CSLT Castlight Health Inc

The following constitutes Amendment No. 1 to the Schedule 13D filed by the undersigned (“Amendment No. 1”). This Amendment No. 1 amends the Schedule 13D as specifically set forth herein.

The final paragraph of Item 2(a) is hereby amended and restated to read as follows:

Set forth on Schedule A annexed to this Amendment No. 1 (“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.

Item 3 is hereby amended and restated to read as follows:

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.

The aggregate purchase price of the 605,000 Shares beneficially owned directly by Mr. Martin is approximately $411,561, including brokerage commissions. Such Shares were acquired with personal funds.

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 is hereby amended to add the following:

On June 9, 2020, Raging Capital sent a letter to the board of directors of the Issuer (the “June letter”) following up on a private letter previously sent to the board in April 2020 (the “April letter”) expressing its serious concerns regarding the lack of cost consciousness and profitability at the Issuer and imploring the board to take decisive action to address these concerns. Although Raging Capital was pleased to see some of the incremental cost cuts announced by the Issuer after the April letter was sent, Raging Capital expressed its surprise and disappointment that none of the board members reached out to it, as specifically requested, to discuss an action plan that could be immediately implemented by the Issuer. Raging Capital also discussed the alarming results of the recent annual meeting of shareholders, including a withhold vote of over 20% of the votes cast on the two independent directors up for election, more than 23 million shares voted against the appointment of Ernst & Young (“E&Y”) as the Issuer’s auditor and management’s failure to obtain the requisite vote to approve the non-binding advisory proposal on executive compensation. Raging Capital encouraged the board to act with a greater sense of urgency to address its concerns or else risk facing a proxy campaign in the fall. Raging Capital referred the board to its April letter outlining the Issuer’s egregious cost structure and ideas on how to streamline and rationalize the business in order to drive immediate profitability, including replacing E&Y.

A copy of the June letter, including the April letter, are attached hereto as Exhibit 99.1 and incorporated herein by reference.

Items 5(a)-(c) are hereby amended and restated to read as follows:

(a)       The aggregate percentage of Shares reported owned by each person named herein is based upon 114,484,826 Shares outstanding as of May 5, 2020, which is the total number of Shares outstanding as reported in the Issuer’s Form 10-Q filed with the Securities and Exchange Commission on May 8, 2020.

As of the close of business on June 8, 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. As of the close of business on June 8, 2020, Mr. Martin also directly beneficially owns an additional 605,000 Shares which, together with the Shares held by Raging Master, constitutes approximately 9.6% of the Shares outstanding.

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. Mr. Martin has the power to vote and dispose of the Shares he directly beneficially owns.

(c)       Schedule B annexed hereto lists all transactions in the Shares during the past sixty days by the Reporting Persons and the other executive officer of Raging Capital disclosed in Schedule A. All of such transactions were effected in the open market.

Item 7 is hereby amended to add the following exhibit:

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.

SCHEDULE A

Executive Officers of Raging Capital Management, LLC

¹As of the close of business on June 8, 2020, Mr. Wasch may be deemed to beneficially own 18,545 Shares, including Shares held by his spouse. The aggregate purchase price of such Shares is approximately $12,980. Such Shares were purchased with personal funds. A list of all transactions in the Shares by Mr. Wasch during the past sixty days are set forth in Schedule B.

SCHEDULE B

Transactions in the Shares of the Issuer During the Past 60 Days

WILLIAM C. MARTIN

FREDERICK C. WASCH