X0306 4 2014-03-19 0 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001199270 LAMONT ANN H C/O OAK INVESTMENT PARTNERS 3 PICKWICK PLAZA, SUITE 302 GREENWICH CT 06830 1 0 0 0 Series A Convertible Preferred Stock 0 2014-03-19 4 C 0 814884 0 D Class A Common Stock 814884 0 I See footnote Series A-1 Convertible Preferred Stock 0 2014-03-19 4 C 0 653582 0 D Class A Common Stock 653582 0 I See footnote Series B Convertible Preferred Stock 0 2014-03-19 4 C 0 8522522 0 D Class A Common Stock 8522522 0 I See footnote Series C Convertible Preferred Stock 0 2014-03-19 4 C 0 1459460 0 D Class A Common Stock 1459460 0 I See footnote Series D Convertible Preferred Stock 0 2014-03-19 4 C 0 345064 0 D Class A Common Stock 345064 0 I See footnote Class A Common Stock 0 2014-03-19 4 C 0 11795512 0 A Class B Common Stock 11795512 11917744 I See footnote In connection with the consummation of the Issuer's initial public offering (the "IPO") on March 19, 2014, each share of Convertible Preferred Stock automatically converted into one (1) share of Class A Common Stock for no additional consideration. All shares of Class A Common Stock issued upon conversion were aggregated. Each share of Class A Common Stock is convertible, at any time at the option of the holder, into one (1) share of Class B Common Stock. In addition, each share of Class A Common Stock will convert automatically into one (1) share of Class B Common Stock upon the transfer, whether or not for value, that occurs after the closing of the IPO to any transferee who is not a "Permitted Transferee", as defined in the Issuer's Restated Certificate of Incorporation in effect as of the date hereof. The shares of Class A Common Stock have no expiration date. Each share of the Issuer's Class A Common Stock will convert automatically into one (1) share of Class B Common Stock upon the earliest to occur of the following: (a) the first date on which the number of shares of Class A Common Stock then outstanding is less than 15,340,384 shares, (b) March 19, 2024, or (c) a time and date approved in writing by holders of at least a majority of the then-outstanding shares of Class A Common Stock. The shares of Class A Common Stock and Class B Common Stock have no expiration date. Represents securities directly owned by Oak Investment Partners XII, L.P and indirectly by Oak Associates XII, LLC, the sole general partner of Oak Investment Partners XII, L.P., and the Managing Members of Oak Associates XII, LLC. The "Managing Members" of Oak Associates XII, LLC are Ann H. Lamont, Bandel L. Carano, Edward F. Glassmeyer, Fredric W. Harman, Iftikar A. Ahmed, Grace A. Ames, Gerald R. Gallagher and Warren B. Riley. Such Managing Members have shared voting and investment control over all of the shares held by Oak Investment Partners XII, L.P. /s/ Ann H. Lamont 2014-03-19