X0306 4 2015-06-17 0001433714 CASTLIGHT HEALTH, INC. CSLT 0001199270 LAMONT ANN H C/O OAK INVESTMENT PARTNERS 901 MAIN AVENUE, SUITE 600 NORWALK CT 06851 1 0 1 0 0001365607 OAK INVESTMENT PARTNERS XII L P C/O OAK INVESTMENT PARTNERS 901 MAIN AVENUE, SUITE 600 NORWALK CT 06851 0 0 1 0 Class B Common Stock 2015-06-17 4 A 0 12500 0 A 12500 I See Class A Common Stock 11917744 I See Represents an award of restricted stock units ("RSUs"). 25% of the RSUs will vest on August 15, 2015 and an additional 25% will vest on each quarterly anniversary thereafter. Each RSU represents a contingent right to receive one share of the Issuer's Class B Common Stock upon settlement for no consideration. Includes 12,500 RSUs which are held by Ann H. Lamont on behalf of Oak Investment Partners XII, Limited Partnership ("Oak XII"). Ms. Lamont is a Managing Member of Oak Associates XII, L.L.C., the General Partner of Oak XII. Includes 11,917,744 shares of Class A Common Stock beneficially owned by Oak XII. Ann H. Lamont is a Director of the Issuer. This Form 4 is being filed by Ann H. Lamont and Oak XII, collectively the "Reporting Persons". Each Reporting Person disclaims the existence of a "group" and disclaims beneficial ownership of any securities (except to the extent of such Reporting Person's pecuniary interest in such securities) other than any securities reported herein as being directly owned by such Reporting Person, and this report shall not be deemed an admission that such Reporting Person is the beneficial owner of any such securities for purposes of Section 16 or for any other purpose. Ann H. Lamont 2015-06-19 Oak Investment Partners XII, LP 2015-06-19