Document:

EX-10.7

 Exhibit 10.7 

JOB OFFER LETTER 
 September 6, 2013

 Michele Law 
 Via Email 

Dear Michele: 
 On behalf of Castlight Health,
Inc., a Delaware corporation (the “Company”), I am pleased to offer you, conditional on satisfactory results of a routine background check and other matters mentioned below, a position as a Chief Revenue Officer, at a starting salary of
$250,000 per year, subject to applicable withholdings and deductions, payable in accordance with the Company’s standard payroll schedule and procedures. You will also be eligible for incentive compensation with an annual target of 60% of base
salary. Your incentive compensation will be based on the achievement of the Company’s goals and objectives as well as the achievement of individual objectives set by you and your manager in the first 30 days of employment. The assessment of the
achievement of the goals and objectives is determined by the Company and as the same may be amended by the Company from time to time. You must be employed with us on the date of the payout to fully earn and receive any payouts under the plan. Your
incentive compensation for 2013 will be pro-rated based on your start date. 
 If you accept this offer, your start date is to be determined and you will
report to Randy Womack, Chief Operating Officer. Your primary duties as a member of the Executive Committee will be to contribute valuable insight, expertise and experience to key decisions, including building a revenue and sales strategy
linked with our long-term corporate strategy to ensure that the entire organization has the direction, information, resources and support to successfully execute in the field. As the executive with primary responsibility for revenue growth, you
will lead the Sales, Field Enablement, Sales Support, Marketing and Customer Success teams. Of course, the Company may modify your responsibilities, title and compensation from time to time, as it deems necessary. 

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. 

 Subject to the approval of the Company’s Board of Directors, you shall be granted an option
(the “Option”) to purchase 810,000 shares of the Company’s stock. The shares will be at an exercise price equal to the fair market value of such shares on the date of grant as determined by the Company’s Board of Directors. The
Option shall be granted pursuant to and upon the terms set forth in the Company’s stock incentive plan and your stock option agreement and shall have a maximum term of 10 years (subject to earlier termination in connection with a termination of
your employment or a change in control of the Company). So long as you remain actively employed by the Company, the Option shall vest: (a) with respect to 20% of the underlying shares on the one-year anniversary of your employment start date;
(b) during your second year of employment in 12 installments of 1.667% of the underlying shares upon your completion of each additional consecutive month of service; and (c) with respect to the balance, in 24 substantially equal
installments upon your completion of each additional consecutive month of service. Among other terms and conditions set forth in the Company’s stock incentive plan and your stock option agreement, the shares underlying the Option will be
subject to rights of first refusal and a market standoff agreement, and your exercise of the Option is conditioned upon your execution of the Amended and Restated Voting Agreement, dated April 26, 2012, by and among the Company and the parties
thereto, as may be amended from time to time, and the Amended and Restated Right of First Refusal and Co-Sale Agreement, dated April 26, 2012, by and among the Company and the parties thereto, as may be amended from time to time. 

Additionally, you shall be granted an option (the “Option”) to purchase an additional 90,000 shares of the Company’s stock. The shares will be
at an exercise price equal to the fair market value of such shares on the date of grant as determined by the Company’s Board of Directors. The Option shall be granted pursuant to and upon the terms set forth in the Company’s stock
incentive plan and your stock option agreement and shall have a maximum term of 10 years (subject to earlier termination in connection with a termination of your employment or a change in control of the Company). So long as you remain actively
employed by the Company, the Option shall vest on January 31st of each year beginning in 2015 with respect to your achievement of new bookings and customer retention objectives for the
immediately prior fiscal year based on the board approved operating plan for such year (the “Plan”) as follows: (i) 25% of the underlying options if actual new bookings and customer retention in the prior fiscal year
(“performance”) equal or exceed 100% of the Plan; or (ii) 12.5% if performance equals or exceeds 90% of the Plan; or (iii) 0% if performance is less than 90% of the Plan. As described, you will be eligible to vest a maximum of
25% of the underlying options annually based on performance in each calendar year beginning in 2014 and ending in 2017. Any options not vested pursuant to the vesting terms described above for a particular calendar year shall be forfeited and
achievement against the applicable Plan shall be as determined by the Board in its sole discretion. 
 You will be entitled to the Company’s double
trigger acceleration of vesting on the options outlined above in the event of a change of control as approved by the board of directors and applicable to all employees. 

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 this offer, please sign and return this letter to me. This offer will expire at 5:00 pm Pacific Time on Tuesday, September 10, 2013, if not
accepted before then. 
 [Remainder of page intentionally left blank] 

 We look forward to working with you at the Company. 

If you have any questions, please call me at [Telephone]. 
  

	
	Sincerely,
	
	 /s/ Shannon Espinola

	Shannon Espinola
	Director, People Strategy

 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/ Michele K. Law
	 		 		 	
	Employee Signature	 		 		 	
				
	 Michele K. Law
	 		 	 September 10, 2013
	 	
	Printed Name	 		 	Date	 	
				
	 TBD
	 		 		 	
	Employment Start Date	 		 		 	

  

			
	Enclosures:	  	At-Will Employment, Confidential Information, Invention Assignment and Arbitration AgreementEX-10.8

 Exhibit 10.8 

JOB OFFER LETTER 
 September 28, 2010

 Randy Womack 
 [Address] 

Dear Randy: 
 On behalf of Castlight, Inc., a
Delaware corporation (the “Company”), I am pleased to offer you, conditional on satisfactory results of a routine background check, and other matters mentioned below, the position of Chief Operating Officer at a starting salary of $250,000
per year, subject to applicable withholdings and deductions, payable in accordance with the Company’s standard payroll schedule and procedures. Commencing with calendar year 2011, you will also be eligible for a year-end bonus of up to 60% of
your base salary for such year, payable to the extent you achieve milestones that will be determined by the Company’s Board of Directors. If you accept this offer, we expect that your start date will be 11/08/10. Your primary duties will be to
plan and scale all internal operations of the Company. Of course, the Company may modify your responsibilities and compensation from time to time, as it deems necessary. 

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. 

Subject to the approval of the Company’s Board of Directors, you shall be granted an option (the “Option”) to purchase
1,264,864 shares of the Company’s common stock, at an exercise price equal to the fair market value of such shares on the date of grant as determined by the Company’s Board of Directors. The Option shall be granted pursuant to and upon the
terms set forth in the Company’s stock incentive plan and your stock option agreement and shall have a maximum term of 10 years (subject to earlier termination in connection with a termination of your employment or a change in control of the
Company). So long as you remain actively employed by the Company, the Option shall vest with respect to 25% of the underlying shares on the one-year anniversary of your employment start date and, with respect to the balance, in 36 substantially
equal installments upon your completion of each additional consecutive month of service thereafter. 
 Additionally, subject to the approval
of the Company’s Board of Directors, you shall be granted a milestone based option (the “Milestone Option”) to purchase 158,108 shares of the Company’s common stock, at an exercise price equal to the fair market value of such
shares on the date of grant as determined by the Company’s Board of Directors. The Milestone Option shall be granted pursuant to and upon the terms set forth in the Company’s stock incentive plan

 
and your Milestone Option stock option agreement and shall have a maximum term of 10 years (subject to earlier termination in connection with a termination of your employment or a change in
control of the Company). So long as you remain actively employed by the Company, the Milestone Option shall vest as to a certain number of shares upon the attainment of milestones as determined by the Board and as set forth in the Milestone Option
stock option agreement 
 Among other terms and conditions set forth in the Company’s stock incentive plan and your stock option
agreements, the shares underlying the Option and the Milestone Option will be subject to rights of first refusal and a market standoff agreement, and your exercise of the Option and the Milestone Option are conditioned upon your execution of the
Amended and Restated Voting Agreement, dated August 21, 2009, by and among the Company and the parties thereto, as may be amended from time to time, and the Amended and Restated Right of First Refusal and Co-Sale Agreement, dated
August 21, 2009, by and among the Company and the parties thereto, as may be amended from time to time. 
 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. A duplicate original of this offer is enclosed for your records. To accept this offer, please sign and return this letter to me. 

[Remainder of page intentionally left blank] 

  
 2 

 We look forward to working with you at the Company. 

If you have any questions, please call me at [Telephone]. 
  

	
	Sincerely,
	
	 /s/ Giovanni Colella

	Giovanni Colella
	Chief Executive Officer

 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/ Randy Womack
	 		 		 	
	Employee Signature	 		 		 	
				
	 Randy Womack
	 		 	 September 29, 2010
	 	
	Printed Name	 		 	Date:	 	

  

			
	Enclosures:	  	 Duplicate Original Letter
 At-Will
Employment, Confidential Information, Invention Assignment and Arbitration Agreement

  
 3

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