Document:

Form of Employment Agreement

 Exhibit 10.15 
 Form of Agreement 
 EMPLOYMENT AGREEMENT 

THIS EMPLOYMENT AGREEMENT (this “Agreement”) is dated as of
             [·], 2013, by and between Health Insurance,
Innovations, Inc., a Delaware incorporated corporation (the “Company”), and Michael D. Hershberger (“Executive”). 
 Recitals 
 A. In connection with its Offering (the
“Offering”), as defined in Section 2, the Company intends to enter into this employment agreement with Executive, and Executive desires to be hired by the Company, upon the terms and conditions set forth herein, to become
effective on the consummation of the Offering; and 
 C. The Company and Executive agree to protect the interests of the Company
and Company’s customers and Confidential Information that may have been or that may be disclosed to Executive as set forth herein. 
 Agreement 
 NOW, THEREFORE, in consideration of the mutual promises made
herein and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the Parties, intending to be legally bound, agree as follows: 
 Section 1. Employment, Duties and Acceptance.  
 (a) The Company shall
employ Executive during the Term (as defined below) as Chief Financial Officer, Treasurer and Secretary. Executive shall have such authority and responsibilities as are consistent with the authority and responsibilities of a Chief Financial Officer,
Treasurer and Secretary in the health insurance products industry. 
 (b) Executive hereby accepts such employment and agrees 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 hereof, Executive will faithfully perform the duties assigned by the Company to the best of Executive’s ability. Executive further agrees to accept election and to serve during all or any part of the Term as an
officer, director or representative of any subsidiary or affiliate of the Company, without any compensation therefor other than that specified in this Agreement. Executive shall report directly to the Company’s Chief Executive Officer.

 (c) The duties to be performed by Executive hereunder shall be performed primarily at the
Company’s principal offices in Tampa, Florida subject to reasonable travel requirements on behalf of the Company. Executive shall be entitled to an annual vacation of 22 days 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 as of the consummation date of an underwritten initial public offering of not less than 4,000,000
shares of Company Class A common stock not later than June 1, 2013 (such date of consummation, the “Effective Date”), and such offering, the “Offering”, and ending on December 31, 2013. 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, following the end of the Term, the Company
shall pay to Executive an amount equal to one-twelfth of Executive’s annual Salary hereunder (at the rate then in effect) payable monthly in accordance with the Company’s existing payroll practices for the period commencing on the
Termination Date and ending 12 months after the Termination Date. As a condition to the Company’s obligations, if any, to make severance payments under this Section 2, Executive shall have executed, delivered and revoked a general release
in the form attached hereto as Exhibit A. For the avoidance of doubt, this Agreement shall have no force or effect until the Effective Date. 
 Section 3. Compensation. Executive shall be entitled to the following compensation: 
 (a) The Company agrees to pay to Executive a salary in cash (the “Salary”), as compensation for the services to be performed by Executive, at the rate of $200,000 per calendar year, paid
in accordance with the Company’s customary payroll procedures and subject to customary withholding. During the Term, the Board shall have the right to increase, but not decrease, the Salary. Executive’s salary as in effect from time to
time shall constitute the “Salary” for purposes of this Agreement. 

  
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 (b) 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. 
 (c) (i) The Company shall use its
best efforts to cause the grant to Executive [under a compensatory equity incentive plan to be adopted by the Company prior to the Effective Date] of              restricted shares of the
Company’s Class A Common Stock, vesting, as set forth below, subject in each case to Executive’s continued employment on the relevant vesting date: 
  

			
	 Number of Shares
	  	 Vesting Date

	 [10%]
	  	[Six month anniversary of Effective Date]
	 [10%]
	  	[First anniversary of Effective Date]
	 [10%]
	  	[Second anniversary of Effective Date]
	 [10%]
	  	[Third anniversary of Effective Date]
	 [10%]
	  	[Fourth anniversary of Effective Date]
	 [50%]
	  	[Fifth anniversary of Effective Date]

 (ii) Executive shall be eligible to participate in any equity incentive plan to be adopted in connection
with the Offering, in accordance with its terms. Executive shall be eligible for an annual bonus and long term incentive awards as determined at the sole discretion of the Company’s board of directors (the “Board”). 

(d) Executive shall be entitled to all rights and benefits for which Executive shall be eligible under any retirement, retirement
savings, profit-sharing, pension or welfare benefit plan, life, disability, health, dental, hospitalization and other forms of insurance and all other so-called “fringe” benefits or perquisites (except for with respect to any plan that
provides severance or other similar benefits), on the same terms that the Company provides to any other similarly situated senior Company executive (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”); 

  
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 (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, which notice can be given by the Company at any time after the Effective Date at the Company’s sole discretion, for any reason or for no reason (“Termination Without Cause”); 

(v) the effective date of a notice (other than a notice delivered pursuant to Section 4(a)(vi) of this Agreement)
sent to the Company from Executive stating that Executive is electing to terminate Executive’s employment with the Company without Good Reason (“Resignation Without Good Reason”); or 

(vi) the effective date of a written notice to Company stating Executive’s determination, made in good faith, that a
Good Reason Event (as defined below) has occurred within 30 days preceding such notice and as a consequence Executive is electing to terminate Executive’s employment hereunder for Good Reason (“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 

  
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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 directives of the Company, which, if capable of being cured shall not have been cured, within 5 days after
the Company shall have advised Executive in writing of its intention to terminate Executive’s employment, (vi) serious neglect or misfeasance by Executive in performance of Executive’s duties that, in the reasonable judgment of the
Board, has resulted in, or may reasonably be expected to have, an adverse effect on the business or reputation of the Company or any of its subsidiaries or affiliates, or (vii) material non-compliance with the terms of this Agreement.

 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 are 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. 
 (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) and 4(a)(ii) of this Agreement, Executive (or Executive’s legal representative) shall be entitled to receive in cash the following: 
 (A) an amount equal to any earned but unpaid Salary owing by the Company to Executive as of the Termination Date (the “Accrued Salary”), and 

(B) to the extent set forth in any written 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”). 

Nothing contained herein shall be deemed to limit or abrogate any insurance or other similar benefits available to Executive. 

  
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 (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 Sections 4(a)(iv) and 4(a)(vi) of this
Agreement, Executive shall be entitled to receive in cash, subject to Section 4(c)(ii) of this Agreement: 

(A) an amount equal to any Accrued Salary; 

(B) an amount equal to any Accrued Bonus; and 

(C) an amount equal to one-twelfth of Executive’s annual Salary hereunder (at the rate then in effect) payable
monthly for the period commencing on the Termination Date and ending 12 months after the Termination Date. 

(iv) Resignation Without Good Reason. In the event of Resignation Without Good Reason pursuant to
Section 4(a)(v) of this Agreement, Executive shall be entitled to receive in cash an amount equal to any Accrued Salary. 
 (v) Upon Termination For Any Reason. In the event of any termination, Executive shall be entitled to receive: 

(A) any unpaid reasonable, reimbursable business expenses incurred by Executive in the course of performing
Executive’s duties under this Agreement that were incurred in a manner consistent with the Company’s policies in effect from time to time with respect to travel, entertainment and other business expenses, subject to the Company’s
requirements with respect to incurring, reporting and documenting such expenses; and 
 (B) benefits under the
Company’s benefit plans of general application as shall be determined under the provisions of those plans. 
 (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. 

  
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 (ii) As a condition to the Company’s obligations, if any, to make any
Accrued Bonus and severance payments provided under this Section 4, Executive shall have executed, delivered and not revoked a general release in the form attached hereto as Exhibit A. 

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

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

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

 Section 5. Noncompetition, Nonsolicitation And Confidentiality. 

(a) Definitions. 

“Company’s Business” means (i) developing and administering web-based individual health insurance plans and
ancillary health insurance products, (ii) designing and structuring data-driven insurance products on behalf of the Company’s insurance carrier, (iii) marketing insurance products through the Company’s distribution networks,
(iv) managing member relations through the Company’s technology platform, and (v) any other business or commercial activity conducted on or after the Effective Date, in each case as conducted by the Company or any subsidiary or
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 

  
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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 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 corporation having a class of equity securities actively traded on a national securities exchange or on the Nasdaq Stock Market which represent, in the
aggregate, not more than 1% of such corporation’s fully-diluted shares. 
 (c) Nonsolicitation of Employees.
Executive covenants and agrees that during the Restricted Period, Executive will not, directly or indirectly, employ or solicit, or receive or accept the performance of services by any then current officer, manager, employee or independent
contractor of the Company or any subsidiary or affiliate of the Company, or in any way interfere with the relationship between the Company or any subsidiary or affiliate of the Company, on the one hand, and any such officer, manager, employee or
independent contractor, on the other hand. 
 (d) Nonsolicitation of Customers and Vendors. Executive covenants and
agrees that during the Restricted Period, Executive will not, directly or indirectly, induce, or attempt to induce, any customer, salesperson, distributor, supplier, vendor, manufacturer, representative, agent, jobber, licensee or other person
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 

  
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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 

  
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information (whether or not patentable) that relate to the Company’s or any of its subsidiary’s or affiliate’s 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 Board and perform all actions reasonably necessary or requested by the Board (whether during or after the Term) to establish and confirm such
ownership (including, without limitation, executing assignments, consents, powers of attorney and other instruments). 
 (h)
Miscellaneous. 
 (i) Executive acknowledges that (x) Executive’s position is a position of
trust and responsibility with access to Confidential Information of the Company, (y) the Confidential Information, and the relationship between the Company and each of its employees, Customers and Vendors, are valuable assets of the Company and
may not be converted to Executives own use and (z) the restrictions contained in this Section 5 are reasonable and necessary to protect the legitimate business interests of the Company and will not impair or infringe upon Executive’s
right to work or earn a living after Executive’s employment with the Company ends. 
 (ii) Each of the
foregoing obligations shall be enforceable independent of any other obligation, and the existence of any claim or cause of action that Executive may have against the Company, whether predicated on this Agreement or otherwise, shall not constitute a
defense to the enforcement by the Company of these obligations. 
 (iii) Executive acknowledges that monetary
damages will not be an adequate remedy for the Company in the event of a breach of this Agreement and that it would be impossible for the Company to measure damages in the event of such a breach. Therefore, Executive agrees that, in addition to
other rights that the Company may have at law or equity, the Company is entitled, without posting bond, to an injunction preventing Executive from any breach of this Agreement. 

(iv) In the event of a breach or violation by Executive during the Restricted Period of any restriction in
Section 5(b), (b) or (d) of this Agreement, the Restricted Period shall be tolled until such breach or violation has been cured. 
 (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

  
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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) 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 

  
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hereunder in accordance with the Company’s by-laws to the extent provided for any other officer or member of the Board of the Company. The Company’s obligations under this
Section 9 shall survive any termination of this Agreement or Executive’s employment hereunder. 
 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: Michael Hershberger
 Telecopy: (877)
376-5832

		  	with a copy to (which shall not constitute notice hereunder): Gary Raeckers
		
	 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. 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 irrespective of the fact that the parties now or at any time may be residents of or engage in activities in a different state. Employee agrees that in the event of any dispute or
claim arising under this Agreement, jurisdiction and venue shall be vested and proper, and Employee hereby consents to the jurisdiction of any court sitting in the State of Florida, including a federal district court. 

  
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 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

  
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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 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. The Company agrees that it will instruct each of its officers and members of its managing board not to make any disparaging communication regarding Executive, and no director, officer or employee of the
Company will be authorized on the Company’s behalf to make any such disparaging communications regarding Executive. 

Section 19. Recoupment. If the Company is required to prepare an accounting restatement due to the material noncompliance of
the Company, as a result of misconduct, with any financial reporting requirement under the securities laws, and if the Executive knowingly or grossly negligently engaged in the misconduct, or knowingly or grossly negligently failed to prevent the
misconduct, or if the Executive is one of the individuals subject to automatic forfeiture under, Section 304 of the United States Sarbanes-Oxley Act of 2002 (and not otherwise exempted), the Executive shall reimburse the Company the amount of
any payment in settlement of any earned or accrued during the twelve-month period following the first public issuance or filing with the United States Securities and Exchange Commission (whichever first occurred) of the financial document not in
compliance with such financial reporting requirement. Such payments shall be subject to repayment to or recoupment (clawback) by the Company in accordance with such policies and procedures as the Committee or Board may adopt from time to time,
including policies and procedures to implement applicable law (including. but not limited to Section 954 of the Dodd-Frank Act), stock market or exchange rules and regulations or accounting or tax rules and regulations. 

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

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

			
	HEALTH INSURANCE
    INNOVATIONS, INC.
		
	By:	 	  

	Name:	 	
	Title:	 	
	
	EXECUTIVE
	
	  

	Michael D. Hershberger

 [SIGNATURE PAGE TO EMPLOYMENT AGREEMENT] 

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

			
	HEALTH INSURANCE
    INNOVATIONS, INC.
		
	By:	 	  

	Name:	 	
	Title:	 	
	
	EXECUTIVE
	
	  

	Michael D. Hershberger

 [SIGNATURE PAGE TO EMPLOYMENT AGREEMENT] 

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

  
 [SIGNATURE
PAGE TO EMPLOYMENT AGREEMENT] 

 
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. 
 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:
		
	Date:	 	

  
 18Form of Restricted Stock Award Agreement

 Exhibit 10.21 
 Form of Agreement 
 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 agreement (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	  	[·] Shares (to the extent not vested as of any
applicable date, the “Restricted Shares”)
		
	Grant Date	  	[·], 2013
	
	 Vesting Schedule
 (subject to Section 3 of Attachment A)

		
	Vesting	  	Subject to Section 3 of Attachment A, 20% of the Restricted Shares shall vest and become non-forfeitable on the six-month anniversary of the Grant Date, with the balance vesting and
becoming non-forfeitable in four equal tranches on the first day of October, 2013, 2014, 2015 and 2016.

 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 not have voting rights with respect to the Restricted Shares. 

(c) Dividends. The Participant shall not have dividend rights with respect to the Restricted Shares. 

(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. 
 (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)

  
 A-1

 
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.

 Section 3. Accelerated Vesting and Forfeiture upon Termination of Service. 

(a) Death, Disability, without Cause or for Good Reason. In the event of the Participant’s Termination of Service at any time
due to the Participant’s death or Disability, by the Company or any Affiliate without Cause or by the Participant’s Resignation for Good Reason, the Restricted Shares shall fully vest and become non-forfeitable on the date of any such
termination. For purposes of this Agreement, Cause and Resignation for Good Reason shall have the respective meanings set forth in the Employment Agreement 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) 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. 

  
 A-2

 Section 4. 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: Michael W. Kosloske 

Telecopy: (877) 376-5832 
 with a copy to (which shall not constitute notice hereunder): 
 Gary Raeckers

 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 parties 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. 

  
 A-3

 (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.

 (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 such 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. 

  
 A-4

 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
		
		 	  

		 	Name:

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