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
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                      	Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934 or Section 30(h) of the Investment Company Act of 1940	                      	

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 STREET, SUITE 400	3. Date of Earliest Transaction (MM/DD/YYYY)

11/16/2020		
(Street)

SAN FRANCISCO, CA 94105
(City)       (State)       (Zip)	4. If Amendment, Date Original Filed (MM/DD/YYYY)

 	6. Individual or Joint/Group Filing (Check Applicable Line)

_X _ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person	

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned	
1.Title of Security
(Instr. 3)	2. Trans. Date	2A. Deemed Execution Date, if any	3. Trans. 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	  	1875 (1)	A	$0.00 	129784 (2)	D 	 	
Class B Common Stock 	11/16/2020 	 	M	  	3750 (1)	A	$0.00 	133534 	D 	 	
Class B Common Stock 	11/16/2020 	 	M	  	3750 (1)	A	$0.00 	137284 	D 	 	
Class B Common Stock 	11/16/2020 	 	M	  	9375 (1)	A	$0.00 	146659 	D 	 	
Class B Common Stock 	11/16/2020 	 	M	  	8437 (1)	A	$0.00 	155096 	D 	 	
Class B Common Stock 	11/16/2020 	 	M	  	52817 (1)	A	$0.00 	207913 	D 	 	
Class B Common Stock 	11/16/2020 	 	M	  	56250 (1)	A	$0.00 	264163 	D 	 	
Class B Common Stock 	11/17/2020 	 	S(3)	  	48844 	D	$1.1391 (4)	215319 	D 	 	

Table II - Derivative Securities Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)	
1. Title of Derivate Security
(Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Trans. Date	3A. Deemed Execution Date, if any	4. Trans. 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	7. Title and Amount of Securities Underlying Derivative Security
(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 	  	  	1875  	 (6)	 (6)	Class B Common Stock 	1875 	$0.00 	1250 	D 	 	
Restricted Stock Units (RSU) 	 (5)	11/16/2020 	 	M 	  	  	3750  	 (7)	 (7)	Class B Common Stock 	3750 	$0.00 	3750 	D 	 	
Restricted Stock Units (RSU) 	 (5)	11/16/2020 	 	M 	  	  	3750  	 (8)	 (8)	Class B Common Stock 	3750 	$0.00 	8750 	D 	 	
Restricted Stock Units (RSU) 	 (5)	11/16/2020 	 	M 	  	  	9375  	 (8)	 (8)	Class B Common Stock 	9375 	$0.00 	21875 	D 	 	
Restricted Stock Units (RSU) 	 (5)	11/16/2020 	 	M 	  	  	8437  	 (9)	 (9)	Class B Common Stock 	8437 	$0.00 	25313 	D 	 	
Restricted Stock Units (RSU) 	 (5)	11/16/2020 	 	M 	  	  	52817  	 (10)	 (10)	Class B Common Stock 	52817 	$0.00 	211269 	D 	 	
Restricted Stock Units (RSU) 	 (5)	11/16/2020 	 	M 	  	  	56250  	 (11)	 (11)	Class B Common Stock 	56250 	$0.00 	243750 	D 	 	

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) 	Includes 1,770 shares of Class B Common Stock acquired under the Issuer's employee stock purchase plan on August 31, 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 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) 	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. The underlying vested shares settled on November 16, 2020.	
(7) 	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. The underlying vested shares settled on November 16, 2020.	
(8) 	1/16th of the RSUs vested on November 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 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.	
(10) 	1/16th of the RSUs vested on February 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.	
(11) 	1/16th of the RSUs vest 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.	

Reporting Owners	
Reporting Owner Name / Address	Relationships	
	Director	10% Owner	Officer	Other	
Bondurant William
C/O CASTLIGHT HEALTH, INC.
150 SPEAR STREET, SUITE 400
SAN FRANCISCO, CA 94105			Chief Financial Officer		

Signatures		
/s/ Mary Ahern, by power of attorney		11/18/2020	
**Signature of Reporting Person		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).	
Note:	File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.	
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.	

POWER OF ATTORNEY
KNOW ALL MEN BY THESE PRESENTS, that the undersigned hereby constitutes and appoints Alex Shvartsman and Mary Ahern as his true and lawful attorney-in-fact to:
(1) execute for and on behalf of the undersigned, in the undersigned's capacity as a representative of Castlight Health, Inc. (the "Company"), any and all Form ID, or Form 3, 4 or 5 reports and any amendments thereto required to be filed by the undersigned in accordance with Section 16(a) of the Securities Exchange Act of 1934 (the "Exchange Act") and the rules thereunder with respect to transactions in the Company's securities;
(2) do and perform any and all acts for and on behalf of the undersigned which may be necessary or desirable to complete and execute any such Form ID, or Form 3, 4 or 5 report and any amendments thereto and timely file such report with the U.S. Securities and Exchange Commission and any stock exchange or similar authority; and
(3) take any other action of any type whatsoever in connection with the foregoing which, in the opinion of such attorney in-fact, may be of benefit to, in the best interest of, or legally required by, the undersigned, it being understood that the documents executed by such attorney in-fact on behalf of the undersigned, pursuant to this Power of Attorney, shall be in such form and shall contain such terms and conditions as such attorney in-fact may approve in his or her discretion.
The undersigned hereby grants to such attorney-in-fact full power and authority to do and perform each and every act and thing whatsoever requisite, necessary, and proper to be done in the exercise of any of the rights and powers herein granted, as fully to all intents and purposes as the undersigned might or could do if personally present, with full power of substitution or revocation, hereby ratifying and confirming all that such attorney-in-fact, or her/his substitute or substitutes, shall lawfully do or cause to be done by virtue of this Power of Attorney and the rights and powers herein granted. The undersigned acknowledges that no such attorney in-fact, in serving in such capacity at the request of the undersigned, is hereby assuming, nor is the Company hereby assuming, any of the undersigned's responsibilities to comply with Section 16 of the Exchange Act.
This Power of Attorney shall remain in full force and effect until the undersigned is no longer required to file Form 3, 4 or 5 reports with respect to the undersigned's holdings of and transactions in securities issued by the Company, unless earlier revoked by the undersigned in a signed writing delivered to the foregoing attorney in-fact.
IN WITNESS WHEREOF, the undersigned has caused this Power of Attorney to be executed as of November 16, 2020.

/s/ Will Bondurant
Will Bondurant