Second Amended and Restated Employment Agreement



 Exhibit 10.1 

SECOND AMENDED AND RESTATED EMPLOYMENT AGREEMENT 

THIS SECOND AMENDED AND RESTATED EMPLOYMENT AGREEMENT (this “Agreement”) is dated as of September 16, 2015 (the
“Effective Date”), by and between HEALTH INSURANCE INNOVATIONS, INC., a Delaware incorporated corporation (the “Company”), and MICHAEL D. HERSHBERGER (“Executive”).  

Recitals 
 A. The
Company and Executive previously entered into an Amended and Restated Employment Agreement, dated as of November 7, 2013, which was modified by that certain Letter Agreement, dated March 30, 2015 (collectively, the “Prior
Agreement”), under which Executive served most recently as Interim Chief Financial Officer of the Company. 
 B. The Company
and Executive desire that Executive begin to serve as Chief Financial Officer, Treasurer and Secretary of the Company in lieu of his prior position, upon the terms and conditions set forth herein. 

C. The Prior Agreement may be amended by the Company and Executive pursuant to and subject to Section 11 of thereof. 

D. This Agreement shall amend and restate the Prior Agreement in its entirety. 

E. 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) Effective as of the Effective Date, and during the Term (as defined below), Executive shall
serve as Chief Financial Officer, Treasurer and Secretary of the Company. In his capacity as Chief Financial Officer, 







 
Treasurer and Secretary, Executive shall (i) manage the financial reporting of the Company and have such authority and responsibilities as are consistent with the authority and
responsibilities of a Chief Financial Officer, Treasurer and Secretary of a publicly-traded company; (ii) be responsible for performing such other duties and exercising such other powers which the President or Chief Executive Officer of the
Company or the Board may from time-to-time assign to Executive; and (ii) report directly to the President of the Company. 
 (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 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. 

(c) The duties to be performed by Executive hereunder shall be principally performed at the Company’s corporate offices located in Tampa,
Florida, subject to reasonable travel requirements on behalf of the Company. Executive shall be entitled to annual paid time off of 20 days on the same terms that are applicable to other members of the Company’s senior management and 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 the first anniversary thereof. 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 (“Salary”), as compensation for the services
to be performed by Executive in his capacity as Chief Financial Officer, Treasurer and Secretary at the rate of $310,000 per calendar year. Executive’s Salary will be paid in accordance with the Company’s customary payroll procedures and
be subject to applicable taxes and withholdings. During the Term, the Board shall have the right to (at its discretion) increase, but not decrease, Executive’s Salary, except the Board may decrease Executive’s Salary in connection with a
base salary decrease that is generally applicable to all members of the Company’s senior management if such decrease is proportionate to the base salary decrease of all members of the Company’s senior management. Executive’s salary as
in effect from time to time shall constitute his “Salary” for purposes of this Agreement. 
 (b) On the earlier of the
Effective Date or the date approved by the Compensation Committee of the Board (the “Grant Date”), the Company shall execute and deliver to the Executive a Stock Appreciation Rights Award Agreement in the form attached hereto as Exhibit
B (the “SARA Agreement”), evidencing a grant to Executive pursuant to the terms of the Health Insurance Innovations, Inc. Long Term Incentive Plan (the “LTI Plan”) of 30,000 SARs (as defined in the SARA
Agreement). On the Grant Date, the Company shall also execute and deliver to the Executive a Restricted Stock Award Agreement in the form attached hereto as Exhibit C (the “RSA Agreement”), evidencing a grant to Executive
pursuant to the terms of the LTI Plan of 30,000 restricted shares of the Company’s Class A common stock (“Restricted Shares”). 

(c) Executive shall be paid a retention bonus in the amount of $50,000, subject to applicable taxes and withholdings on the date of
Executive’s first regular paycheck following the Effective Date. 
 (d) On each annual anniversary of the Effective Date, at the sole
discretion of the Board, Executive will be eligible for a target equity grant under the LTI Plan equal to 50% of Executive’s Salary then in effect as follows: (i) 1/3 of such grant in Restricted Shares and (ii) 2/3 of such grant in
SARs (as determined by the Black-Sholes option pricing model), with a strike price equal to the market closing price of the Company’s Class A common stock on the NASDAQ Global Market (or such other national securities exchange on which
such common stock is then traded) on the applicable grant date. These annual grants of Restricted Shares and SARs, if awarded, will vest 25% on each of the first two anniversaries of the applicable grant date and 50% on the third anniversary of the
applicable grant date. Annual awards of SARs under this Section 3.d will be in substantially the same form, and contain substantially the same terms and conditions, as the SARA Agreement 








 
attached hereto as Exhibit B (or such other award agreement as is made applicable to other members of the Company’s senior management) and annual awards of Restricted Shares under this
Section 3.d will be in substantially the same form, and contain substantially the same terms and conditions, as the form of Restricted Stock Award Agreement attached hereto as Exhibit C (or such other award agreement as is made
applicable to other members of the Company’s senior management). 
 (e) 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. 
 (f) 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 under the Company’s management bonus plan will be equal to 50% of Executive’s Salary then in effect; provided, that Executive will be paid a minimum bonus of $25,000 for calendar year 2015, which shall be paid
no later than March 15, 2016 (the “2015 Bonus”). 
 (g) 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 are applicable to other members of the Company’s senior management (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”); 
 (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, but including any notice from Executive to the Company pursuant to Section 2 that Executive has decided not to renew
the Term) sent to the Company from Executive stating that Executive is electing to terminate Executive’s employment with the Company absent a Good Reason Event (“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 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 President of the Company or
of 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 is 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 without Executive’s prior consent at a time when there are no circumstances pending that would permit the Board to terminate Executive for Cause, (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 is generally applicable to all members of the Company’s senior management) or (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) Patrick R. McNamee (“McNamee”) is not offered the position of Chief Executive Officer of the Company on or before December 31, 2015 and
there are no circumstances then pending that would permit the Company to terminate Executive for Cause; provided, that to constitute a “Good Reason Event” under this clause (iv), Executive must tender his resignation for such reason to the
Chief Executive Officer of the Company on the earlier of January 29, 2016 and the 30th day after Executive’s receipt of written notice from the Company that the Board has elected not to
promote McNamee to Chief Executive Officer of the Company. 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.” Notwithstanding anything to the contrary contained in this Agreement, the Prior Agreement or otherwise, none
of the execution of this Agreement, nor the consummation of the events contemplated by this Agreement (including without limitation, 







 
the cessation of Executive’s service as interim Chief Financial Officer of the Company), the commencement of Executive’s service as Chief Financial Officer, Treasurer and Secretary of
the Company, nor any other event, action or occurrence prior to the Effective Date shall constitute a Good Reason Event, Termination Without Cause or a Termination Date for purposes of this Agreement, the Prior Agreement or the RSA Agreement or SARA
Agreement. 
 (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 the Executive as of the Termination Date (the “Accrued Salary”); 

(B) Executive (or Executive’s legal representative) shall be entitled to receive in cash the 2015 Bonus, if same has not
then been previously disbursed; and 
 (C) 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”). 
 (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. In the event of Termination Without Cause or
Resignation For Good Reason pursuant to Section 4(a)(iv) or 4(a)(vi) of this Agreement, subject to Section 4(c)(ii) of this Agreement: 

(A) Executive (or Executive’s legal representative) shall be entitled to receive in cash an amount equal to the Accrued
Salary; 







 (B) Executive (or Executive’s legal representative) shall be entitled to
receive in cash the 2015 Bonus, if same has not then been previously disbursed; and 
 (C) Executive (or Executive’s
legal representative) shall be entitled to receive in cash an amount equal to any Accrued Bonus; and 
 (D) Executive (or
Executive’s legal representative) shall be entitled to receive in cash an amount equal to twelve (12) months of Executive’s Salary (at the rate then in effect, and without taking into account any reductions that would have given rise
to a Good Reason Event), payable in accordance with the Company’s customary payroll procedures commencing on the Termination Date and ending twelve (12) months thereafter. 

(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. 
 (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, subject to applicable taxes and withholdings. 
 (ii) As a condition to
the Company’s obligations, if any, to make any Accrued Bonus, 2015 Bonus and severance payments provided under Sections 4(b)(i)(B) and (C), 4(b)(iii)(B), (C) and (D), Executive (or Executive’s legal representative
in the case of death or Disability) 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) and (C), 4(b)(iii)(B), (C) and (D) of this Agreement during such times as Executive is in breach of Section 5 or Section 18 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. 
 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. 

(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 entity having a class of equity securities actively traded on a national securities exchange or on the
NASDAQ Global Market which represent, in the aggregate, not more than 1% of such entity’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 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 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 Company and
perform all actions reasonably necessary or requested by the Company (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), 5(c) or 5(d) of this Agreement, the Restricted Period shall be tolled until such breach or violation has been cured. 

(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 attorneys’ fees, expenses and disbursements. 

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 an 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:
President
 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

 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, including without limitation, the Prior Agreement. 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. Executive agrees that in the event of any dispute or claim arising under this Agreement, jurisdiction and
venue shall be vested and proper, and Executive hereby consents to the jurisdiction of any court sitting 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. 

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
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 subsidiary’s or affiliate’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 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 separate counterparts, any one 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] 







 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/ Patrick R. McNamee

		 	Name:	 	Patrick R. McNamee
		 	Title:	 	President
	
	EXECUTIVE
	
	 /s/ Michael D. Hershberger

	Michael D. Hershberger


 [SIGNATURE PAGE TO AMENDED AND RESTATED EMPLOYMENT AGREEMENT] 







 EXHIBIT A 

FORM OF RELEASE 

This RELEASE (“Release”) is granted effective as of the [●] day of
[●], 20[●] by MICHAEL D. HERSHBERGER (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 16, 2015, 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 



  
 20 









	 	
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 Employment Agreement,
the SARA Agreement or RSA Agreement (each as defined in the Employment Agreement), the Indemnification Agreement, dated as of September 16, 2015 (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 other equity award 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. 

  
 21 








 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: Michael D. Hershberger
	Date: [●], 20[●]



  
 22 








 Exhibit B 

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	  	Michael D. Hershberger
		
	Number of Stock Appreciation Rights	  	30,000 (each a “SAR”)
		
	Exercise Price per SAR	  	$4.99
		
	Grant Date	  	September 16, 2015
		
	Expiration Date	  	September 16, 2022, 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 three
tranches, on the following dates in the following amounts:
  
 September 16, 2016:
7,500

		  	September 16, 2017: 7,500
		  	September 16, 2018: 15,000








 Attachment A 

Stock Appreciation Rights Award Agreement 

Terms and Conditions 

Grant to: Michael D. Hershberger 

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     , 2015, 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 

  
 A-4 








 
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. 

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 

  
 A-5 








 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  

  
 A-6 








 
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. 

  
 A-7 








 (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] 

  
 A-8 








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

			
	HEALTH INSURANCE INNOVATIONS, INC.
		
	By:	 	  

		 	Patrick R. McNamee
		 	President
	
	PARTICIPANT
	
	  

	Michael D. Hershberger



  
 A-9 








 Exhibit C 

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	  	Michael D. Hershberger
		
	Number of Shares Underlying Award	  	30,000 Shares (to the extent not vested as of any applicable date, the “Restricted Shares”)
		
	Grant Date	  	September 16, 2015

 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 three tranches, on
the following dates in the following amounts:
  
 September 16, 2016: 25%

		  	September 16, 2017: 25%
		  	September 16, 2018: 50%








 Attachment A 

Restricted Stock Award Agreement 

Terms and Conditions 

Grant to: Michael D. Hershberger 

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     , 2015, 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:	 	  

		 	Name:	 	
		 	Title:	 	
	
	PARTICIPANT
	
	  

	Michael D. Hershberger



  
 A-7 








 Exhibit D 

INDEMNIFICATION AGREEMENT 
 This
Indemnification Agreement (this “Agreement”) is made effective as of September 16, 2015 by and between Health Insurance Innovations, Inc., a Delaware corporation (the “Corporation”) and Michael D. Hershberger
(“Indemnitee”). 
 WHEREAS, increased corporate litigation has subjected officers and directors to litigation risks and
expenses, and the limitations on the availability of director and officer liability insurance may make it increasingly difficult for the Corporation to attract and retain the most capable persons reasonably available to serve as officers and/or
directors of the Corporation; and 
 WHEREAS, the Corporation desires to provide Indemnitee with specific contractual assurance of
Indemnitee’s rights to full indemnification against litigation risks and expenses (regardless, among other things, of any amendment to or revocation of the Corporation’s Certificate of Incorporation (the “Certificate of
Incorporation”) or the Corporation’s Bylaws (the “Bylaws”) or the Operating Agreement of Health Plan Intermediaries Holdings, LLC (the “Operating Agreement”) or any change in the ownership of the
Corporation or the composition of its Board of Directors); and 
 WHEREAS, the Corporation intends that this Agreement provide Indemnitee
with greater protection than that which is provided by the Certificate of Incorporation and Bylaws; and 
 WHEREAS, Indemnitee’s
willingness to serve as an officer and/or director, as the case may be, of the Corporation is predicated, in substantial part, upon the Corporation’s willingness to indemnify him or her in accordance with the principles reflected above, to the
fullest extent permitted by the laws of the State of Delaware, and upon the other undertakings set forth in this Agreement; and 
 WHEREAS,
the indemnifications provisions set forth in this Agreement are not exclusive and thereby contemplate that contracts may be entered into between the Corporation and its directors, officers and other persons with respect to indemnification; and 

WHEREAS, in order to induce Indemnitee to serve as an officer and/or director, as the case may be, of the Corporation, the Corporation has
determined and agreed to enter into this Agreement with Indemnitee. 







 NOW, THEREFORE, in consideration of the mutual promises made in this Agreement, and for other
good and valuable consideration, the receipt of which is hereby acknowledged, the Corporation and Indemnitee hereby agree as follows: 
 1.
Indemnification. 
 (a) Third Party Proceedings. The Corporation shall indemnify Indemnitee if Indemnitee is or was a party or
is threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether civil, criminal, administrative or investigative (other than an action by or in the right of the Corporation) by reason of the fact that
Indemnitee is or was, or has agreed to become, an officer and/or director, as the case may be, of the Corporation, or any subsidiary of the Corporation, by reason of any actual or alleged error or misstatement or misleading statement made or
suffered by Indemnitee, by reason of any action or inaction on the part of Indemnitee while an officer and/or director, as the case may be, of the Corporation, or by reason of the fact that Indemnitee is or was serving at the request of the
Corporation as an officer and/or director, as the case may be, of another corporation, partnership, joint venture, trust or other enterprise (including without limitation employee benefit plans and administrative committees thereof), against
expenses (including reasonable attorneys’ fees and disbursements), damages (compensatory, exemplary, punitive or otherwise), costs of attachment or similar bonds, judgments, fines and amounts paid in settlement (if such settlement is approved
in advance by the Corporation, such approval not to be unreasonably withheld), in each case actually and reasonably incurred by Indemnitee in connection with such action, suit or proceeding if Indemnitee acted in good faith and in a manner
Indemnitee reasonably believed to be in or not opposed to the best interests of the Corporation, and, with respect to any criminal action or proceeding, had no reasonable cause to believe Indemnitee’s conduct was unlawful. The termination of
any action, suit or proceeding by judgment, order, settlement, conviction, or upon a plea of nolo contendere or its equivalent, shall not, of itself, create a presumption that Indemnitee did not act in good faith and in a manner which Indemnitee
reasonably believed to be in or not opposed to the best interests of the Corporation, or, with respect to any criminal action or proceeding, that Indemnitee had reasonable cause to believe that Indemnitee’s conduct was unlawful. 

(b) Proceedings by or in the Right of the Corporation. The Corporation shall indemnify Indemnitee if Indemnitee was or is a party or is
threatened to be made a party to any threatened, pending or completed action or proceeding by or in the right of the Corporation or any subsidiary of the Corporation to procure a judgment in its favor by reason of the fact that Indemnitee is or was,
or has agreed to become, an officer and/or director, as the case may be, of the Corporation, or any subsidiary of the Corporation, by reason of any actual or alleged error or misstatement or misleading statement made or suffered by Indemnitee, by
reason of any action or inaction on the part of Indemnitee while an officer and/or director, as the case may be, or by reason of the fact that Indemnitee is or was serving at the request of the Corporation as an officer and/or director, as the case
may be, of another corporation, partnership, joint venture, trust or other enterprise (including without limitation employee benefit plans and administrative committees thereof), against expenses (including reasonable attorneys’ fees and
disbursements), damages (compensatory, exemplary, punitive or otherwise), costs of attachment or similar bonds, judgments, fines and, to the fullest extent permitted by law, amounts paid in settlement (if such settlement is approved in advance by
the Corporation, such approval not to be unreasonably withheld), in each case to the extent actually and reasonably incurred by Indemnitee in connection with the defense or settlement of such action or suit if Indemnitee acted in good faith and in a
manner Indemnitee reasonably 

  
 2 








 
believed to be in or not opposed to the best interests of the Corporation and its stockholders, except that no indemnification shall be made in respect of any claim, issue or matter as to which
Indemnitee shall have been finally adjudicated by a final, unappealable order or judgment by a court having jurisdiction over the parties and the subject matter of the dispute from which no further right of appeal exists to be liable to the
Corporation in the performance of Indemnitee’s duty to the Corporation and its stockholders unless and only to the extent that the court in which such action or proceeding is or was pending shall determine upon application that, in view of all
the circumstances of the case, Indemnitee is fairly and reasonably entitled to indemnity for such expenses which such court shall deem proper. 

(c) Mandatory Payment of Expenses. To the extent that Indemnitee has been successful on the merits or otherwise in defense of any
action, suit or proceeding referred to in Section 1(a) or Section 1(b) or the defense of any claim, issue or matter therein, Indemnitee shall be indemnified against expenses (including reasonable attorneys’ fees and disbursements)
actually and reasonably incurred by Indemnitee in connection therewith. 
 (d) Witness. Notwithstanding any other provision of this
Agreement, to the extent that Indemnitee is, by reason of the fact that Indemnitee is or was an officer and/or director, as the case may be, of the Corporation or was serving at the request of the Corporation as an officer and/or director, as the
case may be, of another corporation, partnership, joint venture, trust or other enterprise (including without limitation employee benefit plans and administrative committees thereof), a witness in any action, suit or proceeding to which Indemnitee
is not a party, Indemnitee shall be indemnified against all expenses (including reasonable attorneys’ fees and disbursements) actually and reasonably incurred by Indemnitee in connection therewith. 

(e) Serving at the Request of the Corporation. For purposes of this Agreement, if Indemnitee should serve as an officer and/or
director, as the case may be, of another corporation, partnership, joint venture, trust or other enterprise (including without limitation employee benefit plans and administrative committees thereof) it will be conclusively presumed in the case of
any of the foregoing that are “affiliates” of the Corporation as defined in Rule 12b-2 under the Securities Exchange Act of 1934, as amended) that Indemnitee was serving at the request of the Corporation. 

2. Expenses, Indemnification Procedure. 

(a) Advancement of Expenses. The Corporation shall pay all expenses incurred by Indemnitee in connection with the investigation,
defense, settlement or appeal of any civil or criminal action, suit or proceeding referred to in Section l hereof (including amounts actually paid in settlement of any such action, suit or proceeding), as such expenses are incurred and in advance of
the final disposition of such action, suit or proceeding. Indemnitee hereby undertakes to repay such amounts advanced only if, and to the extent that, it shall ultimately be determined that Indemnitee is not entitled to be indemnified by the
Corporation as authorized hereby by a final, unappealable order or 

  
 3 








 
judgment by a court having jurisdiction over the parties and the subject matter of the dispute from which no further right of appeal exists. Indemnitee’s undertaking hereunder need not be
secured and shall be accepted without reference to Indemnitee’s financial ability to make repayment if and to the extent that it shall ultimately be determined as provided in this Agreement that Indemnitee is not entitled to be indemnified
under this Agreement or otherwise. 
 (b) Notice/Cooperation by Indemnitee. Indemnitee shall give the Corporation notice in writing
as soon as practicable of any claim made against Indemnitee for which indemnification will or could be sought under this Agreement; provided, however, that the omission so to notify an officer of the Corporation will not relieve the Corporation from
any obligation which it may have to Indemnitee under this Agreement or otherwise unless and only to the extent that such omission can be shown to have prejudiced the Corporation. Notice to the Corporation shall be directed to the Chief Executive
Officer of the Corporation and shall be given in accordance with the provisions of Section 9(d) below. In addition, Indemnitee shall give the Corporation such information and cooperation as it may reasonably require and as shall be within
Indemnitee’s power. 
 (c) Procedure. Any indemnification and advances provided for in Section 1 and this Section 2
shall be made no later than thirty (30) days after receipt of the written request of Indemnitee. If a claim under this Agreement, under any statute, or under any provision of the Certificate of Incorporation or Bylaws or the Operating Agreement
providing for indemnification, is not paid in full by the Corporation (or, in the case of the Operating Agreement, by Health Plan Intermediaries Holdings, LLC) within thirty (30) days after a written request for payment thereof has first been
received by the Corporation (or, if pursuant to the Operating Agreement, by Health Plan Intermediaries Holdings, LLC), Indemnitee may, but need not, at any time thereafter bring an action against the Corporation to recover the unpaid amount of the
claim and, subject to Section 8 of this Agreement, Indemnitee shall also be entitled to be paid for the expenses (including reasonable attorneys’ fees and disbursements) of bringing such action. It shall be a defense to any such action
(other than an action brought to enforce a claim for expenses incurred in connection with any action, suit or proceeding in advance of its final disposition) that Indemnitee has not met the standards of conduct which make it permissible under
applicable law for the Corporation to indemnify Indemnitee for the amount claimed, but in such case, it shall be presumed that Indemnitee has at all times acted in good faith and in a manner Indemnitee reasonably believed to be in or not opposed to
the best interests of the Corporation and the burden of proving such defense shall be on the Corporation. Indemnitee shall be entitled to receive interim payments of expenses pursuant to Section 2(a) unless and until such defense may be finally
adjudicated by a final, unappealable order or judgment by a court having jurisdiction over the parties and the subject matter of the dispute from which no further right of appeal exists. Indemnitee shall be presumed to have acted in good faith if
Indemnitee’s action is based on the records or books of account of the Corporation, including financial statements, or on information supplied to an Indemnitee by the officers of the Corporation in the course of their duties, or on the advice
of legal counsel for the Corporation or on information or records given or reports made to the Corporation by an 

  
 4 








 
independent certified public accountant or by an appraiser or other expert selected with reasonable care by the Corporation. In addition, the knowledge and/or actions, or failure to act, of any
director, officer, agent or employee of the Corporation, unless affiliated with Indemnitee, shall not be imputed to Indemnitee for purposes of determining the right to indemnification under this Agreement. Furthermore, the Corporation shall
conclusively be presumed to have entered into this Agreement and assumed the obligations imposed on it to induce Indemnitee to accept the position of, or to continue as an officer and/or director, as the case may be, of the Corporation. It is the
parties’ intention that if the Corporation contests Indemnitee’s right to indemnification, the question of Indemnitee’s right to indemnification shall be for the court to decide, and neither the failure of the Corporation (including
its Board of Directors, any committee or subgroup of the Board of Directors, independent legal counsel, or its stockholders) to have made a determination that indemnification of Indemnitee is proper in the circumstances because Indemnitee has met
the applicable standard of conduct required by applicable law, nor an actual determination by the Corporation (including its Board of Directors, any committee or subgroup of the Board of Directors, independent legal counsel, or its stockholders)
that Indemnitee has not met such applicable standard of conduct, shall create a presumption that Indemnitee has or has not met the applicable standard of conduct. 

(d) Notice to Insurers. If, at the time of the receipt of a notice of a claim pursuant to Section 2(b) hereof, the Corporation has
director and officer liability insurance in effect, the Corporation shall give prompt notice of the commencement of such proceeding to the insurers in accordance with the procedures set forth in the respective policies (unless Indemnitee’s
involvement in such proceeding is solely as a witness or there is otherwise no basis for asserting coverage). The Corporation shall thereafter take all necessary or desirable action to cause such insurers to pay, on behalf of the Indemnitee, all
amounts payable as a result of such proceeding in accordance with the terms of such policies. 
 (e) Selection of Counsel. In the
event the Corporation shall be obligated under Section 2(a) hereof to pay the expenses of any proceeding against Indemnitee, the Corporation, if appropriate, shall be entitled to assume the defense of such proceeding with counsel reasonably
satisfactory to Indemnitee, upon the delivery to Indemnitee of written notice of its election so to do. After delivery of such notice and the retention of such counsel by the Corporation, the Corporation will not be liable to Indemnitee under this
Agreement for any fees of counsel subsequently incurred by Indemnitee with respect to the same proceeding, provided that (i) Indemnitee shall have the right to employ counsel in any such proceeding at Indemnitee’s expense; and (ii) if
(A) the employment of counsel by Indemnitee has been previously authorized by the Corporation, (B) Indemnitee shall have reasonably concluded that there may be a conflict of interest between the Corporation and Indemnitee in the conduct of
any such defense, (C) the Corporation shall not, in fact, have employed counsel to assume the defense of such proceeding or (D) the Corporation is not financially or legally able to perform its indemnification obligations, then the fees
and expenses of Indemnitee’s counsel shall be at the expense of the Corporation. 

  
 5 








 (f) Settlement. The Corporation shall not settle any action or claim in any manner which
would impose any penalty or limitation on Indemnitee that would not be indemnifiable hereunder or for which indemnification would not be provided by the Corporation without Indemnitee’s written consent. 

3. Additional Indemnification Rights, Nonexclusivity, Contribution. 

(a) Scope. Notwithstanding any other provision of this Agreement, the Corporation hereby agrees to indemnify the Indemnitee to the
fullest extent permitted by law, notwithstanding that such indemnification is not specifically authorized by the other provisions of this Agreement, the Certificate of Incorporation, the Bylaws, the Operating Agreement or by statute. In the event of
any change, after the date of this Agreement, in any applicable law, statute, or rule which expands the right of a Delaware corporation to indemnify an officer or member of its board of directors, such changes shall be deemed to be within the
purview of Indemnitee’s rights and the Corporation’s obligations under this Agreement. In the event of any change in any applicable law, statute or rule which narrows the right of a Delaware corporation to indemnify an officer or member of
its board of directors, such changes, to the extent not otherwise required by such law, statute or rule to be applied to this Agreement shall have no effect on this Agreement or the parties’ rights and obligations hereunder. 

(b) Nonexclusively. The indemnification provided by this Agreement shall not be deemed exclusive of any rights to which Indemnitee may
be entitled under the Certificate of Incorporation, the Bylaws, any agreement (including the Operating Agreement), any vote of stockholders or disinterested members of the Corporation’s Board of Directors, the General Corporation Law of the
State of Delaware, or otherwise, both as to action in Indemnitee’s official capacity and as to action in another capacity while holding such office. The indemnification provided under this Agreement shall continue as to Indemnitee for any
action taken or not taken while serving in an indemnified capacity even though he or she may have ceased to serve in any such capacity at the time of any action, suit or other covered proceeding. 

(c) Contribution in Event of Joint Liability. 

(i) Subject to Section 1 hereof, in respect of any action, suit or proceeding in which the Corporation is jointly liable
with Indemnitee (or would be if joined in such action, suit or proceeding), the Corporation shall pay, in the first instance, the entire amount of any judgment or settlement of such action, suit or proceeding without requiring Indemnitee to
contribute to such payment and the Corporation hereby waives and relinquishes any right of contribution it may have against Indemnitee. The Corporation shall not enter into any settlement of any action, suit or proceeding in which the Corporation is
jointly liable with Indemnitee (or would be if joined in such action, suit or proceeding) unless such settlement provides for a full and final release of all claims asserted against Indemnitee. 

  
 6 








 (ii) If, for any reason, Indemnitee shall elect or be required to pay all or any
portion of any judgment or settlement in any action, suit or proceeding in which the Corporation is jointly liable with Indemnitee and for which the Corporation would otherwise be obligated to indemnify Indemnitee under this Agreement, the
Corporation shall, to the extent permitted by applicable law, contribute to the amount of such indemnifiable losses, judgments, fines and amounts paid in settlement (if such settlement is approved in advance in writing by the Corporation, which
approval shall not be unreasonably withheld) actually and reasonably incurred and paid or payable by Indemnitee in proportion to the relative benefits received by the Corporation and all officers, directors or employees of the Corporation other than
Indemnitee, on the one hand, and Indemnitee, on the other hand, from the transaction from which such action, suit or proceeding arose; provided, however, that the proportion determined on the basis of relative benefit may, to the extent necessary to
conform to law, be further adjusted by reference to the relative fault of the Corporation and all officers, directors or employees of the Corporation other than other indemnitees who are jointly liable with Indemnitee, on the one hand, and all
indemnitees, including Indemnitee, on the other hand, in connection with the events that resulted in such indemnifiable losses, judgments, fines or settlement amounts, as well as any other equitable considerations which the law may require to be
considered. The relative fault of the Corporation and all officers, directors or employees of the Corporation, other than Indemnitee, on the one hand, and Indemnitee, on the other hand, shall be determined by reference to, among other things, the
degree to which their actions were motivated by intent to gain personal profit or advantage, the degree to which their liability is primary or secondary and the degree to which their conduct is active or passive. 

(iii) The Corporation hereby agrees to fully indemnify and hold Indemnitee harmless from any claims of contribution which may
be brought by officers, directors or employees of the Corporation who may be jointly liable with Indemnitee. 
 4. Partial Indemnification. If
Indemnitee is entitled under any provision of this Agreement to indemnification by the Corporation for some or a portion of the expenses, judgments, fines or penalties actually or reasonably incurred in the investigation, defense, appeal or
settlement of any civil or criminal action, suit or proceeding, but not, however, for the total amount thereof, the Corporation shall nevertheless indemnify Indemnitee for the portion of such expenses, judgments, fines or penalties to which
Indemnitee is entitled. If Indemnitee is not wholly successful in an action, suit or proceeding but is successful, on the merits or otherwise, as to one or more but less than all claims, issues or matters in such action, suit or proceeding, the
Company shall indemnify Indemnitee for all indemnifiable losses actually and reasonably incurred by Indemnitee or on Indemnitee’s behalf in connection with each successfully resolved claim, issue or matter. For purposes of this Section 4
and without limitation, the termination of any claim, issue or matter in such an action, suit or proceeding by dismissal, with or without prejudice, shall be deemed to be a successful result as to such claim, issue or matter. 

  
 7 








 5. Mutual Acknowledgment. Both the Corporation and the Indemnitee acknowledge that in certain instances,
Federal law or applicable public policy may prohibit the Corporation from indemnifying its officers and directors under this Agreement or otherwise. Indemnitee understands and acknowledges that the Corporation may be required in the future to
undertake to the Securities and Exchange Commission to submit the question of indemnification to a court in certain circumstances for a determination of the Corporation’s right under public policy to indemnify Indemnitee and, in that event, the
Indemnitee’s rights and the Corporation’s obligations hereunder shall be subject to that determination. 
 6. Director and Officer Liability
Insurance. The Corporation shall, from time to time, make the good faith determination whether or not it is practicable for the Corporation to obtain and maintain a policy or policies of insurance with a reputable insurance corporation providing
the Indemnitee with coverage for losses from wrongful acts, and to ensure the Corporation’s performance of its indemnification obligations under this Agreement. In all policies of director and officer liability insurance, Indemnitee shall be
named as an insured in such a manner as to provide Indemnitee the same rights and benefits as are accorded to the most favorably insured of the Corporation’s officers and directors. Notwithstanding the foregoing, the Corporation shall have no
obligation to obtain or maintain such insurance if the Corporation determines in good faith that such insurance is not reasonably available, if the premium costs for such insurance are disproportionate to the amount of coverage provided, if the
coverage provided by such insurance is limited by exclusions so as to provide an insufficient benefit, or if Indemnitee is covered by similar insurance maintained by a parent or subsidiary of the Corporation. The Corporation shall not be liable
under this Agreement to make any payment of amounts otherwise indemnifiable hereunder if and to the extent that Indemnitee has otherwise actually received such payment under any insurance policy, contract, agreement or otherwise. 

7. Severability. Nothing in this Agreement is intended to require or shall be construed as requiring the Corporation to do or fail to do any act in
violation of applicable law. The Corporation’s inability, pursuant to court order, to perform its obligations under this Agreement shall not constitute a breach of this Agreement. The provisions of this Agreement shall be severable as provided
in this Section 7. If this Agreement or any portion hereof shall be invalidated on any ground by any court of competent jurisdiction, then the Corporation shall nevertheless indemnify Indemnitee to the full extent permitted by any applicable
portion of this Agreement that shall not have been invalidated, and the balance of this Agreement not so invalidated shall be enforceable in accordance with its terms. 

8. Exceptions. Any other provision herein to the contrary notwithstanding, the Corporation shall not be obligated pursuant to the terms of this
Agreement: 
 (a) Claims Initiated by Indemnitee. To indemnify or advance expenses to Indemnitee with respect to proceedings or
claims initiated or brought voluntarily by Indemnitee and not by way of defense, except with respect to proceedings brought to 

  
 8 








 
establish or enforce a right to indemnification under this Agreement or any other statute or law or otherwise as required under Section 145 of the Delaware General Corporation Law, but such
indemnification or advancement of expenses may be provided by the Corporation in specific cases if the Board of Directors finds it to be appropriate; 

(b) Lack of Good Faith. To indemnify Indemnitee for any expenses incurred by Indemnitee with respect to any proceeding instituted by
Indemnitee to enforce or interpret this Agreement, if a court having jurisdiction over the parties and the subject matter of the dispute determines by a final, unappealable order or judgment from which no further right of appeal exists, that each of
the material assertions made by Indemnitee in such proceeding was not made in good faith or was frivolous; or 
 (c) Claims Under
Section 16(b). To indemnify Indemnitee for expenses or the payment of profits on account of any suit in which a final, unappealable decision is rendered by a court having jurisdiction over the parties and the subject matter of the dispute
for an accounting of profits made from the purchase and sale by Indemnitee of securities of the Corporation in violation of Section 16(b) of the Securities Exchange Act of 1934, as amended, or any similar successor statute. 

9. Miscellaneous. 
 (a) Governing
Law. This Agreement shall be construed under and enforced in accordance with the internal substantive laws of the State of Delaware. Any litigation arising out of or incidental to this Agreement shall be initiated only in a court of competent
jurisdiction located within the State of Delaware. Each party hereby consents to the personal jurisdiction of the State of Delaware, acknowledges that venue is proper in any state or Federal court in the State of Delaware, agrees that any action
related to this Agreement must be brought in a state or Federal court in the State of Delaware and waives any objection that may exist, now or in the future, with respect to any of the foregoing. 

(b) Entire Agreement; Enforcement of Rights. This Agreement sets forth the entire agreement and understanding of the parties relating
to the subject matter herein and merges all prior discussions and agreements between them. No modification of or amendment to this Agreement, nor any waiver of any rights under this Agreement, shall be effective unless in writing signed by the
parties to this Agreement. The failure by either party to enforce any rights under this Agreement shall not be construed as a waiver of any rights of such party. 

(c) Construction. This Agreement is the result of negotiations between and has been reviewed by each of the parties hereto and their
respective counsel, if any; accordingly, this Agreement shall be deemed to be the product of all of the parties hereto, and no ambiguity shall be construed in favor of or against any one of the parties hereto. 

(d) Notices. All notices, requests, demands and other communications hereunder shall be in writing and shall be deemed to have been
duly given on the date of 

  
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personal delivery; or on the date of electronic confirmation of receipt, if sent by telecopier; or three (3) days after deposit in the United States mail, if mailed by certified or
registered mail, return receipt requested (postage prepaid); or one (1) day after delivery by a reputable overnight courier (delivery charges prepaid), as follows: 

(i) If to Indemnitee, to the address set forth below Indemnitee’s signature hereto. 

(ii) If to the Corporation, to: 

Health Insurance Innovations, Inc. 

15438 N. Florida Avenue, Suite 201 

Tampa, Florida 33613 

Attention: Chief Executive Officer 

Fax: (877) 376-5832 
 with
a copy sent at the same time and by the same means to: 
 Health Insurance Innovations, Inc. 

15438 N. Florida Avenue, Suite 201 

Tampa, Florida 33613 

Attention: General Counsel 

Fax: (877) 376-5832 
 or to such other
address as may have been furnished to Indemnitee by the Corporation or to the Corporation by Indemnitee, as the case may be. 
 (e)
Counterparts. This Agreement may be executed in two or more counterparts, each of which shall be deemed an original and all of which together shall constitute one instrument. 

(f) Successors and Assigns. This Agreement shall be binding upon the Corporation and its successors and assigns, and inure to the
benefit of Indemnitee and Indemnitee’s heirs, legal representatives and assigns. 
 (g) Modification and Waiver. No supplement,
modification, termination or amendment of this Agreement shall be binding unless executed in writing by both of the parties hereto. No waiver of any of the provisions of this Agreement shall be deemed or shall constitute a waiver of any other
provisions hereof (whether or not similar) nor shall such waiver constitute a continuing waiver. 
 (h) Subrogation. In the event of
payment under this Agreement, the Corporation shall be subrogated to the extent of such payment to all of the rights of recovery of Indemnitee, who shall execute all documents required and shall do all acts that may be necessary to secure such
rights and to enable the Corporation to effectively bring suit to enforce such rights. 

  
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 IN WITNESS WHEREOF, the parties hereto have executed this Indemnification Agreement as an
instrument under seal as of the day and year set forth on the first page of this Agreement. 
  

	
	HEALTH INSURANCE INNOVATIONS, INC.
	
	  

	Patrick R. McNamee
	President
	
	INDEMNITEE:
	
	  

	Michael D. Hershberger
	  

	  



  
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