UNITED STATES 
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
 
SCHEDULE 13D
(Rule 13d-101)
 
INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT
TO § 240.13d-1(a) AND AMENDMENTS THERETO FILED PURSUANT TO
§ 240.13d-2(a)
 
(Amendment No. )1
 
Castlight Health, Inc.
(Name of Issuer)
 
Class B Common Stock, par value $0.0001
(Title of Class of Securities)
 
14862Q 10 0
(CUSIP Number)
 
STEVE WOLOSKY, ESQ.
OLSHAN FROME WOLOSKY LLP
1325 Avenue of the Americas
New York, New York 10019
(212) 451-23007
(Name, Address and Telephone Number of Person
Authorized to Receive Notices and Communications)
 
March 27, 2020
(Date of Event Which Requires Filing of This Statement)
 
If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§ 240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box ☒.
 
Note: Schedules filed in paper format shall include a signed original and five copies of the schedule, including all exhibits. See § 240.13d-7 for other parties to whom copies are to be sent.
 
_______________
 
1       The remainder of this cover page shall be filled out for a reporting person’s initial filing on this form with respect to the subject class of securities, and for any subsequent amendment containing information which would alter disclosures provided in a prior cover page.
 
The information required on the remainder of this cover page shall not be deemed to be “filed” for the purpose of Section 18 of the Securities Exchange Act of 1934 (“Act”) or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).

CUSIP No. 14862Q 10 0

 	1	 	NAME OF REPORTING PERSONS	 	
 	 	 	 	 	
 	 	 	 	Raging Capital Management, LLC	 	
 	2	 	CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP*	(a) ☐	
 	 	 	 	(b) ☐	
 	 	 	 	 	 	
 	3	 	SEC USE ONLY	 	 	

 	4	 	SOURCE OF FUNDS	 	
 	 	 	 	 	
 	 	 	 	AF	 	
 	5	 	CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEM 2(d) OR 2(e)	    ☐	

 	6	 	CITIZENSHIP OR PLACE OF ORGANIZATION	 	
 	 	 	 	 	
 	 	 	 	DELAWARE	 	
NUMBER OF	 	7	 	SOLE VOTING POWER	 	
SHARES	 	 	 	 	 	
BENEFICIALLY	 	 	 	 	- 0 -	 	
OWNED BY	 	8	 	SHARED VOTING POWER	 	
EACH	 	 	 	 	 	
REPORTING	 	 	 	 	10,423,517	 	
PERSON WITH	 	9	 	SOLE DISPOSITIVE POWER	 	
	 	 	 	 	 	
 	 	 	 	 	- 0 -	 	
 	 	10	 	SHARED DISPOSITIVE POWER	 	
 	 	 	 	 	 	
 	 	 	 	 	10,423,517	 	
 	11	 	AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON	 	
 	 	 	 	 	
 	 	 	 	10,423,517	 	
 	12	 	CHECK BOX IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES	    ☐	

 	13	 	PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)	 	
 	 	 	 	 	
 	 	 	 	9.1%	 	
 	14	 	TYPE OF REPORTING PERSON	 	
 	 	 	 	 	
 	 	 	 	IA	 	

2
CUSIP No. 14862Q 10 0

 	1	 	NAME OF REPORTING PERSONS	 	
 	 	 	 	 	
 	 	 	 	William C. Martin	 	
 	2	 	CHECK THE APPROPRIATE BOX IF A MEMBER OF A GROUP*	(a) ☐	
 	 	 	 	(b) ☐	
 	 	 	 	 	 	
 	3	 	SEC USE ONLY	 	 	

 	4	 	SOURCE OF FUNDS	 	
 	 	 	 	 	
 	 	 	 	AF	 	
 	5	 	CHECK BOX IF DISCLOSURE OF LEGAL PROCEEDINGS IS REQUIRED PURSUANT TO ITEM 2(d) OR 2(e)	    ☐	

 	6	 	CITIZENSHIP OR PLACE OF ORGANIZATION	 	
 	 	 	 	 	
 	 	 	 	USA	 	
NUMBER OF	 	7	 	SOLE VOTING POWER	 	
SHARES	 	 	 	 	 	
BENEFICIALLY	 	 	 	 	- 0 -	 	
OWNED BY	 	8	 	SHARED VOTING POWER	 	
EACH	 	 	 	 	 	
REPORTING	 	 	 	 	10,423,517	 	
PERSON WITH	 	9	 	SOLE DISPOSITIVE POWER	 	
	 	 	 	 	 	
 	 	 	 	 	- 0 -	 	
 	 	10	 	SHARED DISPOSITIVE POWER	 	
 	 	 	 	 	 	
 	 	 	 	 	10,423,517	 	
 	11	 	AGGREGATE AMOUNT BENEFICIALLY OWNED BY EACH REPORTING PERSON	 	
 	 	 	 	 	
 	 	 	 	10,423,517	 	
 	12	 	CHECK BOX IF THE AGGREGATE AMOUNT IN ROW (11) EXCLUDES CERTAIN SHARES	    ☐	
 	 	 		 	
 	 	 	 	9.1%	 	
 	13	 	PERCENT OF CLASS REPRESENTED BY AMOUNT IN ROW (11)	 	

 	14	 	TYPE OF REPORTING PERSON	 	
 	 	 	 	 	
 	 	 	 	HC	 	

3
CUSIP No. 14862Q 10 0
 
The following constitutes the Schedule 13D filed by the undersigned (the “Schedule 13D”).
 
	Item 1.	Security and Issuer.	
 
This statement relates to the Class B Common Stock, par value $0.0001 per share (the “Shares”), of Castlight Health, Inc., a Delaware corporation (“Castlight” or the “Issuer”). The address of the principal executive offices of the Issuer is 150 Spear Street, Suite 400, San Francisco, California 94105.
 
	Item 2.	Identity and Background.	
 
(a)       This statement is filed by Raging Capital Management, LLC, a Delaware limited liability company (“Raging Capital”), and William C. Martin. Each of the foregoing is referred to as a “Reporting Person” and collectively as the “Reporting Persons.”
 
Raging Capital is the Investment Manager of Raging Capital Master Fund, Ltd., a Cayman Islands exempted company (“Raging Master”), in whose name the Shares are held. William C. Martin is the Chairman, Chief Investment Officer and Managing Member of Raging Capital. Raging Master has delegated to Raging Capital the sole authority to vote and dispose of the securities held by Raging Master pursuant to an Investment Management Agreement, dated November 9, 2012, as amended and restated on December 21, 2016 (the “IMA”). The IMA may be terminated by any party thereto effective at the close of business on the last day of any fiscal quarter by giving the other party not less than sixty-one days’ written notice. As a result, each of Raging Capital and William C. Martin may be deemed to beneficially own the Shares held by Raging Master.
 
Set forth on Schedule A annexed hereto (“Schedule A”) is the name and present principal business, occupation or employment and the name, principal business and address of any corporation or other organization in which such employment is conducted of the executive officers of Raging Capital. To the best of the Reporting Persons’ knowledge, except as otherwise set forth herein, none of the persons listed on Schedule A beneficially owns any securities of the Issuer or is a party to any contract, agreement or understanding required to be disclosed herein.
 
(b)       The address of the principal office of each of the Reporting Persons is Ten Princeton Avenue, P.O. Box 228, Rocky Hill, New Jersey 08553.
 
(c)       The principal business of Raging Capital is serving as the Investment Manager of Raging Master. The principal occupation of William C. Martin is serving as the Chairman, Chief Investment Officer and Managing Member of Raging Capital.
 
(d)       No Reporting Person nor any person listed on Schedule A has, during the last five years, been convicted in a criminal proceeding (excluding traffic violations or similar misdemeanors).
 
(e)       No Reporting Person nor any person listed on Schedule A has, during the last five years, been party to a civil proceeding of a judicial or administrative body of competent jurisdiction and as a result of such proceeding was or is subject to a judgment, decree or final order enjoining future violations of, or prohibiting or mandating activities subject to, federal or state securities laws or finding any violation with respect to such laws.
 
(f)       Raging Capital is organized under the laws of the State of Delaware. William C. Martin is a citizen of the United States of America.

4
CUSIP No. 14862Q 10 0
 
	Item 3.	Source and Amount of Funds or Other Consideration.	
 
The aggregate purchase price of the 10,423,517 Shares owned directly by Raging Master is approximately $14,834,429, including brokerage commissions. Such Shares were acquired with the working capital of Raging Master.
 
Raging Master effects purchases of securities primarily through margin accounts maintained for it with prime brokers, which may extend margin credit to it as and when required to open or carry positions in the margin accounts, subject to applicable federal margin regulations, stock exchange rules and the prime brokers’ credit policies. In such instances, the positions held in the margin accounts are pledged as collateral security for the repayment of debit balances in the accounts.
 
	Item 4.	Purpose of Transaction.	
 
In these uncertain times, Raging Capital calls upon Castlight’s management and board to take immediate and aggressive steps to reduce costs across all facets of the business and to drive the business to near-term break-even or better. This would protect Castlight’s strong balance sheet (cash + marketable securities currently account for over half of the company’s market cap) and secure the long-term viability of the business.
 
Depending upon management’s and the board’s ability to execute on the above, overall market conditions, other investment opportunities available to the Reporting Persons, and the availability of securities of the Issuer at prices that would make the purchase or sale of securities of the Issuer desirable, the Reporting Persons may endeavor to increase or decrease their position in the Issuer, directly or through their affiliates, through, among other things, the purchase or sale of securities of the Issuer on the open market or in private transactions or otherwise, on such terms and at such times as the Reporting Persons may deem advisable.
 
No Reporting Person has any present plan or proposal which would relate to or result in any of the matters set forth in subparagraphs (a) - (j) of Item 4 of Schedule 13D other than as set forth herein or such as would occur upon completion of any of the actions discussed herein. The Reporting Persons intend to review their investment in the Issuer on a continuing basis and may from time to time engage in discussions with management and the board concerning, among other things, the business, operations and future plans of the Issuer. Depending on various factors including, without limitation, the Issuer’s financial position and investment strategy, the price levels of the securities of the Issuer, conditions in the securities markets and general economic and industry conditions, the Reporting Persons may in the future take such actions with respect to their investment in the Issuer as they deem appropriate, directly or through their affiliates, including, without limitation, engaging in communications with management and the board of the Issuer, engaging in discussions with shareholders of the Issuer and others about the Issuer and the Reporting Persons’ investment, making proposals concerning changes to the capitalization, capital allocation strategy, ownership structure, board composition or operations of the Issuer, purchasing additional securities of the Issuer, selling some or all of their securities of the Issuer or engaging in short selling of or any hedging or similar transaction with respect to the securities of the Issuer, or changing their intention with respect to any and all matters referred to in Item 4.
 
	Item 5.	Interest in Securities of the Issuer.	
 
(a)       The aggregate percentage of Shares reported owned by each person named herein is based upon 114,227,876 Shares outstanding as of February 25, 2020, which is the total number of Shares outstanding as reported in the Issuer’s Form 10-K filed with the Securities and Exchange Commission on February 28, 2020.

5
CUSIP No. 14862Q 10 0
 
As of the close of business on March 27, 2020, each of Raging Capital and William C. Martin may be deemed to beneficially own the 10,423,517 Shares, constituting approximately 9.1% of the Shares outstanding, held by Raging Master by virtue of their relationships with Raging Master discussed in further detail in Item 2.
 
The filing of this Schedule 13D shall not be deemed an admission that the Reporting Persons are, for purposes of Section 13(d) of the Securities Exchange Act of 1934, as amended, the beneficial owners of any Shares he or it does not directly own. Each of the Reporting Persons specifically disclaims beneficial ownership of the Shares reported herein that he or it does not directly own. Without limiting the foregoing sentence, Raging Master specifically disclaims beneficial ownership of the securities of the Issuer held by it by virtue of its inability to vote or dispose of such securities as a result of the IMA.
 
(b)       Raging Capital and William C. Martin may be deemed to share the power to vote and dispose of the Shares held by Raging Master.
 
(c)       Schedule B annexed hereto lists all transactions in the Shares during the past sixty days by the Reporting Persons. All of such transactions were effected in the open market.
 
(d)        No person other than the Reporting Persons is known to have the right to receive, or the power to direct the receipt of dividends from, or proceeds from the sale of, the Shares.
 
(e)        Not applicable.
 
	Item 6.	Contracts, Arrangements, Understandings or Relationships With Respect to Securities of the Issuer.	
 
On March 30, 2020, the Reporting Persons entered into a Joint Filing Agreement in which the Reporting Persons agreed to the joint filing on behalf of each of them of statements on Schedule 13D with respect to the securities of the Issuer. A copy of this agreement is attached as an exhibit hereto and is incorporated herein by reference.
 
	Item 7.	Material to be Filed as Exhibits.	
 
	99.1	Joint Filing Agreement by and between Raging Capital Management, LLC and William C. Martin, dated March 30, 2020.	
 
	99.2	Powers of Attorney.	

6
CUSIP No. 14862Q 10 0
 
SIGNATURES
 
After reasonable inquiry and to the best of his knowledge and belief, each of the undersigned certifies that the information set forth in this statement is true, complete and correct.
 
Dated:  March 30, 2020	Raging Capital Management, LLC	
 	 	
 	By:	/s/ Frederick C. Wasch	
 	 	Name:	Frederick C. Wasch	
 	 	Title:	Chief Financial Officer	
 
 	/s/ Frederick C. Wasch	
 	Frederick C. Wasch as attorney-in-fact for William C. Martin	

7
CUSIP No. 14862Q 10 0
 
SCHEDULE A
 
Executive Officers of Raging Capital Management, LLC
 
Name and Position	Present Principal Occupation	Business Address	
 	 	 	
William C. Martin, 
Chairman, Chief Investment
Officer and Managing Member	Chairman, Chief Investment Officer and Managing Member of Raging Capital Management, LLC	c/o Raging Capital Management, LLC
Ten Princeton Avenue, P.O. Box 228
Rocky Hill, New Jersey 08553	
Frederick C. Wasch,
Chief Financial Officer	Chief Financial Officer of Raging Capital Management, LLC	c/o Raging Capital Management, LLC
Ten Princeton Avenue, P.O. Box 228
Rocky Hill, New Jersey 08553	

8
CUSIP No. 14862Q 10 0
 
SCHEDULE B
 
Transactions in the Shares of the Issuer During the Past 60 Days
 
Class of
Security	Shares Purchased/(Sold)	Price ($)	Date of
Purchase/Sale	
 
RAGING CAPITAL MASTER FUND, LTD.
 
Common Stock	(212,980)	1.0050	03/04/2020	
Common Stock	(12,672)	1.0085	03/05/2020	

9

 
Exhibit 99.1
 
JOINT FILING AGREEMENT
 
In accordance with Rule 13d-1(k)(1)(iii) under the Securities Exchange Act of 1934, as amended, the persons named below agree to the joint filing on behalf of each of them of a Statement on Schedule 13D (including amendments thereto) with respect to the Class B Common Stock, par value $0.0001 per share, of Castlight Health, Inc. This Joint Filing Agreement shall be filed as an Exhibit to such Statement.
 
Dated:  March 30, 2020	Raging Capital Management, LLC	
 	 	
 	By:	/s/ Frederick C. Wasch	
 	 	Name:	Frederick C. Wasch	
 	 	Title:	Chief Financial Officer	
 
 	/s/ Frederick C. Wasch	
 	Frederick C. Wasch as attorney-in-fact for William C. Martin	

Exhibit 99.2
 
POWER OF ATTORNEY
 
Know all by these presents, that the undersigned hereby constitutes and appoints Frederick C. Wasch signing singly, the undersigned’s true and lawful attorney-in-fact to:
 
1.       Execute for and on behalf of the undersigned all documents relating to the business of Raging Capital Management, LLC including, but not limited to, all filings with the Securities and Exchange Commission, any stock exchange and any other regulatory, administrative or similar authority, and all memoranda, correspondence, communications or the like, except that such attorney-in-fact shall have no power to execute any document that has the effect of creating a financial commitment or financial obligation of Raging Capital Management, LLC or its affiliates.
 
2.       Do and perform any and all acts for and on behalf of the undersigned that may be necessary or desirable to complete and execute any such document, complete and execute any amendment or amendments thereto, and timely file such document with the appropriate authority.
 
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 such attorney-in-fact’s discretion.
 
The undersigned hereby grants to such attorney-in-fact full power and authority to do and perform any and every act and thing whatsoever requisite, necessary, or 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 such attorney-in-fact’s 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 the foregoing attorney-in-fact, in serving in such capacity at the request of the undersigned, is not assuming any of the undersigned’s responsibilities to comply with any rules or regulations, including federal securities laws.
 
This Power of Attorney shall remain in full force until revoked by the undersigned in a signed writing delivered to the foregoing attorney-in-fact.
 
[Signatures on Following Page]

 
IN WITNESS WHEREOF, the undersigned has caused this Power of Attorney to be executed as of this 30th day of December, 2014.
 
 	/s/ William C. Martin	
 	William C. Martin	

 
POWER OF ATTORNEY
 
Know all by these presents, that each of the undersigned hereby constitutes and appoints Allan J. Young signing singly, the undersigned’s true and lawful attorney-in-fact to:
 
1.       Execute for and on behalf of the undersigned all documents relating to the business of Raging Capital Management, LLC, including, but not limited to, all filings with the Securities and Exchange Commission, any stock exchange and any other regulatory, administrative or similar authority, and all memoranda, correspondence, communications or the like, except that such attorney-in-fact shall have no power to execute any document that has the effect of creating a financial commitment or financial obligation of the undersigned or their affiliates.
 
2.       Do and perform any and all acts for and on behalf of the undersigned that may be necessary or desirable to complete and execute any such document, complete and execute any amendment or amendments thereto, and timely file such document with the appropriate authority.
 
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 such attorney-in-fact’s discretion.
 
Each of the undersigned hereby grants to such attorney-in-fact full power and authority to do and perform any and every act and thing whatsoever requisite, necessary, or 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 such attorney-in-fact’s 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. Each of the undersigned acknowledges that the foregoing attorney-in-fact, in serving in such capacity at the request of the undersigned, is not assuming any of the undersigned’s responsibilities to comply with any rules or regulations including federal securities laws.
 
This Power of Attorney shall remain in full force and effect until revoked by the undersigned in a signed writing delivered to the foregoing attorney-in-fact.
 
[Signatures on Following Page]

 
IN WITNESS WHEREOF, the undersigned has caused this Power of Attorney to be executed as of this 26th day of February, 2015.
 
 	Raging Capital Management, LLC	
 	 	
 	By:	/s/ William C. Martin	
 	 	Name:	William C. Martin	
 	 	Title:	Managing Member	
 
 	/s/ William C. Martin	
 	William C. Martin