X0206 3 2014-03-13 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 Class A Common Stock 0 Class B Common Stock 259721 D Series A Convertible Preferred Stock 0 Class A Common Stock 18517 D Series A-1 Convertible Preferred Stock 0 Class A Common Stock 7277 D Director Stock Option (right to buy) 0.06 2019-05-17 Class A Common Stock 76389 D Director Stock Option (right to buy) 16 2024-03-12 Class B Common Stock 35000 D Director Stock Option (right to buy) 16 2024-03-12 Class B Common Stock 25000 D Class A Common Stock 0 Class B Common Stock 1000 I Held by Nautilus Ventures LLC 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, pursuant to the Issuer's Restated Certificate of Incorporation (the "Post-Effective Certificate") that will be effective upon the consummation of the Issuer's initial public offering of its Class B Common Stock (the "IPO"), 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 Issuer's IPO to any transferee who is not a "Permitted Transferee", as defined in the Issuer's Post-Effective Certificate. The shares of Class A Common Stock have no expiration date. Pursuant to the Post-Effective Certificate, 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 falls below twenty percent of the number of shares of Class A common stock outstanding as of the closing of the IPO, (b) the ten year anniversary of the closing of the IPO, 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. Each share of Convertible Preferred Stock will be automatically converted into one (1) share of Class A Common Stock immediately prior to the consummation of the IPO, and has no expiration date. The stock option has fully vested and is immediately exercisable. The stock option vests in 12 equal monthly installments beginning one month after the vesting commencement date, until such time as the option is 100% vested, subject to the continuing service of the Reporting Person on each vesting 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 2014-03-13