X0306 4 2019-11-29 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 2019-11-29 4 S 0 298974 18.2987 D 69655 I See Footnote Class A Common Stock 2019-11-29 4 S 0 10576 19.2641 D 59079 I See Footnote Class A Common Stock 2019-12-02 4 S 0 52829 18.3732 D 6250 I See Footnote Class A Common Stock 5643 I See Footnote Class B Common Stock 1916667 I See Footnote Represents the weighted average of a range of sale prices from $18.00 to $18.99. The reporting person undertakes to provide to the Staff of the Securities and Exchange Commission, the Company or any stockholder of the Company, upon request, full information regarding the number of shares sold at each separate price. This number of shares consists of shares of Class A Common Stock held of record by Health Plan Intermediaries, LLC ("HPI") and Health Plan Intermediaries Sub, LLC ("HPIS"). HPIS owns 6,250 of such shares and the remainder are held by HPI. 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. Represents the weighted average of a range of sale prices from $19.00 to $19.66. The reporting person undertakes to provide to the Staff of the Securities and Exchange Commission, the Company or any stockholder of the Company, upon request, full information regarding the number of shares sold at each separate price. Represents the weighted average of a range of sale prices from $18.00 to $18.80. The reporting person undertakes to provide to the Staff of the Securities and Exchange Commission, the Company or any stockholder of the Company, upon request, full information regarding the number of shares sold at each separate price. By Lori Kosloske. Michael Kosloske and Lori Kosloske are husband and wife. 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 1,896,701 shares of Class B Common Stock held of record by HPI and 19,966 shares of Class B 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 B Common Stock held of record by each of HPI and HPIS. /s/ Michael W. Kosloske 2019-12-03