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February 4, 2016

Priya Jain

Dear Priya,

Congratulations! On behalf of Castlight Health, Inc., a Delaware corporation
(the “Company”), I am pleased to offer you the position of Chief Accounting
Officer, reporting to Siobhan Nolan Mangini. This position will be located at
our San Francisco office. Your anticipated start date will be March 21, 2016.

Your total rewards package is as follows:
Base Salary: $245,000.00 annually
Bonus Target: 30%
RSU: 80,000
Sign On Bonus: $20,000 (payable concurrent with your first scheduled payroll
following your start date). In addition, in the event your employer asks for a
"reclaw" of your sign on bonus for joining their organization, Castlight will
reimburse you up to $15,000 (payable concurrent with your first scheduled
payroll following your start date).

This offer is conditional on satisfactory results of a routine background check,
satisfactory results of reference checks, and other matters mentioned below.
Your income is subject to applicable withholdings and deductions, payable in
accordance with the Company’s standard payroll schedule and procedures.
Castlight Health’s Annual Bonus Program will be prorated for the 2016
performance year. New hire eligibility bonuses are contingent upon a start date
prior to October 1st. If hired after October 1st, new hires will be eligible
after completing employment of an entire full fiscal year (January through
December). The percentage amount, as stated above, may change in future years.
Your award will be based on your individual contribution to both the Company’s
goals and objectives as well as your individual goals and objectives and is not
guaranteed.

In the event that you voluntarily leave Castlight Health within 12 months of
your date of hire, you will be responsible for reimbursing the company for 100%
of your signing bonus and/or relocation disbursement. By your signature on this
offer letter, you agree to pay back any monies received relating to your overall
disbursement.

As a regular employee of the Company, you will be eligible to participate in
Company sponsored benefits generally available to regular employees. You shall
also be reimbursed in accordance with the Company’s expense reimbursement
policies for all documented reasonable business expenses that are incurred in
connection with carrying out your duties for the Company and in compliance with
Company policy. At Castlight we do not have a formal paid vacation, personal and
sick-time policy. Instead, we have a flexible time-off policy pursuant to which
we encourage you to take time-off and to work with your manager on the timing.

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Subject to the approval of the Company’s Board of Directors, you will be awarded
restricted stock units, as stated above, to acquire shares of Company Class B
Common Stock ("RSUs") under its 2014 Equity Incentive Plan (“Plan”). An award of
RSUs gives you the right to receive shares of Company Class B Common Stock upon
vesting and settlement of the RSUs. Your grant will be issued during the first
open window following your start date. The RSUs are subject to a four-year
vesting schedule with 25% of the RSUs vesting after one year from the grant date
and the remainder of the RSUs vesting quarterly thereafter, provided you remain
in continuous service on each applicable vesting date, as set forth in the
applicable RSU award agreement. On each vesting date, the shares subject to the
RSUs, which are vested, will be issued within 30 days following the applicable
vesting date. Upon receipt of the shares by you upon settlement of the RSUs, you
will be subject to tax based on the fair market value of such shares on the date
of settlement and the Company must satisfy its tax withholding obligations in a
manner satisfactory to the Company before any shares are issued to you. The
award of RSUs by the Company is subject to the Board of Directors approval and
this promise to recommend such approval is not a promise of compensation and is
not intended to create any obligations on the part of the Company. The RSUs will
be governed by the terms of the Plan and your RSU award agreement, both of which
will be provided to you upon approval of such award by the Company’s Board of
Directors.

Your employment pursuant to this offer is contingent upon you providing the
Company with the legally required proof of your identity and authorization to
work in the United States, upon your signing and agreeing to be bound by the
enclosed At-Will Employment, Confidential Information, Invention Assignment and
Arbitration Agreement, and upon completion of a basic background check as
required by the Company to protect privacy of sensitive user information.

While we hope that your employment with the Company will be mutually
satisfactory, employment with the Company is for no specific period of time. As
a result, either you or the Company is free to terminate your employment
relationship at any time for any reason, with or without cause. This is the full
and complete agreement between you and the Company on this term. Although your
job duties, title, compensation and benefits, as well as the Company’s personnel
policies and procedures, may change from time-to-time, the “at will” nature of
your employment may not be changed except by an express writing signed and dated
by both you and the Chief Executive Officer of the Company.

This letter when signed by you sets forth the terms of your employment with us
and supersedes any prior representations or agreements, whether written or oral.
To accept and execute this offer, please sign and return within five days from
the date of this letter.

We look forward to you joining Castlight Health!

If you have any questions, please call me at 415.813.0796.

Sincerely,
John Bush
Head of Talent Acquisition

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I have read, understand, and accept this employment offer. Furthermore, in
choosing to accept this offer, I agree that I am not relying on any
representations, whether verbal or written, except as specifically set out
within this letter.

/s/ Priya Jain     
Employee Signature

Priya Jain
Printed Name

Date: 2/4/16