X0306 4 2017-08-15 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 2017-08-15 4 M 0 9187 0 A 88093 D Class B Common Stock 2017-08-16 4 S 0 3662 3.9027 D 84431 D Class B Common Stock 2017-08-16 5 J 0 5525 0 D 78906 D Class B Common Stock 2017-08-16 5 J 0 5525 0 A 27745 I By living trust Class B Common Stock 2017-08-16 4 C 0 26400 0 A 54145 I By living trust Class B Common Stock 2017-08-16 4 S 0 26400 3.911 D 27745 I By living trust Restricted Stock Units 0 2017-08-15 4 M 0 9187 0 D Class B Common Stock 9187 64313 D Class A Common Stock 0 2017-08-16 4 C 0 26400 0 D Class B Common Stock 26400 4610591 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 106443 106443 I By grantor retained annuity trust 4 Release and settlement of restricted stock units ("RSUs") granted to the Reporting Person on June 17, 2015, the grant of which was previously reported by the Reporting Person on a Form 4. Represents the aggregate of sales effected on the same day at different prices. All of these shares were sold to cover taxes and fees due upon the release and settlement of the RSUs. Represents the weighted average sales price per share. The shares sold at prices ranging from $3.85 to $3.95 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. Re-registration of shares in the name of the Reporting Person's living trust, effecting only a change in the form of beneficial ownership. Reporting Person serves as a co-trustee. Represents the weighted average sales price per share. The shares sold at prices ranging from $3.85 to $4.05 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 RSU represents a contingent right to receive 1 share of the Issuer's Class B common stock upon settlement for no consideration. The RSUs vest over 4 years as follows: 25% of the RSUs vested on May 15, 2016 and the remainder will vest on each quarterly anniversary thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting. 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 2017-08-17