X0206 3 2016-07-08 0 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001679464 Nolan Mangini Siobhan C/O CASTLIGHT HEALTH, INC. 150 SPEAR ST., SUITE 400 SAN FRANCISCO CA 94105 0 1 0 0 CFO & Treasurer Class B common stock 12713 D Employee Stock Option (right to buy) 1.08 2022-06-07 Class A common stock 10500 D Employee Stock Option (right to buy) 1.29 2023-07-23 Class A common stock 17500 D Employee Stock Option (right to buy) 2.35 2023-10-24 Class A common stock 20167 D Employee Stock Option (right to buy) 2.99 2026-02-23 Class A common stock 10000 D Restricted Stock Units 0 Class B common stock 5782 D Restricted Stock Units 0 Class B common stock 6875 D Restricted Stock Units 0 Class B common stock 30000 D Restricted Stock Units 0 Class B common stock 40000 D Restricted Stock Units 0 Class B common stock 30000 D 20% of the shares subject to the option vested on February 27, 2013. Thereafter, the shares vested or will vest in twelve installments each consisting of 1.667% of the shares subject to the option after the completion of each additional consecutive month of service, then with respect to the remaining shares, in 24 equal installments upon the completion of each additional consecutive month of service thereafter. 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. 20% of the shares subject to the option vested on June 1, 2014. Thereafter, the shares vested or will vest in twelve installments each consisting of 1.667% of the shares subject to the option after the completion of each additional consecutive month of service, then with respect to the remaining shares, in 24 equal installments upon the completion of each additional consecutive month of service thereafter. The stock option vested or will vest in 48 equal monthly installments beginning on October 23, 2014, until such time as the option is 100% vested, subject to the continuing employment of the Reporting Person on each vesting date. The stock option vested or will vest in 60 equal monthly installments beginning on March 24, 2016, until such time as the option is 100% vested, subject to the continuing employment of the Reporting Person on each vesting date. 25% of the restricted stock units ("RSUs") vested on November 17, 2015 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, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations. Each RSU represents a contingent right to receive 1 share of the Issuer's Class B common stock upon settlement for no consideration. 25% of the 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, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations. 25% of the RSUs will vest on August 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, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations. 25% of the RSUs will vest on November 16, 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, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations. 25% of the RSUs will vest on February 16, 2017 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, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations. /s/ Jennifer Chaloemtiarana, by power of attorney 2016-07-12