X0306 4 2019-06-04 0001561387 Health Insurance Innovations, Inc. HIIQ 0001569146 Kosloske Michael W 16221 VILLARREAL DE AVILA TAMPA FL 33613 true 0001571686 Health Plan Intermediaires, LLC C/O HEALTH INSURANCE INNOVATIONS, INC. 15438 N. FLORIDA AVENUE, SUITE 201 TAMPA FL 33613 true 0001571685 Health Plan Intermediaries Sub, LLC C/O HEALTH INSURANCE INNOVATIONS, INC. 15438 N. FLORIDA AVENUE, SUITE 201 TAMPA FL 33613 true Class A Common Stock 2019-06-04 4 M 0 40834 23.8 A 105136 D Class A Common Stock 2019-06-04 4 D 0 33816 28.74 D 71320 D Class B Common Stock 2416667 I See Footnote Class A Common Stock 125000 I See Footnote Class A Common Stock 5643 I See Footnote Stock Appreciation Rights 23.8 2019-06-04 4 M 0 40834 0 D 2019-06-07 Class A Common Stock 40834 0 D Membership Interests in Health Plan Intermediaries Holdings, 0 Class A Common Stock 0 2416667 I See Footnote Represents the exercise of stock appreciation rights prior to the expiration thereof. Shares retained by the issuer to satisfy the exercise price of stock appreciation rights exercised by the Reporting Person. Each share of Class B Common Stock held by the reporting persons, together with one Series B Membership Interest held by the reporting persons in Health Plan Intermediaries Holdings, LLC ("HPIH"), are together exchangeable, at any time, at the reporting persons' election, for one share of Class A Common Stock. This exchange right has no expiration date. This number of shares consists of 2,391,701 shares of Class B Common Stock held of record by Health Plan Intermediaries, LLC ("HPI") and 24,966 shares of Class B Common Stock held by Health Plan Intermediaries Sub, LLC ("HPIS"). Michael Kosloske is the sole member and primary manager of HPI, and has sole voting and dispositive power over the shares held by HPI. HPI is the sole managing member of HPIS and has sole voting and dispositive power over the shares held by HPIS. Mr. Kosloske, by virtue of his control of HPI and HPI's control of HPIS, may be deemed to beneficially own all the shares of Class B Common Stock held of record by each of HPI and HPIS. This number of shares consists of 123,750 shares of Class A Common Stock held of record by HPI and 1,250 shares of Class A Common Stock held by HPIS. Michael Kosloske is the sole member and primary manager of HPI, and has sole voting and dispositive power over the shares held by HPI. HPI is the sole managing member of HPIS and has sole voting and dispositive power over the shares held by HPIS. Mr. Kosloske, by virtue of his control of HPI and HPI's control of HPIS, may be deemed to beneficially own all the shares of Class A Common Stock held of record by each of HPI and HPIS. By Lori Kosloske. Michael Kosloske and Lori Kosloske are husband and wife. These stock-settled stock appreciation rights were granted to the Reporting Person under the Issuer's Long-Term Incentive Plan and, in accordance with the terms of the Long-Term Incentive Plan and an award agreement under the Long-Term Incentive Plan, vested in January 2018 upon the termination of the Reporting Person's employment with the Company. This number consists of 2,391,701 Class B Membership Interests in HPIH held of record by HPI and 24,966 interests held by HPIS. Michael Kosloske is the sole member and primary manager of HPI, and has sole voting and dispositive power over the interests held by HPI. HPI is the sole managing member of HPIS and has sole voting and dispositive power over the interests held by HPIS. Mr. Kosloske, by virtue of his control of HPI and HPI's control of HPIS, may be deemed to beneficially own all the Class B Membership Interests of HPIH held of record by each of HPI and HPIS. /s/ Michael W. Kosloske 2019-06-06