X0206 3 2014-03-13 0 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001410698 Womack Randall J. C/O CASTLIGHT HEALTH, INC. TWO RINCON CTR., 121 SPEAR ST., STE. 300 SAN FRANCISCO CA 94105 0 1 1 0 COO and V.P. Class A Common Stock 0 Class B Common Stock 3333 D Series A Convertible Preferred Stock 0 Class A Common Stock 22220 D Series A-1 Convertible Preferred Stock 0 Class A Common Stock 8732 D Series C Convertible Preferred Stock 0 Class A Common Stock 46920 D Employee Stock Option (right to buy) 0.79 2020-11-08 Class A Common Stock 158108 D Employee Stock Option (right to buy) 0.79 2020-11-08 Class A Common Stock 1264864 D Employee Stock Option (right to buy) 1.12 2023-02-11 Class A Common Stock 230000 D Employee Stock Option (right to buy) 16 2024-03-12 Class B Common Stock 120000 D 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. 25% of the shares subject to the option vests on the one-year anniversary of the vesting commencement date, and thereafter vests as to 1/48th of the shares in equal monthly installments. The shares subject to the stock option vests in 24 equal monthly installments, subject to the Reporting Person's completion of each consecutive month of continuous service following the second anniversary of the vesting commencement. The stock option vests in 48 equal monthly installments beginning one month after the vesting commencement date, until such time as the option is 100% vested, subject to the continuing employment of the Reporting Person on each vesting date. /s/ Charles Ott, by power of attorney 2014-03-13