Ownership Submission
FORM 4
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940
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(Print or Type Responses)
1. Name and Address of Reporting Person *
LAMONT ANN H
  2. Issuer Name and Ticker or Trading Symbol
CASTLIGHT HEALTH, INC. [CSLT]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
__X__ Director _____ 10% Owner
_____ Officer (give title below) _____ Other (specify below)
(Last)
(First)
(Middle)
C/O OAK INVESTMENT PARTNERS, 3 PICKWICK PLAZA, SUITE 302
3. Date of Earliest Transaction (Month/Day/Year)
03/19/2014
(Street)

GREENWICH, CT 06830
4. If Amendment, Date Original Filed(Month/Day/Year)
6. Individual or Joint/Group Filing(Check Applicable Line)
_X_ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person
(City)
(State)
(Zip)
Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 3. Transaction Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I)
(Instr. 4)
7. Nature of Indirect Beneficial Ownership
(Instr. 4)
Code V Amount (A) or (D) Price

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Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year) 3A. Deemed Execution Date, if any (Month/Day/Year) 4. Transaction Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4, and 5)
6. Date Exercisable and Expiration Date
(Month/Day/Year)
7. Title and Amount of Underlying Securities
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 4)
10. Ownership Form of Derivative Security: Direct (D) or Indirect (I)
(Instr. 4)
11. Nature of Indirect Beneficial Ownership
(Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Series A Convertible Preferred Stock $ 0 (1) 03/19/2014   C     814,884   (1)   (1) Class A Common Stock (2) (3) 814,884 $ 0 0 I See footnote (4)
Series A-1 Convertible Preferred Stock $ 0 (1) 03/19/2014   C     653,582   (1)   (1) Class A Common Stock (2) (3) 653,582 $ 0 0 I See footnote (4)
Series B Convertible Preferred Stock $ 0 (1) 03/19/2014   C     8,522,522   (1)   (1) Class A Common Stock (2) (3) 8,522,522 $ 0 0 I See footnote (4)
Series C Convertible Preferred Stock $ 0 (1) 03/19/2014   C     1,459,460   (1)   (1) Class A Common Stock (2) (3) 1,459,460 $ 0 0 I See footnote (4)
Series D Convertible Preferred Stock $ 0 (1) 03/19/2014   C     345,064   (1)   (1) Class A Common Stock (2) (3) 345,064 $ 0 0 I See footnote (4)
Class A Common Stock $ 0 (2) (3) 03/19/2014   C   11,795,512 (1)     (2)(3)   (2)(3) Class B Common Stock (3) 11,795,512 $ 0 11,917,744 I See footnote (4)

Reporting Owners

Reporting Owner Name / Address Relationships
 Director  10% Owner  Officer  Other
LAMONT ANN H
C/O OAK INVESTMENT PARTNERS
3 PICKWICK PLAZA, SUITE 302
GREENWICH, CT 06830
  X      

Signatures

 /s/ Ann H. Lamont   03/19/2014
**Signature of Reporting Person Date

Explanation of Responses:

* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
(1) In connection with the consummation of the Issuer's initial public offering (the "IPO") on March 19, 2014, each share of Convertible Preferred Stock automatically converted into one (1) share of Class A Common Stock for no additional consideration. All shares of Class A Common Stock issued upon conversion were aggregated.
(2) 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.
(3) 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.
(4) Represents securities directly owned by Oak Investment Partners XII, L.P and indirectly by Oak Associates XII, LLC, the sole general partner of Oak Investment Partners XII, L.P., and the Managing Members of Oak Associates XII, LLC. The "Managing Members" of Oak Associates XII, LLC are Ann H. Lamont, Bandel L. Carano, Edward F. Glassmeyer, Fredric W. Harman, Iftikar A. Ahmed, Grace A. Ames, Gerald R. Gallagher and Warren B. Riley. Such Managing Members have shared voting and investment control over all of the shares held by Oak Investment Partners XII, L.P.

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