X0306 4 2016-07-08 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 Nonstatutory Stock Option 4.01 2016-07-08 4 A 0 31250 A 2016-08-15 2026-07-07 Class B Common Stock 31250 56250 D Represents Stock Options. Options will vest and become exercisable over one year, in four equal quarterly installments, with the first such installment to vest on August 15, 2016. Includes 31,250 Stock Options 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. Not applicable 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 2016-07-12 Oak Investment Partners XII, LP 2016-07-12