On January 4, 2017, Castlight Health, Inc. (Castlight or the
Company) entered into an Agreement and Plan of Merger and
Reorganization (the Merger Agreement) with Neptune Acquisition
Subsidiary, Inc., a Delaware corporation and wholly owned
subsidiary of Castlight (Merger Sub), Jiff, Inc., a Delaware
corporation (Jiff) and Fortis Advisors LLC, as the Stockholders
Agent, to which Merger Sub will merge with and into Jiff with Jiff
surviving the merger as a wholly owned subsidiary of Castlight (the
Merger).

Subject to the terms and conditions set forth in the Merger
Agreement, upon the consummation of the Merger, all outstanding
capital stock and vested options of Jiff will be exchanged for an
aggregate of approximately 27,000,000 shares, and options
exercisable to purchase shares, of Castlight Class B Common Stock,
subject to certain adjustments as set forth in the Merger
Agreement, and the right to receive up to 4,000,000 shares of
Castlight Class B Common Stock upon the achievement by the Jiff
business of certain milestones in 2017. Former Jiff equityholders
will receive an aggregate of 1,000,000 shares of Castlight Common
Stock if the Jiff business achieves at least $25 million in revenue
in 2017 and an aggregate of 3,000,000 shares of Castlight Common
Stock if the Jiff business achieves at least $25 million in net new
bookings during 2017. All options for Jiff common stock and Jiff
restricted stock units held by Jiff employees who become continuing
employees of the combined company will be converted into options to
purchase Castlight Class B Common Stock and Castlight restricted
stock units, respectively.

The Merger Agreement contains customary representations, warranties
and covenants by Castlight, the Merger Sub and Jiff and is subject
to certain closing conditions, including, among other things,
approval by the stockholders of Castlight of the issuance of
Castlight Class B Common Stock in connection with the Merger. to
the Merger Agreement, following the closing of the Merger (the
Closing), certain securityholders of Jiff have agreed to indemnify
Castlight for any losses related to certain matters, including,
among other things, failures of Jiffs representations and
warranties in the Merger Agreement to be true and correct, failure
by Jiff to comply with its covenants in the Merger Agreement, and
other specified matters. As partial security for such
indemnification obligations, the parties have agreed to deposit
2,700,000 shares of Castlight Class B Common Stock in a separate
escrow fund for a period of 12 months after Closing.

Upon the Closing, the Board of Directors (Board) of Castlight will
include two members designated by Jiff.

In connection with the Merger Agreement, certain stockholders of
Castlight holding approximately>44.2% of the voting power of
Castlight (collectively, the Designated Equityholders) have entered
into a support agreement with Jiff (the Support Agreement). The
Support Agreement places certain restrictions on the transfer of
the shares of common stock of Castlight (and options exercisable
therefor) held by the Designated Equityholders and includes
covenants regarding the voting of such shares, including an
agreement to vote in favor of the issuance of shares of Castlight
Class B Common Stock and related matters and against competing
acquisition proposals. Additionally, certain stockholders of Jiff
holding approximately: (a) 68.0% of Jiff common stock, Jiff
preferred stock and Jiff starter stock, voting together as a single
voting class), (b) 22.5% of the outstanding shares of Jiff common
stock, and (c) 68.7% of the outstanding shares of Jiff preferred
stock and starter stock (voting together as a single class)
(collectively, the Jiff Designated Equityholders) have entered into
a support agreement with Castlight (the Stockholder Agreement). The
Stockholder Agreement places certain restrictions on the transfer
of the capital stock of Jiff (and options exercisable therefor)
held by the Jiff Designated Equityholders and includes covenants
regarding the voting of such shares, including an agreement to vote
in favor of the Merger and the adoption of the Merger Agreement and
related matters and against competing acquisition proposals.

Also in connection with the Merger Agreement, the Designated
Equityholders, the Jiff Designated Equityholders and certain
officers of Castlight each entered into a Lock-up Agreement with
Castlight to which such parties have agreed, except in limited
circumstances, not to sell or transfer, or engage in swap or
similar transactions with respect to, shares of Castlights capital
stock, including, as applicable, shares received in connection with
the Merger, for a period ending on the earlier of (a) 90 days
following the Closing or (b) July 2, 2017.

The preceding summary is qualified in its entirety by reference to
the Merger Agreement and the forms of Support Agreement,
Stockholder Agreement and Lock-up Agreement, which are filed as
Exhibits 2.1, 10.1, 10.2 and 10.3, respectively, and incorporated
herein by reference. The Merger Agreement has been attached as an
exhibit to this Current Report on Form 8-K to provide investors and
securityholders with information regarding its terms. It is not
intended to provide any other factual information about Castlight
or Jiff or to modify or supplement any factual disclosures about
Castlight in its public reports filed with the Securities and
Exchange Commission (SEC). The Merger Agreement includes
representations, warranties and covenants of Castlight and Jiff
made solely for the purpose of the Merger Agreement and solely for
the benefit of the other parties thereto in connection with the
negotiated terms of the Merger Agreement. Investors should not rely
on the representations, warranties and covenants in the Merger
Agreement or any descriptions thereof as characterizations of the
actual state of facts or conditions of Castlight or Jiff, or any of
their respective subsidiaries or affiliates. Moreover, certain of
those representations and warranties may not be accurate or
complete as of any specified date, may be subject to a contractual
standard of materiality different from those generally applicable
to SEC filings or may have been used for purposes of allocating
risk among the parties to the Merger Agreement, rather than
establishing matters of fact.

Item 2.02 Results of Operations and Financial Condition.

On January 4, 2017, Castlight and Jiff issued a joint press release
announcing the Merger (the Joint Press Release). In the Joint Press
Release, the Company disclosed that it expects to report full year
2016 revenue of approximately $102 million, which is the high-end
of its previously issued guidance range. This reflects the Companys
estimates based solely upon information available to it as of the
date of this Current Report on Form 8-K, is not a comprehensive
statement of its financial results or position as of or for the
year ended December 31, 2016, and has not been audited, reviewed or
compiled by the Companys independent registered public accounting
firm.

The Joint Press Release is being furnished as Exhibit 99.1 to this
Current Report on Form 8-K and is incorporated herein by reference.

The information in this Item 2.02, including Exhibit 99.1 to this
Current Report on Form 8-K, shall not be deemed to be filed for
purposes of Section 18 of the Securities Exchange Act of 1934, as
amended, or otherwise subject to the liabilities of that section or
Sections 11 and 12(a)(2) of the Securities Act of 1933, as amended.
The information contained in this Item 2.02 and in the accompanying
Exhibit 99.1 shall not be incorporated by reference into any
registration statement or other document filed by Castlight with
the SEC, whether made before or after the date of this Current
Report on Form 8-K, regardless of any general incorporation
language in such filing (or any reference to this Current Report on
Form 8-K generally), except as shall be expressly set forth by
specific reference in such filing.

Item 5.02 Departure of Directors or Certain Officers; Election of
Directors; Appointment of Certain Officers; Compensatory
Arrangements of Certain Directors.

(b)

The information set forth below under Item 5.02(c) is hereby
incorporated by referenced into this Item 5.02(b).

In connection with the Merger, Ann Lamont, a member of the Board of
the Company, notified the Company of her decision to resign from
the Board, effective at the Closing. Ms. Lamont serves on the Audit
Committee. Ms. Lamonts decision to resign, to the knowledge of the
Companys executive officers, was not the result of any disagreement
with the Company on any matter relating to the Companys operations,
policies or practices.

(c)

On January 4, 2017, the Board of the Company, in connection with
the Merger, approved the appointment of Giovanni Colella as
Executive Chairman, John C. Doyle as Chief Executive Officer, and
Derek Newell as President of the Company, in

each case to be effective at the Closing. Mr. Colella and Mr. Doyle
were appointed to these positions from other positions with the
Company as described below. Following the Closing, although no
person will hold the title of Chief Operating Officer, Mr. Doyle
will continue to take on the duties and responsibilities of
principal operating officer.

At this time, the Board has not approved any changes to Mr.
Colellas compensation in connection with his transition to becoming
Executive Chairman.

There are no arrangements or understandings between Mr. Newell and
any other persons to which Mr. Newell was named as an officer,
other than the Merger Agreement. To the Companys knowledge, Mr.
Newell is not a party to any transaction required to be disclosed
to Item 404(a) of Regulation S-K. In connection with his
appointment as President, Mr. Newell will execute the Companys
standard form of indemnification agreement for executive officers.

Giovanni M. Colella>co-founded Castlight in 2008 and previously
served as its Chief Executive Officer and a director since that
time. Prior to founding Castlight, Dr. Colella served as Founder,
President and Chief Executive Officer of RelayHealth Corporation, a
health care technology company, from 2000 until its acquisition in
2006. Dr. Colella holds an M.D. from the Universita Degli Studi di
Milano in Italy and an M.B.A. from Columbia Business School.

John C. Doyle previously served as Castlight’s President since
July 2016 and as its Chief Operating Officer since November 2015,
and prior to that as its Chief Financial Officer, Vice President
and Treasurer from November 2012 until July 2016. Previously, Mr.
Doyle served as Chief Financial Officer and then Chief Operating
Officer of Achaogen, Inc., a biopharmaceutical company, from August
2009 to November 2012. Prior to joining Achaogen, Mr. Doyle was
Vice President, Finance and Corporate Planning at Genentech, Inc.
from July 2007 to June 2009. Mr. Doyle previously served in various
roles at Renovis, Inc., from 2002 to June 2007, ultimately as its
Senior Vice President of Corporate Development and Chief Financial
Officer. Mr. Doyle has been a member of the board of directors of
Achaogen since November 2012 and a member of its compensation
committee since January 2016. Mr. Doyle holds a B.S. in Business
Administration from California Polytechnic State University, San
Luis Obispo, and an M.B.A. from the Haas School of Business at the
University of California, Berkeley.

Derek Newell has been the Chief Executive Officer of Jiff since
November 2011. Prior to that he was the President at Robert Bosch
Healthcare Systems, Inc., a telehealth systems company, from 2008
to 2011. Before that, he was Chief Marketing Officer at
LifeMasters, a disease management/population health management
company, from 2006 to 2011. Mr. Newell holds B.S. in Molecular
Cellular Biology (Biochemistry) from the University of California
at Berkeley, an M.B.A. from the Haas School of Business at the
University of California, Berkeley, and an M.P.H. from the
University of California, Berkeley.

Item 7.01 Regulation FD Disclosure

On January 4, 2017, Castlight and Jiff issued the Joint Press
Release, which is being furnished as Exhibit 99.1 to this Current
Report on Form 8-K and is incorporated herein by reference.

On January 4, 2017, Castlight and Jiff, Inc. each provided FAQs
with respect to the Merger to their respective employees announcing
Castlights proposed acquisition of Jiff, Inc. In addition, on
January 4, 2017, each of Mr. Colella and Mr. Doyle sent
correspondence by e-mail transmission to Castlights employees, and
Mr. Newell sent correspondence by e-mail transmission to Jiffs
employees. Copies of the eFAQs provided to Castlight and Jiff
employees are furnished as Exhibits 99.2 and 99.3, respectively, to
this Current Report on Form 8-K and are incorporated herein by
reference. Copies of the email correspondence sent by Mr. Colella,
Mr. Doyle and Mr. Newell are furnished as Exhibits 99.4, 99.5 and
99.6, respectively, to this Current Report on Form 8-K and are
incorporated herein by reference.

The information contained in this Item 7.01 and Exhibits 99.1,
99.2, 99.3, 99.4, 99.5 and 99.6 to this report shall not be deemed
to be filed for purposes of Section 18 of the Securities Exchange
Act of 1934, as amended, or otherwise subject

to the liability of that section, and shall not be incorporated by
reference into any filings made by Castlight under the Securities
Act of 1933, as amended, or the Securities Exchange Act of 1934, as
amended, except as may be expressly set forth by specific reference
in such filing.

Item 9.01 Financial Statements and Exhibits.

(d)>Exhibits

* Schedules have been omitted to Item 601(b)(2) of Regulation
S-K. Castlight agrees to furnish supplementally a copy of such
schedules, or any section thereof, to the SEC upon request.

Forward Looking Statements

This report and its attached exhibits contains forward-looking
statements that are not purely historical regarding the Companys or
its managements intentions, beliefs, expectations and strategies
for the future, including those relating to its expected financial
results for the year ended December 31, 2016, the closing of the
proposed transaction and the expected closing date of the proposed
transaction, the anticipated benefits of the proposed transaction,
and anticipated future combined operations, products and services
of the Company and Jiff. Because such statements deal with future
events, they are subject to various risks and uncertainties, and
actual results could differ materially from the Companys current
expectations. Factors that could cause actual results to differ
materially include risks and uncertainties such as those relating
to the ability of the parties to complete the proposed transaction,
obtaining Company and Jiff stockholder approval and required
regulatory clearances, and customer and partner reception to the
proposed transaction. Readers should also refer to the section
entitled Risk Factors in the Companys Annual Report on Form 10-K,
its most recent Quarterly Report on Form 10-Q, and its other
reports filed with the SEC.

All forward-looking statements included in this report and attached
exhibits are made as of the date of this report, based on
information currently available to the Company, and the Company
assumes no obligation to update any such forward-looking statement
or reasons why results may differ.

Important Additional Information will be Filed with the SEC

In connection with the proposed transaction between the Company and
Jiff, the Company intends to file a registration statement on Form
S-4 with the SEC. This registration statement will contain a joint
proxy statement/prospectus/information statement and relevant
materials concerning the proposed transaction. Additionally, the
Company intends to file with the SEC other relevant materials in
connection with the proposed transaction. After the registration
statement is declared effective by the SEC, the Company and Jiff
will deliver a definitive joint proxy
statement/prospectus/information statement to their respective
stockholders. STOCKHOLDERS OF THE COMPANY AND JIFF ARE URGED TO
READ ALL RELEVANT DOCUMENTS FILED WITH THE SEC, INCLUDING THE
DEFINITIVE JOINT PROXY STATEMENT/PROSPECTUS/INFORMATION STATEMENT,
BECAUSE THEY WILL CONTAIN IMPORTANT INFORMATION ABOUT THE PROPOSED
TRANSACTION. Investors and security holders will be able to obtain
the documents free of charge at the SECs web site,
http://www.sec.gov. Documents will also be available for free from
the Company at www.castlighthealth.com.

This communication shall not constitute an offer to sell or the
solicitation of an offer to sell or the solicitation of an offer to
buy any securities, nor shall there be any sale of securities in
any jurisdiction in which such offer, solicitation or sale would be
unlawful prior to registration or qualification under the
securities laws of any such jurisdiction. No offering of securities
in connection with the proposed transaction shall be made except by
means of a prospectus meeting the requirements of Section 10 of the
Securities Act of 1933, as amended.

The Company and its executive officers and directors may be deemed
to be participants in the solicitation of proxies from the Companys
stockholders with respect to the matters relating to the proposed
transaction. Jiff and its officers and directors may also be deemed
a participant in such solicitation. Information regarding any
interest that the Company, Jiff or any of the executive officers or
directors of the Company or Jiff may have in the proposed
transaction with Jiff will be set forth in the joint proxy
statement/prospectus/information statement that the Company intends
to file with the SEC in connection with its stockholder vote on
matters relating to the proposed transaction. Information about the
directors and executive officers of the Company, including their
respective interest in security holding of the Company, is set
forth in the proxy statement for the Companys 2016 Annual Meeting
of Stockholders, which was filed with the SEC on April 29, 2016.
Stockholders may obtain additional information regarding the
interest of such participants by reading the definitive joint proxy
statement/prospectus/information statement regarding the proposed
transaction when it becomes available. These documents can be
obtained free of charge from the sources indicated above.