pursuant to the terms of the Health Insurance Innovations, Inc. Long Term Incentive Plan (the “LTI Plan”) of 150,000
shares of Restricted Stock (as defined in the RSA Agreement) and (ii) a Stock Appreciation Rights Award Agreement in the form attached hereto as Exhibit C (the “SARA Agreement”), evidencing a grant to Executive
pursuant to the terms of the LTI Plan) of 175,000 SARs (as defined in the SARA Agreement). During the Term, additional merit grants under the LTI Plan may be made to Executive based on the evaluation of Executive’s performance as determined by
the Board in its sole discretion.
 (c) Executive shall be paid a signing bonus in the amount of $50,000, subject to applicable withholding,
on the date of Executive’s first regular paycheck following the Effective Date. 
 (d) The Company shall reimburse Executive for all
reasonable expenses incurred by Executive in the course of performing Executive’s duties under this Agreement that are consistent with the Company’s policies in effect from time to time with respect to travel, entertainment and other
business expenses, subject to the Company’s requirements with respect to reporting and documentation of such expenses. 

  
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 (e) Executive shall be eligible to participate in any equity incentive plan, restricted share
plan, share award plan, stock appreciation rights plan, stock option plan or similar plan adopted by the Company on the same terms and conditions applicable to other senior Company executives, with the amount of such awards to be determined by the
Board in its sole discretion. Executive shall be eligible for an annual bonus and long term incentive awards as determined at the sole discretion of the Board. Executive’s target bonus will be equal to 50% of Executive’s Salary then in
effect; provided, that Executive will be considered for a pro-rated bonus for calendar year 2014, and Executive will be paid a minimum bonus of $112,500 for calendar year 2015 if Executive continues to be employed by the Company at the time such
bonus is payable. 
 (f) Executive shall be entitled to all rights and benefits for which Executive shall be eligible under any retirement,
retirement savings, profit-sharing, pension or welfare benefit plan, life, disability, health, dental, hospitalization and other forms of insurance and all other so-called “fringe” benefits or perquisites (except for with respect to any
plan that provides severance or other similar benefits), on the same terms that the Company provides to other similarly situated senior Company executives (subject to all restrictions on participation that may apply under federal and state tax
laws). 
 Section 4. Termination. 

(a) Events of Termination. Executive’s employment with the Company shall terminate (the date of such termination being the
“Termination Date”) immediately upon any of the following: 
 (i) Executive’s death (“Termination Upon
Death”); 
 (ii) the effective date of a written notice sent to Executive stating the Company’s determination, made in good
faith, that due to a mental or physical condition, Executive has been unable and failed to substantially render the services to be provided by Executive to the Company for a period of at least 180 days out of any consecutive 360 days
(“Termination For Disability”); 

  
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 (iii) the effective date of a written notice sent to Executive stating the Company’s
determination, made in good faith, that it is terminating Executive’s employment for Cause (as defined below) (“Termination For Cause”); 

(iv) the effective date of a notice sent to Executive stating that the Company is terminating Executive’s employment without Cause
(including any notice from the Company to Executive pursuant to Section 2 that the Company has decided not to renew the Term), which notice can be given by the Company at any time after the Effective Date at the Company’s sole
discretion, for any reason or for no reason (“Termination Without Cause”); 
 (v) the effective date of a notice (other
than a notice delivered pursuant to Section 4(a)(vi) of this Agreement) sent to the Company from Executive stating that Executive is electing to terminate Executive’s employment with the Company without Good Reason
(“Resignation Without Good Reason”); or 
 (vi) the effective date of a written notice to Company stating Executive’s
determination, made in good faith, that a Good Reason Event (as defined below) has occurred within 30 days preceding such notice and as a consequence Executive is electing to terminate Executive’s employment hereunder for a Good Reason
Event (“Resignation For Good Reason”); provided, however, that Executive will give the Company 30 days to cure such Good Reason Event, and if the Company fails to cure such Good Reason Event within 30 days after
Executive gives written notice of resignation hereunder, then Executive may immediately terminate Executive’s employment with the Company, and such termination will be a Resignation For Good Reason hereunder; provided, further, that
Executive’s termination shall be deemed a Termination For Cause if the Company has delivered to Executive written notice of any act or omission that, if not cured, would constitute Cause at any time preceding the notice provided by Executive
hereunder. 
 As used herein, the term “Cause” shall mean (i) commission of a willful act of dishonesty in the course
of Executive’s duties hereunder, (ii) conviction by a court of competent jurisdiction of, or plea of no contest to, a crime constituting a felony or conviction in respect of, or plea of no contest to, any act involving fraud, dishonesty or
moral turpitude, (iii) Executive’s performance under the influence of controlled substances (other than those taken pursuant to a medical doctor’s orders), or 

  
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continued habitual intoxication, during working hours, (iv) frequent or extended, and unjustifiable, absenteeism, (v) Executive’s personal misconduct or refusal to perform duties
and responsibilities or to carry out the lawful directives of the Chief Executive Officer of the Company or the Board, which, if capable of being cured shall not have been cured, within 30 days after the Company shall have advised Executive in
writing of its intention to terminate Executive’s employment, or (vi) Executive’s material non-compliance with the terms of this Agreement, which, if capable of being cured, shall not have been cured within 30 days after the Company
shall have advised Executive in writing of its intention to terminate Executive’s employment for such reason. 
 As used herein, the
term “Good Reason Event” shall mean (i) a material adverse change in the responsibilities or duties of Executive as set forth in this Agreement (including a change in reporting where Executive no longer reports directly to the
Chief Executive Officer of the Company, or a change in Executive’s capacity as Executive Vice President and Chief Financial Officer) without Executive’s prior consent at a time when there are no circumstances pending that would permit the
Board to terminate Executive for Cause, such that Executive is no longer acting as part of the senior management team of the Company, (ii) any reduction in the Salary or a material reduction in Executive’s benefits (other than (x) a
reduction in Salary that is the result of an administrative or clerical error, and which is cured within 15 business days after the Company receives notice of such failure or (y) a reduction in Salary or benefits that are generally
applicable to all members of the Company’s senior management), (iii) a material breach by the Company of this Agreement that is not cured within 30 days following the Company’s receipt of written notice of such breach from
Executive, or (iv) without Executive’s prior written consent, the relocation of Executive’s principal place of employment outside of a 30 mile radius from the location of the Company’s offices in Tampa, Florida as of the
Effective Date. With regard to clause (i), Executive acknowledges that the Company has flexibility under Section 1(a) to assign Executive a broad range of responsibilities and duties that are consistent with him being a member of the
senior management team and such assignments will not constitute a “Good Reason Event.” 

  
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 (b) Effect of Termination. 

(i) Death or Disability. In the event of Termination Upon Death or Termination For Disability pursuant to Sections 4(a)(i)
or 4(a)(ii) of this Agreement: 
 (A) Executive (or Executive’s legal representative) shall be entitled to
receive in cash an amount equal to any earned but unpaid Salary owing by the Company to Executive as of the Termination Date (the “Accrued Salary”); 

(B) Executive (or Executive’s legal representative) shall be entitled to receive in cash, to the extent provided under
any management bonus plan, an amount equal to the pro rata portion, determined as of the Termination Date, of any bonus to which Executive would have been entitled had Executive been employed by the Company at the time such bonus would have
otherwise been paid (the “Accrued Bonus”); 
 (C) all unvested Restricted Shares subject to the RSA
Agreement shall become fully vested and non-forfeitable as of the Termination Date; and 
 (D) unvested SARs subject to the
SARA Agreement shall become fully vested and non-forfeitable as of the Termination Date, and all SARS subject to the SARA Agreement shall remain exercisable until 5:00 p.m., Eastern time, on the date that is one year after the Termination Date. 

(ii) Termination For Cause. In the event of a Termination For Cause pursuant to Section 4(a)(iii) of this Agreement,
Executive shall be entitled to receive in cash an amount equal to any Accrued Salary. 
 (iii) Termination Without Cause and Resignation
For Good Reason and Termination Upon Non-renewal. In the event of Termination Without Cause or Resignation For Good Reason pursuant to Sections 4(a)(iv) or 4(a)(vi) of this Agreement, subject to Section 4(c)(ii) of
this Agreement: 
 (A) a Executive (or Executive’s legal representative) shall be entitled to receive in cash an amount
equal to the Accrued Salary; 

  
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 (B) Executive (or Executive’s legal representative) shall be entitled to
receive in cash an amount equal to the Accrued Bonus; 
 (C) Executive (or Executive’s legal representative) shall be
entitled to receive in cash an amount equal to, as applicable: (1) if the Termination Date is on or prior to the second anniversary of the Effective Date, two times Executive’s Salary (at the rate then in effect, and without taking into
account any reductions that would have given rise to Good Reason termination by Executive), payable in equal installments in accordance with the Company’s customary payroll procedures commencing on the Termination Date and ending 24 months
thereafter or (2) if the Termination Date is after the second anniversary of the Effective Date, Executive’s Salary (at the rate then in effect, and without taking into account any reductions that would have given rise to Good Reason
termination by Executive), payable in equal installments in accordance with the Company’s customary payroll procedures commencing on the Termination Date and ending 12 months thereafter; 

(D) all unvested Restricted Shares subject to the RSA Agreement shall become fully vested and non-forfeitable as of the
Termination Date; and 
 (E) unvested SARs subject to the SARA Agreement shall become fully vested and non-forfeitable as of
the Termination Date, and all SARS subject to the SARA Agreement shall remain exercisable until 5:00 p.m., Eastern time, on the date that is one year after the Termination Date. 

(iv) Resignation Without Good Reason. In the event of Resignation Without Good Reason pursuant to Section 4(a)(v) of this
Agreement, Executive shall be entitled to receive in cash an amount equal to any Accrued Salary. 
 (v) Upon Termination For Any
Reason. In the event of any termination, Executive shall be entitled to receive: 
 (A) any unpaid reasonable,
reimbursable business expenses incurred by Executive in the course of performing Executive’s duties under this Agreement that were incurred in a manner consistent with the Company’s policies in effect from time to time with respect to
travel, entertainment and other business expenses, subject to the Company’s requirements with respect to incurring, reporting and documenting such expenses; and 

(B) benefits under the Company’s benefit plans of general application as shall be determined under the provisions of
those plans. 

  
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 (c) Additional Provisions. 

(i) Any amounts to be paid pursuant to this Section 4 shall be paid in accordance with the Company’s existing payroll or
bonus payment practices, as applicable. 
 (ii) As a condition to the Company’s obligations, if any, to make any Accrued Bonus and
severance payments provided under Section 4(b)(iii)(B) and (C), Executive shall have executed, delivered and not revoked a general release in the form attached hereto as Exhibit A. 

(iii) Notwithstanding any provision of this Agreement, the obligations and commitments under Section 5 of this Agreement shall
survive and continue in full force and effect in accordance with their terms notwithstanding any termination of Executive’s employment for any reason or termination of this Agreement for any reason. 

(iv) Notwithstanding anything in this Agreement to the contrary, the Company shall have no obligation to pay any amounts payable under
Sections 4(b)(i)(B), 4(b)(iii)(B) or 4(b)(iii)(C) of this Agreement during such times as Executive is in breach of Section 5 of this Agreement, after the Company provides Executive with notice of such breach.

 (v) Executive agrees that termination of Executive’s employment for any reason shall, with no further action by Executive required,
constitute Executive’s resignation, as of the Termination Date and to the extent applicable, from all positions as an officer, director or representative of the Company and any subsidiary or affiliate of the Company. 

  
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 Section 5. Noncompetition, Nonsolicitation And Confidentiality.

 (a) Definitions. 

“Company’s Business” means (i) developing and administering web-based individual and/or group health insurance
plans and ancillary insurance products, (ii) designing and structuring data-driven individual and/or group health insurance plans and ancillary insurance products, (iii) marketing such individual and/or group health insurance plans and
ancillary insurance products, (iv) managing relations with insureds, (v) the development and maintenance of insurance and call center-oriented software and information technology systems, (vi) the development and maintenance of
information technology systems to facilitate the comparison of health insurance plans and (vii) any other business or commercial activity, in each case as conducted by the Company or any parent, subsidiary or other affiliate of the Company.

 “Competitor” means any company, other entity or association or individual that directly or indirectly is engaged in the
Company’s Business. 
 “Confidential Information” means any confidential information with respect to the
Company’s Business and/or the businesses of its clients or customers, including, but not limited to: the trade secrets of the Company; products or services; standard proposals; standard submissions, surveys and analyses; Commercial Lines
Quality Assurance Manual; Claims Services Department Procedures and Quality Assurance Manual; Surety Quality Assurance Manual; policy forms; fees, costs and pricing structures; marketing information; advertising and pricing strategies; analyses;
reports; computer software, including operating systems, applications and program listings; flow charts; manuals and documentation; data bases; all copyrightable works; the Company’s existing and prospective clients and customers, their
addresses or other contact information and/or their confidential information; existing and prospective client and customer lists and other related data; expiration periods; policy numbers; coverage specifications; daily reports and related
correspondence; premium renewal notices; and all similar and related information in whatever form. The term Confidential Information does not include, and there shall be no obligation hereunder with respect to, information that (i) is generally
available to the public on the date of this Agreement, (ii) becomes generally available to the public other than as a result of a disclosure by Executive not otherwise permissible hereunder or (iii) Executive has learned or learns from
other sources where, to Executive’s knowledge, such sources have not violated their confidentiality obligation to the Company or any other applicable obligation of confidentiality. 

  
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 (b) Noncompetition. Executive covenants and agrees that during the period commencing on
the Effective Date and ending two years following the Termination Date (the “Restricted Period”), Executive will not, directly or indirectly, own, manage, operate, control, render service to, or participate in the ownership,
management, operation or control of any Competitor anywhere in the United States of America; provided, however, that Executive shall be entitled to own shares of stock of any corporation having a class of equity securities actively traded on a
national securities exchange or on the Nasdaq Stock Market which represent, in the aggregate, not more than 1% of such corporation’s fully-diluted shares. 

(c) Nonsolicitation of Employees. Executive covenants and agrees that during the Restricted Period, Executive will not, directly or
indirectly, employ or solicit, or receive or accept the performance of services by any then current officer, manager, employee or independent contractor of the Company or any subsidiary or affiliate of the Company, or in any way interfere with the
relationship between the Company or any subsidiary or affiliate of the Company, on the one hand, and any such officer, manager, employee or independent contractor, on the other hand. 

(d) Nonsolicitation of Customers and Vendors. Executive covenants and agrees that during the Restricted Period, Executive will not,
directly or indirectly, knowingly induce, or attempt to induce, any customer, salesperson, distributor, supplier, vendor, manufacturer, representative, agent, jobber, licensee or other person known by Executive to be transacting business with the
Company or any subsidiary or affiliate of the Company (collectively the “Customers” and “Vendors”) to reduce or cease doing business with the Company or any such subsidiary or affiliate of the Company, or in any way
to interfere with the relationship between any such Customer or Vendor, on the one hand, and the Company or any subsidiary or affiliate of the Company, on the other hand. 

(e) Representations and Covenants by Executive. Executive represents and warrants that: (i) Executive’s execution, delivery
and performance of this Agreement do not and will not conflict with, breach, violate or cause a default under any contract, agreement, instrument, order, judgment or decree to which Executive is a party or by which Executive is bound;
(ii) Executive is not a party to or bound by any employment agreement, noncompete agreement or confidentiality 

  
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agreement with any other person or entity (other than the Company) and Executive is not subject to any other agreement that would prevent Executive from performing Executive’s duties for the
Company or otherwise complying with this Agreement; (iii) Executive is not subject to or in breach of any nondisclosure agreement, including any agreement concerning trade secrets or confidential information owned by any other party; and
(iv) upon the execution and delivery of this Agreement by the Company, this Agreement shall be the valid and binding obligation of Executive, enforceable in accordance with its terms. 

(f) Nondisclosure of Confidential Information. Executive hereby acknowledges and represents that Executive has consulted with
independent legal counsel regarding Executive’s rights and obligations under this Agreement and that Executive fully understands the terms and conditions contained herein and Executive agrees that Executive will not, directly or indirectly:
(i) use, disclose, reverse engineer or otherwise exploit for Executive’s own benefit or for the benefit of anyone other than the Company the Confidential Information except as authorized by the Company; (ii) during Executive’s
employment with the Company, use, disclose, or reverse engineer (x) any confidential information or trade secrets of any former employer or third party, or (y) any works of authorship developed in whole or in part by Executive during any
former employment or for any other party, unless authorized in writing by the former employer or third party; or (iii) upon Executive’s resignation or termination (x) retain Confidential Information, including any copies existing in
any form (including electronic form), that are in Executive’s possession or control, or (y) destroy, delete or alter the Confidential Information without the Company’s consent. Notwithstanding the foregoing, Executive may use the
Confidential Information in the course of performing Executive’s duties on behalf of the Company or any subsidiary or affiliate of the Company as described hereunder, provided that such use is made in good faith. Executive will immediately
surrender possession of all Confidential Information to Company upon any suspension or termination of Executive’s employment with Company for any reason. 

(g) Inventions and Patents. Executive acknowledges that all (i) inventions, innovations, improvements, developments, methods,
designs, analysis, drawings, reports, processes, novel concepts and all similar or related information (whether or not patentable) that relate to the Company’s or any of its subsidiaries’ or affiliates’ actual or anticipated
businesses, (ii) research and 

  
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development and (iii) existing or future products or services that are, to any extent, conceived, developed or made by Executive while employed by the Company or any subsidiary or affiliate
of the Company (“Work Product”) belong to the Company or such subsidiary or affiliate. Executive shall promptly disclose such Work Product to the Board and, at the cost and expense of the Company, perform all actions reasonably
necessary or requested by the Board (whether during or after the Term) to establish and confirm such ownership (including, without limitation, executing assignments, consents, powers of attorney and other instruments). 

(h) Miscellaneous. 
 (i)
Executive acknowledges that (x) Executive’s position is a position of trust and responsibility with access to Confidential Information of the Company, (y) the Confidential Information, and the relationship between the Company and each
of its employees, Customers and Vendors, are valuable assets of the Company and may not be converted to Executives own use and (z) the restrictions contained in this Section 5 are reasonable and necessary to protect the legitimate
business interests of the Company and will not impair or infringe upon Executive’s right to work or earn a living after Executive’s employment with the Company ends. 

(ii) Each of the foregoing obligations shall be enforceable independent of any other obligation, and the existence of any claim or cause of
action that Executive may have against the Company, whether predicated on this Agreement or otherwise, shall not constitute a defense to the enforcement by the Company of these obligations. 

(iii) Executive acknowledges that monetary damages will not be an adequate remedy for the Company in the event of a breach of this Agreement
and that it would be impossible for the Company to measure damages in the event of such a breach. Therefore, Executive agrees that, in addition to other rights that the Company may have at law or equity, the Company is entitled, without posting
bond, to seek an injunction preventing Executive from any breach of this Agreement. 
 (iv) In the event of a breach or violation by
Executive during the Restricted Period of any restriction in Section 5(b), (b) or (d) of this Agreement, the Restricted Period shall be tolled until such breach or violation has been cured. 

  
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 (v) The parties intend to provide the Company with the maximum protection possible with respect
to its Customers and Vendors. The parties, however, do not intend to include a provision that contravenes the public policy of any state. Therefore, if any provision of this Section 5 is unlawful, against public policy or otherwise
declared void, such provision shall not be deemed part of this Agreement, which otherwise shall remain in full force and effect. If, at the time of enforcement of this Agreement, a court or other tribunal holds that the duration, scope or area
restriction stated herein is unreasonable under the circumstances then existing, the parties agree that the court should enforce the restrictions to the extent it deems reasonable. 

(vi) Executive hereby agrees that prior to accepting employment with any other person or entity during the Term or during the Restricted
Period following the Termination Date, Executive will provide such prospective employer with written notice of the existence of this Agreement and the provisions of this Section 5 of this Agreement, with a copy of such notice delivered
simultaneously to the Company in accordance with Section 10 of this Agreement. 
 (vii) Notwithstanding any provision of this
Agreement, the obligations and commitments of this Section 5 shall survive and continue in full force and effect in accordance with their terms notwithstanding any termination of Executive’s employment for any reason or termination
of this Agreement for any reason. 
 Section 6. Withholding Taxes. Prior to making any payments required to be
made pursuant to this Agreement, the Company may require that the Company be reimbursed in cash for any taxes required by any government to be withheld or otherwise deducted and paid by the Company in respect of such payment by the Company. In lieu
thereof, the Company shall have the right to withhold the amount of such taxes from any sums due or to become due from it to Executive. 

Section 7. Expenses. In the event of any legal action to enforce Executive’s or the Company’s rights under
this Agreement, each party will be responsible for that party’s reasonable attorneys’ fees, expenses and disbursements. 

  
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 Section 8. Assignment. This Agreement is binding upon and shall
inure to the benefit of the parties hereto and their respective successors and assigns. Executive shall not assign or transfer any rights or obligations hereunder. The Company shall have the right to assign or transfer any rights or obligations
hereunder only to (a) a successor entity in the event of a merger, consolidation, or transfer or sale of all or substantially all the assets of the Company or (b) a subsidiary or affiliate of the Company. Any purported assignment, other
than as provided above, shall be null and void.  
 Section 9. Indemnification. The Company shall indemnify
Executive for any act or omission done or not done in performance of Executive’s duties hereunder in accordance with the Company’s certificate of incorporation, by-laws and any other constituent document to the extent provided for any
other officer or member of the Board. The Company’s obligations under this Section 9 shall survive any termination of this Agreement or Executive’s employment hereunder. In addition, on the Effective Date, the Company shall
execute and deliver to Executive an Indemnification Agreement in the form attached hereto as Exhibit D. 
 Section 10.
Notices. All notices, requests, consents and other communications required or permitted to be given hereunder, shall be in writing and shall be delivered personally or sent by prepaid telegram, telex, facsimile transmission,
overnight courier or mailed, first class, postage prepaid by registered or certified mail, as follows:  
  

			
	If to the Company:	  	Health Insurance Innovations, Inc.
		  	15438 N. Florida Avenue, Suite 201
		  	Tampa, Florida 33613
		  	Attention: Chief Executive Officer
		  	Telecopy: (877) 376-5832
		
		  	with a copy to (which shall not constitute notice hereunder):
		
		  	Health Insurance Innovations, Inc.
		  	15438 N. Florida Avenue, Suite 201
		  	Tampa, Florida 33613
		  	Attention: General Counsel
		  	Telecopy: (877) 376-5832
		
	If to Executive:	  	To Executive’s address as reflected on the payroll records of the Company



  
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 or such other address as either party shall designate by notice in writing to the other in accordance herewith.
Any such notice shall be deemed given when so delivered personally, by telex, facsimile transmission or telegram, or if sent by overnight courier, one day after delivery to such courier by the sender or if mailed, five days after deposit by the
sender in the U.S. mails. 
 Section 11. Entire Agreement. This Agreement shall constitute the entire agreement
between Executive and the Company concerning the subject matter hereof. This Agreement supersedes and preempts any prior employment agreement or other understandings, agreements or representations by or among the parties, written or oral, that may
have related to the subject matter hereof. No provisions of this Agreement may be modified, waived or discharged unless such waiver, modification or discharge is agreed to in writing, signed by Executive and an authorized officer of the Company.

 Section 12. Governing Law. This Agreement shall be subject to and governed by the laws of the State of Florida,
without giving effect to the principles of conflicts of law under Florida law that would require or permit the application of the laws of a jurisdiction other than the State of Florida and irrespective of the fact that the parties now or at any time
may be residents of or engage in activities in a different state. Employee agrees that in the event of any dispute or claim arising under this Agreement, jurisdiction and venue shall be vested and proper, and Employee hereby consents to the
jurisdiction of any court sitting in Tampa, Florida, including the United States District Court for the Middle District of Florida. 

Section 13. Full Settlement. Executive acknowledges and agrees that, subject to the payment by the Company of the
benefits provided in this Agreement to Executive, in no event will the Company nor any subsidiary or affiliate thereof be liable to Executive for damages under any claim of breach of contract as a result of the termination of Executive’s
employment. In the event of any such termination, the Company shall be liable only to provide to Executive, or Executive’s heirs or beneficiaries, the benefits specified in this Agreement. 

  
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 Section 14. Strict Compliance. Executive’s or the Company’s
failure to insist upon strict compliance with any provision of this Agreement or the failure to assert any right Executive or the Company may have hereunder shall not be deemed to be a waiver of such provision or right or any other provision or
right of this Agreement. The waiver, whether express or implied, by either party of a violation of any of the provisions of this Agreement shall not operate or be construed as a waiver of any subsequent violation of any such provision. 

Section 15. Creditor Status. No benefit or promise hereunder shall be secured by any specific assets of the Company.
Executive shall have only the rights of an unsecured general creditor of the Company in seeking satisfaction of such benefits or promises. 

Section 16. Section 409A. This Agreement is intended to comply with the requirements of Section 409A of
the Internal Revenue Code of 1986, as amended (“Section 409A”), and shall be construed accordingly. Any payments or distributions to be made to Executive under this Agreement upon a separation from service of amounts classified
as “nonqualified deferred compensation” for purposes of Section 409A, shall in no event be made or commence until six months after such separation from service if Executive is determined to be a specified Executive of a public
company (all as determined under Section 409A). Each payment of nonqualified deferred compensation under this Agreement shall be treated as a separate payment for purposes of Section 409A. Any reimbursements made pursuant to this Agreement
shall be paid as soon as practicable but no later than 90 days after Executive submits evidence of such expenses to the Company (which payment date shall in no event be later than the last day of the calendar incurred). The amount of such
reimbursements paid and any in-kind benefits the year following the calendar year in which the expense was provided during any calendar year shall not affect the reimbursements paid or in-kind benefits provided in any other calendar year, and the
right to any such payments and benefits shall not be subject to liquidation or exchange for another payment or benefit. 

Section 17. Cooperation. Executive agrees to provide assistance to and cooperate with the Company upon its
reasonable request with respect to matters within the scope of Executive’s duties and responsibilities during the Restricted Period. During such Period, the Company shall, to the 

  
 17 








 
maximum extent coordinate or cause any such request with Executive’s other commitments and responsibilities to minimize the degree to which such request interferes with such commitments and
responsibilities. The Company agrees that it will reimburse Executive for reasonable documented travel expenses (i.e., travel, meals and lodging) that Executive may incur in providing assistance to the Company hereunder. 

Section 18. Non-disparagement. Executive agrees to not make any statements, written or oral, while
employed by the Company and thereafter, which would be reasonably likely to disparage or damage the Company, its affiliates or subsidiaries or the personal or professional reputation of any present or former employees, officers or members of the
managing or directorial boards or committees of the Company or its affiliates or subsidiaries. The Company agrees that it will instruct each of its and its affiliates’ and subsidiaries’ members, directors, managers, officers and employees
not to make any disparaging communication regarding Executive, and no such person or entity will be authorized on the Company’s or any affiliate’s or subsidiary’s behalf to make any such disparaging communications regarding Executive.
 
 Section 19. Recoupment. Executive agrees to reimburse the Company for all or a portion, as
determined below, of any bonus or incentive or equity-based compensation paid or awarded to Executive by the Company, if the Board determines that (a) the payment, award or vesting thereof was predicated upon the achievement of certain
financial results that were subsequently the subject of a material financial restatement, (b) Executive engaged in fraud or misconduct that caused, in whole or in part, the need for the material financial restatement, and (c) a lower
payment, award or vesting would have occurred based upon the restated financial results. In such event, Executive agrees to reimburse (in the manner determined by the Board, including cancellation of options or other stock awards) any bonus or
incentive or equity-based compensation previously paid, awarded or vested in the amount by which such bonus or incentive or equity-based compensation actually paid, awarded or vested exceeds the lower payment, award or vesting that would have
occurred based upon the restated financial result; provided that no reimbursement shall be required if the payment, award or vesting otherwise subject to reimbursement hereunder occurred more than three (3) years prior to the date the
applicable reinstatement is disclosed. In addition, notwithstanding anything to the contrary, any bonus or incentive or equity-based compensation, or other 

  
 18 








 
compensation, payable to Executive pursuant to this Agreement or any other agreement, plan or arrangement of the Company shall be subject to repayment or recoupment (clawback) by the Company to
the extent applicable under Section 304 of the Sarbanes-Oxley Act of 2002 (and not otherwise exempted) and in accordance with such policies and procedures as the Board or the Compensation Committee of the Board may adopt from time to time,
including policies and procedures to implement applicable law (including, but not limited to, Section 954 of the Dodd-Frank Act), stock market or exchange rules and regulations or accounting or tax rules and regulations. 

Section 20. Survival. Any provision of this Agreement that is expressly or by implication intended to survive
the termination of this Agreement shall survive or remain in effect after the termination of this Agreement.  
 Section 21.
Counterparts. This Agreement may be executed in two or more counterparts, anyone of which need not contain the signature of more than one party, but all such counterparts taken together shall constitute one and the same
agreement.  
 [Signature Page Follows] 

  
 19 








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

			
	HEALTH INSURANCE INNOVATIONS, INC.
		
	By:	 	 /s/ Michael W. Kosloske

		 	Michael W. Kosloske
		 	Chairman, President and Chief Executive Officer
	
	EXECUTIVE
	
	 /s/ Dirk A. Montgomery

	Dirk A. Montgomery



  
 20 








 EXHIBIT A 

FORM OF RELEASE 

This RELEASE (“Release”) is granted effective as of the
[—] day of [—], 20[—] by DIRK
A. MONTGOMERY (the “Executive”) in favor of HEALTH INSURANCE INNOVATIONS, INC. (the “Company”) and the other Released Parties (as defined below). This is the Release referred to in the Employment Agreement, dated as
of September 2, 2014, between the Company and the Executive (the “Employment Agreement”). The Executive gives this Release in consideration of the Company’s promises and covenants contained in the Employment Agreement,
with respect to which this Release is an integral part.  
 1. Release of the Company. The Executive, for himself, his
successors, assigns, attorneys, and all those entitled to assert his rights, now and forever hereby releases and discharges the Company and its respective officers, directors, stockholders, trustees, Executives, agents, parent corporations,
subsidiaries, affiliates, estates, successors, assigns and attorneys (the “Released Parties”), from any and all claims, actions, causes of action, sums of money due, suits, debts, liens, covenants, contracts, obligations, costs,
expenses, damages, judgments, agreements, promises, demands, claims for attorney’s fees and costs, or liabilities whatsoever, in law or in equity, which the Executive ever had or now has against the Released Parties, arising by reason of or in
any way connected with or which may be traced either directly or indirectly to the employment relationship which existed between the Company or any of its parents, subsidiaries, affiliates, or predecessors and the Executive, or the termination of
that relationship, that the Executive has, had or purports to have, from the beginning of time to the date of this Release, whether known or unknown, that now exists, no matter how remotely they may be related to the aforesaid employment
relationship including but not limited to claims for employment discrimination under federal or state law, except as provided in Paragraph 2; claims arising under Title VII of the Civil Rights Act, 42 U.S.C. § 2000(e), et
seq. or the Americans With Disabilities Act, 42 U.S.C. § 12101, et seq.; claims for statutory or common law wrongful discharge, including any claims arising under the Fair Labor Standards Act, 29 U.S.C. § 201, et
seq.; claims for attorney’s fees, expenses and costs; claims for defamation; claims for wages or vacation pay; claims for benefits, including any claims arising under the Executive Retirement Income Security Act, 29 U.S.C. § 1001,
et seq.; and provided, however, that nothing herein shall release the Company of its obligations to the Executive under the 

  
 21 








 
Employment Agreement, the RSA Agreement (as defined in the Employment Agreement), the SARA Agreement (as defined in the Employment Agreement), the Indemnification Agreement, dated as of
September 2, 2014 (the “Indemnification Agreement”), between the Company and the Executive or any other contractual obligations between the Company or its subsidiaries or affiliates and the Executive (including, without limitation,
any equity award agreement or indemnification agreement), or any indemnification obligations to the Executive under the Indemnification Agreement, Company’s certificate of incorporation, bylaws, operating agreement or other constituent document
or any federal, state or local law or otherwise. 
 2. Release of Claims Under Age Discrimination in Employment Act. Without
limiting the generality of the foregoing, the Executive agrees that by executing this Release, he has released and waived any and all claims he has or may have as of the date of this Release for age discrimination under the Age Discrimination in
Employment Act, 29 U.S.C. § 621, et seq. It is understood that the Executive has been advised to consult with an attorney prior to executing this Release; that he in fact has consulted a knowledgeable, competent attorney regarding
this Release; that he may, before executing this Release, consider this Release for a period of 21 calendar days; and that the consideration he receives for this Release is in addition to amounts to which he was already entitled. It is further
understood that this Release is not effective until seven calendar days after the execution of this Release and that the Executive may revoke this Release within seven calendar days from the date of execution hereof.  

The Executive agrees that he has carefully read this Release and is signing it voluntarily. The Executive acknowledges that he has had
21 days from receipt of this Release to review it prior to signing or that, if the Executive is signing this Release prior to the expiration of such 21-day period, the Executive is waiving his right to
review the Release for such full 21-day period prior to signing it. The Executive has the right to revoke this release within seven days following the date of its execution by him. However, if the Executive
revokes this Release within such seven-day period, no severance benefit will be payable to him under the Employment Agreement and he shall return to the Company any such payment received prior to that date. 

  
 22 








 THE EXECUTIVE HAS CAREFULLY READ THIS RELEASE AND ACKNOWLEDGES THAT IT CONSTITUTES A GENERAL
RELEASE OF ALL KNOWN AND UNKNOWN CLAIMS AGAINST THE COMPANY UNDER THE AGE DISCRIMINATION IN EMPLOYMENT ACT. THE EXECUTIVE ACKNOWLEDGES THAT HE HAS HAD A FULL OPPORTUNITY TO CONSULT WITH AN ATTORNEY OR OTHER ADVISOR OF HIS CHOOSING CONCERNING HIS
EXECUTION OF THIS RELEASE AND THAT HE IS SIGNING THIS RELEASE VOLUNTARILY AND WITH THE FULL INTENT OF RELEASING THE COMPANY FROM ALL SUCH CLAIMS. 
  

	
	  

	Name of Executive: Dirk A. Montgomery
	Date: [—], 20[—]



  
 23 








 EXHIBIT B 

RSA AGREEMENT 
 (ATTACHED)


  
 24 








 HEALTH INSURANCE INNOVATIONS, INC. 

LONG TERM INCENTIVE PLAN 

Restricted Stock Award Agreement 

You have been granted Restricted Stock (this “Award”) on the following terms and subject to the provisions of Attachment
A and the Long Term Incentive Plan (the “Plan”) of Health Insurance Innovations, Inc. (the “Company”). Unless defined in this Award (including Attachment A, this “Agreement”),
capitalized terms will have the meanings assigned to them in the Plan. In the event of a conflict among the provisions of the Plan, this Agreement and any descriptive materials provided to you, the provisions of the Plan will prevail. 

 

			
	Participant	  	Dirk A. Montgomery
		
	Number of Shares Underlying Award	  	150,000 Shares (to the extent not vested as of any applicable date, the “Restricted Shares”)
		
	Grant Date	  	September 2, 2014
	  
 Vesting Schedule
(subject to
Section 3 of Attachment A)

		
	Vesting	  	 Subject to Section 3 of Attachment A, the Restricted Shares shall vest and become non-forfeitable in four tranches, on the
following dates in the following amounts:
  
 September 2, 2015: 30,000

September 2, 2016: 30,000
 September 2, 2017: 30,000

September 2, 2018: 60,000









 Attachment A 

Restricted Stock Award Agreement 

Terms and Conditions 

Grant to: Dirk A. Montgomery 

Section 1. Grant of Restricted Stock Award. Subject to the terms and conditions of the Plan and this Agreement, the Company hereby
grants this Award to the Participant on the Grant Date on the terms set forth on the cover page of this Agreement, as more fully described in this Attachment A. This Award is granted under the Plan, which is incorporated herein by this
reference and made a part of this Agreement. 
 Section 2. Issuance of Shares. 

(a) The Restricted Shares shall be evidenced by entry into the register of members of the Company; provided, however, that the Committee may
determine that the Restricted Shares shall be evidenced in such other manner as it deems appropriate, including the issuance of a share certificate or certificates. In the event that any share certificate is issued in respect of the Restricted
Shares, such certificate shall (i) be registered in the name of the Participant, (ii) bear an appropriate legend referring to the terms, conditions and restrictions applicable to the Restricted Shares and (iii) be held in custody by
the Company. 
 (b) Voting Rights. The Participant shall have voting rights with respect to the Restricted Shares. 

(c) Dividends. All cash and other dividends and distributions, if any, that are paid with respect to the Restricted Shares shall be
paid to the Participant at the time that the portion of this Award to which such dividends or other distributions relate vests and becomes nonforfeitable. 

(d) Transferability. Unless and until the Restricted Shares become vested in accordance with this Agreement, the Restricted Shares
shall not be assigned, sold, transferred or otherwise be subject to alienation by the Participant, and any purported assignment, sale, transfer or other alienation not permitted hereunder shall be void. 

  
 A-1 








 (e) Section 83(b) Election. If the Participant chooses, the Participant may make an
election under Section 83(b) of the Code with respect to the Restricted Shares, which would cause the Participant currently to recognize income for U.S. federal income tax purposes in an amount equal to the excess (if any) of the Fair Market
Value of the Restricted Shares (determined as of the Grant Date) over the amount, if any, that the Participant paid for the Restricted Shares, which excess will be subject to U.S. federal income tax. The form for making a Section 83(b) election
is available from the Company at the address indicated in Section 4(a). The Participant acknowledges that (i) the Participant is solely responsible for the decision whether or not to make a Section 83(b) election, and the Company
is not making any recommendation with respect thereto, (ii) it is the Participant’s sole responsibility to timely file the Section 83(b) election within 30 days after the Grant Date, if the Participant decides to make such
election, and (iii) if the Participant does not make a valid and timely Section 83(b) election, the Participant will be required to recognize ordinary income at the time of vesting on any future appreciation on the Restricted Shares.

 (f) Withholding Requirements. The Company may withhold any tax (or other governmental obligation) that becomes due with respect to
the Restricted Shares (or any dividend or distribution thereon), and the Participant shall make arrangements satisfactory to the Company to enable the Company to satisfy all such withholding requirements. Notwithstanding the foregoing, the
Committee, in its sole discretion, may permit the Participant to satisfy any such withholding requirement by transferring to the Company pursuant to such procedures as the Committee may require, effective as of the date on which such requirement
arises, a number of vested Shares owned and designated by the Participant having an aggregate Fair Market Value as of such date that is equal to the minimum amount required to be withheld. If the Committee permits the Participant to satisfy any such
withholding requirement pursuant to the preceding sentence, the Company shall remit to the Internal Revenue Service and appropriate state and local revenue agencies, for the credit of the Participant, an amount of cash withholding equal to the Fair
Market Value of the Shares transferred to the Company as provided above. 

  
 A-2 








 Section 3. Accelerated Vesting and Forfeiture upon Termination of Service; Accelerated
Vesting Generally. 
 (a) Death, Disability, Termination Without Cause or Resignation For Good Reason. In the event of the
Participant’s Termination of Service at any time due to Termination Upon Death, Termination For Disability, Termination Without Cause or Resignation For Good Reason, the Restricted Shares shall fully vest and become 100% vested and
non-forfeitable on the Termination Date. For purposes of this Agreement, Cause, Disability, Termination Upon Death, Termination For Disability, Termination Without Cause, Resignation For Good Reason and Termination Date shall have the respective
meanings set forth in the Employment Agreement, dated as of September 2, 2014, by and between the Participant and the Company. 
 (b)
For Any Other Reason. In the event of the Participant’s Termination of Service at any time under circumstances not described in Section 3(a), the Restricted Shares shall be forfeited in their entirety without any payment to the
Participant. 
 (c) Change of Control. If the Participant holds Restricted Shares at the time a Change in Control occurs, the
Restricted Shares shall become 100% vested and non-forfeitable on the date of the Change in Control immediately prior to the consummation thereof. 

(d) Effect of Vesting. Subject to the provisions of this Agreement, upon the vesting of any of the Restricted Shares, the restrictions
under this Award with respect to such Shares shall lapse. Subject to any applicable Lock Up Agreement, such Shares shall be fully assignable, saleable and transferable by the Participant, and the Company shall deliver such Shares to the Participant
by transfer to the Depository Trust Company for the benefit of the Participant or by delivery of a share certificate registered in the Participant’s name and such transfer shall be evidenced in the register of members of the Company. 

Section 4. Change in Control. Without limiting the Committee’s power under the Plan, upon the occurrence of a Change in
Control, the Committee is authorized (but not obligated) to make adjustments to the terms and conditions of the Restricted Shares without the need for the consent of the Participant, including, without limitation, the following (or any combination
thereof): 
 (a) The Committee may provide for the continuation or assumption of the Restricted Shares and this Agreement by the acquiring
or successor entity (or parent thereof), including the 

  
 A-3 








 
Company if it is the surviving entity, or for the substitution of the Restricted Shares and this Agreement with a substitute award with terms comparable to the Restricted Shares and this
Agreement (in each case with appropriate adjustments as to the number and type of Shares (or other securities) underlying the Award or substitute award). The determination of such appropriate adjustments and comparability shall be made by the
Committee. 
 (b) The Committee may provide for the cancellation of all or any portion of the Restricted Shares for value (payable in the
form of cash, stock, securities, other property or any combination thereof) based upon the price per Share received or to be received by other stockholders of the Company in the Change in Control transaction. 

Section 5. Miscellaneous Provisions. 

(a) Notices. All notices, requests and other communications under this Agreement shall be in writing and shall be delivered in person
(by courier or otherwise), mailed by certified or registered mail, return receipt requested, or sent by facsimile transmission, as follows: 

if to the Company, to: 
  

			
	Health Insurance Innovations, Inc.
	15438 N. Florida Avenue, Suite 201
	Tampa, Florida 33613
	Attention:	  	Chief Executive Officer
	Telecopy:	  	(877) 376-5832

 with a copy to (which shall not constitute notice hereunder): 

 

			
	Health Insurance Innovations, Inc.
	15438 N. Florida Avenue, Suite 201
	Tampa, Florida 33613
	Attention:	  	General Counsel
	Telecopy:	  	(877) 376-5832

 if to the Participant, to the address that the Participant most recently provided to the Company, 

  
 A-4 








 or to such other address or facsimile number as such party may hereafter specify for the purpose by notice to the
other party hereto. All such notices, requests and other communications shall be deemed received on the date of receipt by the recipient thereof if received prior to 5:00 p.m. on a business day in the place of receipt. Otherwise, any such
notice, request or communication shall be deemed received on the next succeeding business day in the place of receipt. 
 (b) Entire
Agreement. This Agreement, the Plan and any other agreements referred to herein and therein and any attachments referred to herein or therein, constitute the entire agreement and understanding between the parties in respect of the subject matter
hereof and supersede all prior and contemporaneous arrangements, agreements and understandings, both oral and written, whether in term sheets, presentations or otherwise, between the parties with respect to the subject matter hereof. 

(c) Amendment; Waiver. No amendment or modification of any provision of this Agreement shall be effective unless signed in writing by
or on behalf of the Company and the Participant, except that the Committee may amend or modify this Agreement without the Participant’s consent in accordance with the provisions of the Plan or as otherwise set forth in this Agreement. No waiver
of any breach or condition of this Agreement shall be deemed to be a waiver of any other or subsequent breach or condition whether of like or different nature. Any amendment or modification of or to any provision of this Agreement, or any waiver of
any provision of this Agreement, shall be effective only in the specific instance and for the specific purpose for which made or given. 

(d) Assignment. Neither this Agreement nor any right, remedy, obligation or liability arising hereunder or by reason hereof shall be
assignable by the Participant. 
 (e) Successors and Assigns; No Third Party Beneficiaries. This Agreement shall inure to the benefit
of and be binding upon the Company and the Participant and their respective heirs, successors, legal representatives and permitted assigns. Nothing in this Agreement, expressed or implied, is intended to confer on anyone other than the Company and
the Participant, and their respective heirs, successors, legal representatives and permitted assigns, any rights, remedies, obligations or liabilities under or by reason of this Agreement. 

  
 A-5 








 (f) Counterparts. This Agreement may be signed in any number of counterparts, each of
which shall be an original, with the same effect as if the signatures thereto and hereto were upon the same instrument. 
 (g) Plan.
The Participant acknowledges and understands that material definitions and provisions concerning this Award and the Participant’s rights and obligations with respect thereto are set forth in the Plan. The Participant has read carefully, and
understands, the provisions of the Plan. 
 (h) Governing Law. The Agreement shall be governed by the laws of the State of Florida,
without application of the conflicts of law principles thereof. 
 (i) No Right to Continued Service. The granting of the Award
evidenced hereby and this Agreement shall impose no obligation on the Company or any Affiliate to continue the service of the Participant and shall not lessen or affect the right that the Company or any Affiliate may have to terminate the service of
the Participant. 
 (j) WAIVER OF JURY TRIAL. EACH OF THE PARTIES HERETO IRREVOCABLY WAIVES ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY
LEGAL PROCEEDING ARISING OUT OF OR RELATED TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED HEREBY. 
 [Signature Page Follows] 

  
 A-6 








 IN WITNESS WHEREOF, the parties have executed this Agreement as of the day and year first written
above. 
  

			
	HEALTH INSURANCE INNOVATIONS, INC.
		
	By:	 	  

		 	Michael W. Kosloske
		 	Chairman, President and Chief Executive
		 	Officer
	
	PARTICIPANT
	
	  

	Dirk A. Montgomery



  
 A-7 








 EXHIBIT C 

SARA AGREEMENT 
 (ATTACHED)


  
 25 








 HEALTH INSURANCE INNOVATIONS, INC. 

LONG TERM INCENTIVE PLAN 

Stock Appreciation Rights Award Agreement 

You have been granted Stock Appreciation Rights (this “Award”) on the following terms and subject to the provisions of
Attachment A and the Long Term Incentive Plan (the “Plan”) of Health Insurance Innovations, Inc. (the “Company”). Unless defined in this Award (including Attachment A, this
“Agreement”), capitalized terms will have the meanings assigned to them in the Plan. In the event of a conflict among the provisions of the Plan, this Agreement and any descriptive materials provided to you, the provisions of the
Plan will prevail. 
  

			
	Participant	  	Dirk A. Montgomery
		
	Number of Stock Appreciation Rights	  	175,000 (each a “SAR”)
		
	Exercise Price per SAR	  	$12.86
		
	Grant Date	  	September 2, 2014
		
	Expiration Date	  	September 2, 2021, subject to earlier termination under Section 2(d) of Attachment A.

 Vesting Schedule 

(subject to Section 2(c) and Section 2(d) of Attachment A) 

 

			
	Vesting	  	 Subject to Section 2(c) and Section 2(d) of Attachment A, the SARs shall vest and become non-forfeitable
in four tranches, on the following dates in the following amounts:
  
 September 2,
2015: 35,000
 September 2, 2016: 35,000
 September 2,
2017: 35,000
 September 2, 2018: 70,000









 Attachment A 

Stock Appreciation Rights Award Agreement 

Terms and Conditions 

Grant to: Dirk A. Montgomery 

Section 1. Grant of Stock Appreciation Rights. Subject to the terms and conditions of the Plan and this Agreement, the Company
hereby grants this Award to the Participant on the Grant Date on the terms set forth on the cover page of this Agreement, as more fully described in this Attachment A. This Award is granted under the Plan, which is incorporated herein by
this reference and made a part of this Agreement. 
 Section 2. Terms of SAR. 

(a) Generally. Subject to the terms and conditions of this Agreement and the Plan, each SAR constitutes an unfunded and unsecured
promise of the Company to deliver to Participant, at the time such SAR is validly exercised, an amount, payable in the form of Shares, equal to the excess of (i) the Fair Market Value of one Share on the date of exercise, over (ii) the
Exercise Price per SAR set forth on the cover page of this Agreement (the “Spread”). 
 (b) Exercisability. Subject
to the terms and conditions of this Agreement and the Plan, a SAR may be exercised only after if it has vested and become exercisable under Section 2(c) or Section 2(d)(ii), and only before it has expired or been terminated
under Section 2(d)(i), Section 2(d)(ii) or Section 2(d)(iii). 
 (c) Vesting, Generally. 

(i) Subject to Section 2(d), the SARs shall vest and become exercisable in accordance with the Vesting Schedule set forth on the
cover page of this Agreement. 
 (ii) If the Participant holds unvested SARs at the time a Change in Control occurs, the SARs shall become
100% vested and exercisable on the date of the Change in Control immediately prior to the consummation thereof. 

  
 A-1 








 (d) Accelerated Vesting; Termination. 

(i) Except as otherwise provided in this Section 2(d), all of the SARs shall terminate at 5:00 p.m., Eastern time, on the
Expiration Date set forth on the cover page of this Agreement, unless earlier terminated under subsections (ii) or (iii) below. 

(ii) In the event of the Participant’s Termination of Service at any time due to Termination Upon Death, Termination For Disability,
Termination Without Cause or Resignation For Good Reason, 100% of the SARs granted under this Agreement shall become vested and exercisable, and shall continue to be exercisable until 5:00 p.m., Eastern time, on the date that is one year after the
Termination Date and at such time any unexercised SARs shall terminate, cease to be exercisable and by automatically forfeited to the Company without consideration. For purposes of this Agreement, Cause, Disability, Termination Upon Death,
Termination For Disability, Termination Without Cause, Resignation For Good Reason and Termination Date shall have the respective meanings set forth in the Employment Agreement, dated as of September 2, 2014, by and between the Participant and
the Company. 
 (iii) In the event of the Participant’s Termination of Service at any time under circumstances not described in
Section 2(d)(ii), all of the SARs shall terminate simultaneously with the Termination of Service on the Termination Date, including to the extent that the SARs are otherwise vested and exercisable as of the Termination Date, and shall
automatically be forfeited to the Company without consideration, and, if otherwise vested and exercisable, shall cease to be exercisable. 
 For clarity, in
no event shall any SAR be exercisable after the Expiration Date set forth on the cover page of this Agreement. 
 (e)
Transferability. The SARs, and the Participant’s rights under this Agreement, shall not be assigned, sold, transferred or otherwise be subject to alienation by the Participant, other than by will or the law of descent and distribution,
and any purported assignment, sale, transfer or other alienation not permitted hereunder shall be void. During the Participant’s lifetime, the SARs shall be exercisable only by the Participant. 

  
 A-2 








 Section 3. Exercise. 

(a) When to Exercise. Except as otherwise provided in the Plan or this Agreement, the Participant (or in the case of exercise after the
Participant’s death or incapacity, the Participant’s guardian, legal representative, heir or legatee, as the case may be) may exercise his or her SARs that are then exercisable under Section 2, in whole or in part, by following
the procedures set forth in this Section 3. If partially exercised, the Participant (or in the case of exercise after the Participant’s death or incapacity, the Participant’s guardian, legal representative, heir or legatee, as
the case may be) may thereafter exercise the remaining unexercised portion of the SARs, to the extent that they are then exercisable under Section 2, by following the procedures set forth in this Section 3. 

(b) Election to Exercise. To exercise the SARs, the Participant (or in the case of exercise after the Participant’s death or
incapacity, the Participant’s guardian, legal representative, heir or legatee, as the case may be) must deliver to the Secretary of the Company (or his or her designee) a written notice (or notice through another previously approved method,
which could include a web-based or e-mail system) which sets forth the number of SARs being exercised, together with any additional documents as the Company may require. Each such notice must satisfy whatever then-current procedures apply to the
SARs and must contain such representations, warranties and covenants as the Company requires. If someone other than the Participant exercises the SARs, then such person must submit documentation reasonably acceptable to the Company verifying that
such person has the legal right to exercise the SARs. 
 (c) Date of Exercise. The SARs shall be deemed to be exercised on the
business day that the Company receives a fully executed and completed exercise notice. If an exercise notice is received on a day that is not a business day, or is received after 5:00 p.m., Eastern time, on a business day, then the SARs shall
be deemed to be exercised on the first business day immediately following the day such notice is received by the Company. 
 (d)
Settlement. Upon a valid exercise of SARs, the Participant shall be entitled to receive that number of Shares determined by dividing (i) (1) the total number of SARs then being exercised, multiplied by (2) the Spread on the
date of exercise, by (ii) the Fair Market Value of one Share on the date of exercise. 

  
 A-3 








 (e) Fractional Shares. No fractional Shares shall be issued upon exercise of SARs, and if
the number of Shares otherwise issuable under Section 3(d) upon an exercise of SARs includes a fraction of a Share, then upon such exercise the Participant shall be entitled to receive (i) the number of Shares determined under
Section 3(d), rounded down to the nearest whole Share, plus (ii) an amount of cash equal to the Fair Market Value of one Share on the date of exercise, multiplied by such fraction of a Share. 

(f) Withholding Requirements. The delivery of Shares upon settlement of SARs is conditioned on the Participant making arrangements
satisfactory to the Company to enable the Company to satisfy all tax (or other governmental obligation) withholding requirements. In the event that there is any such withholding requirement upon an exercise of SARs, the Committee may, in its sole
discretion and pursuant to such procedures as the Committee may require, permit the Participant to satisfy any such withholding requirement by having the Company withhold from the number of Shares otherwise issuable to the Participant upon such
exercise a number of Shares having an aggregate Fair Market Value equal to the minimum amount required to be withheld. If the Committee permits the Participant to satisfy any such withholding requirement pursuant to the preceding sentence, the
Company shall remit to the Internal Revenue Service and appropriate state and local revenue agencies, for the credit of the Participant, an amount of cash withholding equal to the Fair Market Value of the Shares withheld by the Company as provided
above. 
 (g) Compliance with Law and Regulations. The SARs, their exercise and the obligation of the Company to issue Shares in
settlement thereof are subject to all applicable federal and state laws, rules and regulations, including securities laws, to approvals by any government or regulatory agency as may be required, and to the rules, regulations and other requirements
of the stock market or exchange upon which the Shares are then quoted, traded or listed. The Participant may not exercise a SAR if such exercise would violate any securities laws or other applicable law, rule, regulation or requirement. 

Section 4. No Rights of Stockholder. A holder of a SAR, as such, shall not be entitled to vote or receive dividends or be deemed
the holder of the Shares underlying the SAR for any purpose, nor shall anything contained in this Agreement be construed to confer upon the holder 

  
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of a SAR, as such, any of the rights or obligations of a stockholder of the Company, unless and until Shares are actually issued to and held of record by such holder upon settlement of the SARs
following valid exercise thereof. 
 Section 5. Change in Control. Without limiting the Committee’s power under the Plan,
upon the occurrence of a Change in Control, the Committee is authorized (but not obligated) to make adjustments to the terms and conditions of the SARs without the need for the consent of the Participant, including, without limitation, the following
(or any combination thereof): 
 (a) The Committee may provide for the continuation or assumption of the SARs and this Agreement by the
acquiring or successor entity (or parent thereof), including the Company if it is the surviving entity, or for the substitution of the SARs and this Agreement with a substitute award with terms comparable to the SARs and this Agreement (in each case
with appropriate adjustments as to the Exercise Price and the number and type of Shares (or other securities) underlying the Award or substitute award). The determination of such appropriate adjustments and comparability shall be made by the
Committee. 
 (b) The Committee may provide for the cancellation of all or any portion of the SARs for their Intrinsic Value (payable in the
form of cash, stock, securities, other property or any combination thereof) based upon the price per Share received or to be received by other stockholders of the Company in the Change in Control transaction. If at the time of a Change in Control
such Intrinsic Value is equal to or less than zero (i.e., the Exercise Price of the SARs equals or exceeds the price per Share received or to be received by other stockholders of the Company in the Change in Control transaction), then the Committee
may provide for the cancellation of the SARs without the payment of any consideration therefor. 

  
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 Section 6. Miscellaneous Provisions. 

(a) Notices. All notices, requests and other communications under this Agreement (other than a notice of exercise, which shall be
provided in accordance with Section 3) shall be in writing and shall be delivered in person (by courier or otherwise), mailed by certified or registered mail, return receipt requested, or sent by facsimile transmission, as follows: 

if to the Company, to: 
 Health
Insurance Innovations, Inc. 
 15438 N. Florida Avenue, Suite 201 

Tampa, Florida, 33613 

Attention: Chief Executive Officer 

Telecopy: (877) 376-5832 
 with
a copy to (which shall not constitute notice hereunder): 
 Health Insurance Innovations, Inc. 

15438 N. Florida Avenue, Suite 201 

Tampa, Florida, 33613 

Attention: General Counsel 

Telecopy: (877) 376-5832 
 if to
the Participant, to the address that the Participant most recently provided to the Company, 
 or to such other address or facsimile number as such party
may hereafter specify for the purpose by notice to the other party hereto. All such notices, requests and other communications shall be deemed received on the date of receipt by the recipient thereof if received prior to 5:00 p.m. on a business
day in the place of receipt. Otherwise, any such notice, request or communication shall be deemed received on the next succeeding business day in the place of receipt. 

(b) Entire Agreement. This Agreement, the Plan and any other agreements referred to herein and therein and any attachments referred to
herein or therein, constitute the entire agreement and understanding between the parties in respect of the subject matter hereof and supersede all prior and contemporaneous arrangements, agreements and understandings, both oral and written, whether
in term sheets, presentations or otherwise, between the parties with respect to the subject matter hereof. 
 (c) Amendment; Waiver.
No amendment or modification of any provision of this Agreement shall be effective unless signed in writing by or on behalf of the Company and the 

  
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Participant, except that the Committee may amend or modify this Agreement without the Participant’s consent in accordance with the provisions of the Plan or as otherwise set forth in this
Agreement. No waiver of any breach or condition of this Agreement shall be deemed to be a waiver of any other or subsequent breach or condition whether of like or different nature. Any amendment or modification of or to any provision of this
Agreement, or any waiver of any provision of this Agreement, shall be effective only in the specific instance and for the specific purpose for which made or given. 

(d) Successors and Assigns; No Third Party Beneficiaries. This Agreement shall inure to the benefit of and be binding upon the Company
and the Participant and their respective heirs, successors, legal representatives and permitted assigns. Nothing in this Agreement, expressed or implied, is intended to confer on anyone other than the Company and the Participant, and their
respective heirs, successors, legal representatives and permitted assigns, any rights, remedies, obligations or liabilities under or by reason of this Agreement. 

(e) Counterparts. This Agreement may be signed in any number of counterparts, each of which shall be an original, with the same effect
as if the signatures thereto and hereto were upon the same instrument. 
 (f) Plan. The Participant acknowledges and understands that
material definitions and provisions concerning this Award and the Participant’s rights and obligations with respect thereto are set forth in the Plan. The Participant has read carefully, and understands, the provisions of the Plan. 

(g) Governing Law. The Agreement shall be governed by the laws of the State of Florida, without application of the conflicts of law
principles thereof. 
 (h) No Right to Continued Service. The granting of the Award evidenced hereby and this Agreement shall impose
no obligation on the Company or any Affiliate to continue the service of the Participant and shall not lessen or affect the right that the Company or any Affiliate may have to terminate the service of the Participant. 

  
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 (i) WAIVER OF JURY TRIAL. EACH OF THE PARTIES HERETO IRREVOCABLY WAIVES ANY AND ALL RIGHT
TO TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR RELATED TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED HEREBY. 
 [Signature
Page Follows] 

  
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 IN WITNESS WHEREOF, the parties have executed this Agreement as of the day and year first written
above. 
  

			
	HEALTH INSURANCE INNOVATIONS, INC.
		
	By:	 	  

		 	Michael W. Kosloske
		 	Chairman, President and Chief Executive
		 	Officer
	
	PARTICIPANT
	
	  

	Dirk A. Montgomery



  
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 EXHIBIT D 

INDEMNIFICATION AGREEMENT 

(ATTACHED) 

  
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