FORM 3
        	UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

INITIAL STATEMENT OF 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. Date of Event Requiring Statement (MM/DD/YYYY)
11/15/2019 
	3. Issuer Name and Ticker or Trading Symbol

CASTLIGHT HEALTH, INC. [CSLT]	
(Last)       (First)       (Middle)

C/O CASTLIGHT HEALTH, INC., 150 SPEAR ST., SUITE 400	4. Relationship of Reporting Person(s) to Issuer (Check all applicable)

_____ Director                          _____ 10% Owner
___X___ Officer (give title below)        _____ Other (specify below)
Chief Financial Officer /	
(Street)

SAN FRANCISCO, CA 94105      

(City)             (State)             (Zip)	5. 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 Beneficially Owned	
1.Title of Security
(Instr. 4)	2. Amount of Securities Beneficially Owned
(Instr. 4)	3. Ownership Form: Direct (D) or Indirect (I)
(Instr. 5)	4. Nature of Indirect Beneficial Ownership
(Instr. 5)	
Class B Common Stock 	63996 	D 	 	

Table II - Derivative Securities Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)	
1. Title of Derivate Security
(Instr. 4)	2. Date Exercisable and Expiration Date
(MM/DD/YYYY)	3. Title and Amount of Securities Underlying Derivative Security
(Instr. 4)	4. Conversion or Exercise Price of Derivative Security	5. Ownership Form of Derivative Security: Direct (D) or Indirect (I)
(Instr. 5)	6. Nature of Indirect Beneficial Ownership
(Instr. 5)	
	Date Exercisable	Expiration Date	Title	Amount or Number of Shares				
Employee Stock Option (right to buy) 	 (1)	7/23/2023 	Class A Common Stock (2)	1750 	$1.29 	D 	 	
Employee Stock Option (right to buy) 	 (1)	10/24/2023 	Class A Common Stock (2)	5757 	$2.35 	D 	 	
Employee Stock Option (right to buy) 	 (3)	2/23/2026 	Class B Common Stock 	7500 	$2.99 	D 	 	
Employee Stock Option (right to buy) 	 (4)	2/23/2026 	Class B Common Stock 	12000 	$2.99 	D 	 	
Employee Stock Option (right to buy) 	 (3)	2/23/2026 	Class B Common Stock 	6000 	$2.99 	D 	 	
Employee Stock Option (right to buy) 	 (5)	2/13/2029 	Class B Common Stock 	10000 	$3.22 	D 	 	
Restricted Stock Units (RSU) 	 (6)	 (6)	Class B Common Stock 	4375 	 (7)	D 	 	
Restricted Stock Units (RSU) 	 (8)	 (8)	Class B Common Stock 	10000 	 (7)	D 	 	
Restricted Stock Units (RSU) 	 (9)	 (9)	Class B Common Stock 	37500 	 (7)	D 	 	
Restricted Stock Units (RSU) 	 (9)	 (9)	Class B Common Stock 	15000 	 (7)	D 	 	
Restricted Stock Units (RSU) 	 (10)	 (10)	Class B Common Stock 	39375 	 (7)	D 	 	

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 shares 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.	

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, CA 94105			Chief Financial Officer		

Signatures		
/s/ William Bondurant, by Trevor Dutcher, Attorney-in-Fact		11/18/2019	
**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 5(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 Trevor Dutcher, and each of them, 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 each 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 his or her 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 attorneys‑in-fact.
IN WITNESS WHEREOF, the undersigned has caused this Power of Attorney to be executed as of this 16 day of October 2019.

/s/ William Bondurant

 
William Bondurant