Sec Form 3 Filing - Bondurant William @ CASTLIGHT HEALTH, INC. - 2019-11-15

FORM 3 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 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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1. Name and Address of Reporting Person Bondurant William 2. Issuer Name and Ticker or Trading Symbol CASTLIGHT HEALTH, INC. [ CSLT] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director _____ 10% Owner X __ Officer (give title below) _____ Other (specify below) Chief Financial Officer (Last) (First) (Middle) C/O CASTLIGHT HEALTH, INC., 150 SPEAR ST., SUITE 400 3. Date of Earliest Transaction (MM/DD/YY) 11/15/2019 (Street) SAN FRANCISCO, CA94105 4. If Amendment, Date Original Filed (MM/DD/YY) 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 (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 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 Class B Common Stock 63,996 D

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 (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 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 (MM/DD/YY) 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 Employee Stock Option (right to buy) $ 1.29 ( 1 ) 07/23/2023 Class A Common Stock ( 2 ) 1,750 D Employee Stock Option (right to buy) $ 2.35 ( 1 ) 10/24/2023 Class A Common Stock ( 2 ) 5,757 D Employee Stock Option (right to buy) $ 2.99 ( 3 ) 02/23/2026 Class B Common Stock 7,500 D Employee Stock Option (right to buy) $ 2.99 ( 4 ) 02/23/2026 Class B Common Stock 12,000 D Employee Stock Option (right to buy) $ 2.99 ( 3 ) 02/23/2026 Class B Common Stock 6,000 D Employee Stock Option (right to buy) $ 3.22 ( 5 ) 02/13/2029 Class B Common Stock 10,000 D Restricted Stock Units (RSU) ( 7 ) ( 6 ) ( 6 ) Class B Common Stock 4,375 D Restricted Stock Units (RSU) ( 7 ) ( 8 ) ( 8 ) Class B Common Stock 10,000 D Restricted Stock Units (RSU) ( 7 ) ( 9 ) ( 9 ) Class B Common Stock 37,500 D Restricted Stock Units (RSU) ( 7 ) ( 9 ) ( 9 ) Class B Common Stock 15,000 D Restricted Stock Units (RSU) ( 7 ) ( 10 ) ( 10 ) Class B Common Stock 39,375 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other Bondurant William C/O CASTLIGHT HEALTH, INC. 150 SPEAR ST., SUITE 400 SAN FRANCISCO, CA94105 Chief Financial Officer Signatures /s/ William Bondurant, by Trevor Dutcher, Attorney-in-Fact 11/18/2019 Signature of Reporting Person Date

Explanation of Responses:

( 1 )The stock option has fully vested and is immediately exercisable. ( 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 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, (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, and (d) 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 sha res of Class A Common Stock have no expiration date ( 3 )The stock option vested and continues to vest in 60 equal monthly installments beginning on February 24, 2016, until such time as the option is 100% vested, subject to the continuing service of the Reporting Person on each vesting date. ( 4 )The stock option vested and continues to vest in 48 equal monthly installments beginning on February 24, 2016, until such time as the option is 100% vested, subject to the continuing service of the Reporting Person on each vesting date. ( 5 )The stock option vested and continues to vest in 12 equal quarterly installments over three years, with the first vesting date being May 16, 2019, until such time as the option is 100% vested, subject to the continuing service of the Reporting Person on each vesting date. ( 6 )1/4th of the RSUs vested on May 16, 2018, and the remainder will vest 1/16th quarterly over three years in equal installments, subject to the continuing service of the Reporting Person on each vesting date. ( 7 )Each RSU represents a contingent right to receive one (1) share of the Class B Common Stock upon settlement for no consideration. ( 8 )1/4th of the RSUs vested on August 16, 2018, and the remainder will vest 1/16th quarterly over three years in equal installments, subject to the continuing service of the Reporting Person on each vesting date. ( 9 )1/16th of the RSUs vested on November 16, 2018, and the remainder will vest 1/16th quarterly thereafter in equal installments, subject to the continuing service of the Reporting Person on each vesting date. ( 10 )1/16th of the RSUs vested on May 16, 2019, and the remainder will vest 1/16th quarterly thereafter in equal installments, subject to the continuing service of the Reporting Person on each vesting date.

Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.

* 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).

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