Sec Form 4 Filing - O'Meara Maeve @ CASTLIGHT HEALTH, INC. - 2020-11-16

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 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 O'Meara Maeve 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 X __ Officer (give title below) _____ Other (specify below) Chief Executive Officer (Last) (First) (Middle) C/O CASTLIGHT HEALTH, INC., 150 SPEAR STREET, SUITE 400 3. Date of Earliest Transaction (MM/DD/YY) 11/16/2020 (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 11/16/2020 M 125,000 ( 1 ) A $ 0 643,453 D Class B Common Stock 11/16/2020 M 9,375 ( 1 ) A $ 0 652,828 D Class B Common Stock 11/16/2020 M 37,500 ( 1 ) A $ 0 690,328 D Class B Common Stock 11/16/2020 M 37,500 ( 1 ) A $ 0 727,828 D Class B Common Stock 11/16/2020 M 69,187 ( 1 ) A $ 0 797,015 D Class B Common Stock 11/16/2020 M 129,310 ( 1 ) A $ 0 926,325 D Class B Common Stock 11/16/2020 M 186,000 ( 1 ) A $ 0 1 ,112,325 D Class B Common Stock 11/16/2020 M 689,656 ( 2 ) A $ 0 1,801,981 D Class B Common Stock 11/17/2020 S( 3 ) 577,907 D $ 1.1439 ( 4 ) 1,224,074 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 Restricted Stock Units (RSU) ( 5 ) 11/16/2020 M 125,000 ( 6 ) ( 6 ) Class B Common Stock 125,000 $ 0 0 D Restricted Stock Units (RSU) ( 5 ) 11/16/2020 M 9,375 ( 7 ) ( 7 ) Class B Common Stock 9,375 $ 0 3,125 D Restricted Stock Units (RSU) ( 5 ) 11/16/2020 M 37,500 ( 8 ) ( 8 ) Class B Common Stock 37,500 $ 0 62,500 D Restricted Stock Units (RSU) ( 5 ) 11/16/2020 M 37,500 ( 9 ) ( 9 ) Class B Common Stock 37,500 $ 0 75,000 D Restricted Stock Units (RSU) ( 5 ) 11/16/2020 M 69,187 ( 10 ) ( 10 ) Class B Common Stock 69,187 $ 0 207,563 D Restricted Stock Units (RSU) ( 5 ) 11/16/2020 M 129,310 ( 11 ) ( 11 ) Class B Common Stock 129,310 $ 0 474,139 D Restricted Stock Units (RSU) ( 5 ) 11/16/2020 M 186,000 ( 12 ) ( 12 ) Class B Common Stock 186,000 $ 0 806,000 D Restricted Stock Units (RSU) ( 5 ) 11/16/2020 M 689,656 ( 13 ) 08/16/2021 Class B Common Stock 689,656 $ 0 0 D

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other O'Meara Maeve C/O CASTLIGHT HEALTH, INC. 150 SPEAR STREET, SUITE 400 SAN FRANCISCO, CA94105 X Chief Executive Officer Signatures /s/ Mary Ahern, by power of attorney 11/18/2020 Signature of Reporting Person Date

Explanation of Responses:

( 1 )On November 16, 2020, these shares of Class B Common Stock were issued in settlement of the RSUs that vested on each of May 16, 2020, August 16, 2020 and November 16, 2020. Delivery of the shares in settlement of the RSUs that vested on May 16, 2020 and August 16, 2020 was deferred to November 16, 2020. ( 2 )On November 16, 2020, these shares of Class B Common Stock were issued in settlement of the RSUs that vested on August 17, 2020. Delivery of the shares in settlement of the vested RSUs was deferred to November 16, 2020. ( 3 )Represents the aggregate number of shares sold by the Reporting Person to cover taxes and fees due upon the release and settlement of the RSUs. The Reporting Person did not sell or otherwise dispose of any of the shares reported on this Form 4 for any reason other than to cover required taxes and fees. ( 4 )Represents the weighted average sales price per share. The shares sold at prices ranging from $1.13 to $1.17 per share. Full information regarding the number of shares sold at each price shall be provided upon request to the staff of the U.S. Securities and Exchange Commission, the Issuer, or a security holder of the Issuer. ( 5 )Each RSU represents a contingent right to receive one (1) share of the Class B Common Stock upon settlement for no consideration. ( 6 )100% of the RSUs vested on May 16, 2020. The underlying vested shares settled on November 16, 2020. ( 7 )1/4th of the RSUs vested on March 7, 2018, and the remainder will vest 1/20th quarterly in 12 equal installments and then 1/12th monthly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. The underlying vested shares settled on November 16, 2020. ( 8 )1/16th of the RSUs vested on February 16, 2018, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. The underlying vested shares settled on November 16, 2020. ( 9 )1/16th of the RSUs vested on August 16, 2018, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. The underlying vested shares settled on November 16, 2020. ( 10 )1/16th of the RSUs vested on May 16, 2019, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. The underlying vested shares settled on November 16, 2020. ( 11 )1/16th of the RSUs vested on November 16, 2019, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. The underlying vested shares settled on November 16, 2020. ( 12 )1/16th of the RSUs vested on May 16, 2020, and the remainder will vest 1/16th quarterly in equal installments, subject to the continuing service of the Reporting Person on each vesting date. The underlying vested shares settled on November 16, 2020. ( 13 )The RSU vested on August 17, 2020. The underlying vested shares settled on November 16, 2020.

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