X0306 4 2017-08-10 0 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001601554 Colella Giovanni M. C/O CASTLIGHT HEALTH, INC. 150 SPEAR ST., SUITE 400 SAN FRANCISCO CA 94105 1 0 1 1 Executive Chairman Class B Common Stock 2017-08-10 4 C 0 10100 0 A 32320 I By living trust Class B Common Stock 2017-08-10 4 S 0 10100 3.8614 D 22220 I By living trust Class B Common Stock 2017-08-11 4 C 0 16700 0 A 38920 I By living trust Class B Common Stock 2017-08-11 4 S 0 16700 3.9127 D 22220 I By living trust Class B Common Stock 78906 D Class A Common Stock 0 2017-08-10 4 C 0 10100 0 D Class B Common Stock 10100 4677491 I By living trust Class A Common Stock 0 2017-08-11 4 C 0 16700 0 D Class B Common Stock 16700 4660791 I By living trust Class A Common Stock 0 Class B Common Stock 509638 509638 I By grantor retained annuity trust 1 Class A Common Stock 0 Class B Common Stock 160443 160443 I By grantor retained annuity trust 2 Class A Common Stock 0 Class B Common Stock 509638 509638 I By grantor retained annuity trust 3 Class A Common Stock 0 Class B Common Stock 160443 160443 I By grantor retained annuity trust 4 Reporting Person serves as a co-trustee. Represents the aggregate of sales effected on the same day at different prices. Represents the weighted average sales price per share. The shares sold at prices ranging from $3.85 to $3.875 per share. Full information regarding the number of shares sold at each price shall be provided upon request to the staff of the U.S. Securities and Exchange Commission, the Issuer, or a security holder of the Issuer. Represents the weighted average sales price per share. The shares sold at prices ranging from $3.85 to $3.975 per share. Full information regarding the number of shares sold at each price shall be provided upon request to the staff of the U.S. Securities and Exchange Commission, the Issuer, or a security holder of the Issuer. 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 serves as trustee and sole beneficiary. Reporting Person's spouse serves as trustee and sole beneficiary. /s/ Jennifer Chaloemtiarana, by power of attorney 2017-08-14