X0306 4 2014-03-19 0 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001601541 Michel Christopher P. C/O CASTLIGHT HEALTH, INC. TWO RINCON CTR., 121 SPEAR ST., STE. 300 SAN FRANCISCO CA 94105 1 0 0 0 Series A Convertible Preferred Stock 0 2014-03-19 4 C 0 18517 0 D Class A Common Stock 18517 0 D Series A-1 Convertible Preferred Stock 0 2014-03-19 4 C 0 7277 0 D Class A Common Stock 7277 0 D Class A Common Stock 0 2014-03-19 4 C 0 25794 0 A Class B Common Stock 25794 285515 D Class A Common Stock 0 Class B Common Stock 1000 1000 I Held by Nautilus Ventures LLC 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. Reporting Person is the Managing Director of Nautilus Ventures LLC, and as such, shares voting and dispositive power over the shares held by Nautilus Ventures LLC. Reporting Person disclaims beneficial ownership of these shares (except to the extent of his pecuniary interest therein), and the inclusion of these shares in this report shall not be deemed an admission by the Reporting Person of beneficial ownership of all of the reported shares for the purposes of Section 16 or for any other purpose. /s/ Charles Ott, by power of attorney 2014-03-19