X0206 3 2018-06-08 0 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001742487 O'Meara Maeve C/O CASTLIGHT HEALTH, INC. 150 SPEAR ST., SUITE 400 SAN FRANCISCO CA 94105 0 1 0 0 EVP,Product&CustomerExperience Class B Common Stock 30881 D Employee Stock Option (right to buy) 0.79 2020-09-14 Class A Common Stock 30000 D Employee Stock Option (right to buy) 0.85 2021-10-11 Class A Common Stock 5000 D Employee Stock Option (right to buy) 1.09 2022-11-07 Class A Common Stock 9000 D Employee Stock Option (right to buy) 1.12 2023-02-11 Class A Common Stock 7500 D Employee Stock Option (right to buy) 2.35 2023-10-24 Class A Common Stock 20000 D Employee Stock Option (right to buy) 2.99 2026-02-23 Class B Common Stock 4424 D Employee Stock Option (right to buy) 2.99 2026-02-23 Class B Common Stock 150576 D Restricted Stock Units 0 Class B Common Stock 27000 D Restricted Stock Units 0 Class B Common Stock 21375 D Restricted Stock Units 0 Class B Common Stock 2188 D Restricted Stock Units 0 Class B Common Stock 93750 D Restricted Stock Units 0 Class B Common Stock 125000 D Restricted Stock Units 0 Class B Common Stock 34375 D Restricted Stock Units 0 Class B Common Stock 187500 D Restricted Stock Units 0 Class B Common Stock 100000 D The stock option has fully vested and is immediately exercisable. 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, 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. The stock option vested and continues to vest in 60 equal monthly installments beginning on March 24, 2016, until such time as the option is 100% vested, subject to the continuing service of the Reporting Person on each vesting date. 25% of the restricted stock units ("RSUs") vested on February 15, 2016 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting. 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 5 years as follows: 25% of the restricted stock units ("RSUs") vested on November 16, 2016. Thereafter, the shares vest in 12 quarterly installments each consisting of 5% of the shares subject to the RSU, and 1/12 of the remainder vests monthly thereafter until fully vested. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting. The RSUs vest over 5 years as follows: 25% of the RSUs vested on February 24, 2017. Thereafter, the shares vest in 12 quarterly installments each consisting of 5% of the shares subject to the RSU, and 1/12 of the remainder vests monthly thereafter until fully vested. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting. 25% of the RSUs vested on May 16, 2017 and the remainder will vest quarterly over two years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting. 100% of the RSUs will vest on May 16, 2020. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting. The RSUs vest over 5 years as follows: 25% of the RSUs vested on March 7, 2018. Thereafter, the shares vest in 12 quarterly installments each consisting of 5% of the shares subject to the RSU, and 1/12 of the remainder vests monthly thereafter until fully vested. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting. The RSUs vested and continue to vest in equal quarterly installments over four years, beginning on February 16, 2018. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting 100% of the RSUs will vest on December 31, 2018. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting. /s/ Jennifer Chaloemtiarana, by power of attorney 2018-06-13