Investor Overview
March 7, 2017
2
Safe Harbor
Statement
This presentation contains forward-looking statements regarding our
trends, our strategies and the anticipated performance of our business,
including our guidance for the full year of 2017. These statements are
made as of today, and reflect management’s current views and
expectations, and are subject to various risks, uncertainties and
assumptions. If this presentation is viewed after today, the information in
the presentation may no longer be current or accurate. We disclaim any
obligation to update or revise any forward-looking statements.
Please refer to the Company’s fourth quarter and full year 2017 financial
results press release dated February 15, 2017, and the risk factors
included in the company’s filings with the Securities and Exchange
Commission for discussion of important factors that may cause actual
events or results to differ materially from those contained in our forward-
looking statements.
The guidance provided in this presentation was made on February 15,
2017. The Company does not update its guidance intra-quarter through
investor presentations such as this.
This presentation also includes certain non-GAAP metrics, such as non-
GAAP gross margin, operating expenses, and operating loss, that we
believe aid in the understanding of our financial results. A reconciliation to
comparable GAAP metrics, on a historical basis, can be found in the
appendix section of this presentation.
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Legend
IMPORTANT ADDITIONAL INFORMATION WILL BE FILED WITH THE SEC
In connection with the proposed transaction between Castlight and Jiff, Castlight has filed a
registration statement on Form S-4 with the SEC (Registration Statement No. 333-215861), and
this registration statement, as amended, was declared effective by the SEC on February 14,
2017. This registration statement contains a joint proxy statement/prospectus/information
statement and relevant materials concerning the proposed transaction. Castlight and Jiff mailed
the definitive joint proxy statement/prospectus/information statement to their respective
stockholders on February 24, 2017. Additionally, Castlight intends to file with the SEC other
relevant materials in connection with the proposed transaction. STOCKHOLDERS OF
CASTLIGHT 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 SEC’s web site,
http://www.sec.gov. Documents will also be available for free from Castlight 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.
Castlight and its executive officers and directors may be deemed to be participants in the
solicitation of proxies from Castlight’s stockholders with respect of 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 Castlight, Jiff or any of the executive officers
or directors of Castlight or Jiff may have in the proposed transaction with Jiff is included in the
joint proxy statement/prospectus/information statement that Castlight has filed with the SEC in
connection with its stockholder vote on matters relating to the proposed transaction. Information
about the directors and executive officers of Castlight, including their respective interest in
security holding of Castlight, is set forth in the proxy statement for Castlight’s 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.
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Castlight is a health benefits platform that engages employees
to make better health decisions and enables benefit leaders to
communicate and measure their programs
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Health Benefits
Today: low
engagement & poor
health decisions
73% of employees don’t fully
understand their health benefits
Program utilization is typically lower
than 10%
Employees pay up to 10X more for the
same service
Up to 20% of surgeries are
unnecessary
5-6% increase in health spending
each year for employers
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Why aren’t employees engaged?
Explosion
of vendors
Soaring consumer
expectations
Convoluted
healthcare system
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All-in-one wellbeing
Deep partner integrations
Motivating user experience
1
2
3
Comprehensive decision support
Data-driven personalization
Multi-channel outreach
1
2
3
Health
Benefits
Platform
For employees
Improve every aspect of their health experience: from staying healthy,
to accessing care, to managing a condition
For employers
More efficient than ever before to engage with employees, purchase
and deploy a wide range of benefit technologies, and measure impact
The Solution: One End-to-End Platform
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The Castlight Health Benefits Platform
Integrate Engage Evaluate
Targeted, timely
communications to
GUIDE employees to
better decisions
Simple, integrated way to
help UNDERSTAND &
ACCESS benefits
Real-time INSIGHT into
engagement with
benefits and programs
One end-to-end platform
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Integrate
Across medical, pharmacy, dental, behavioral
health and third party programs
Picking a doctor
Deciding where to get urgent care
Getting the most out a benefits plan
Learning how to manage a chronic condition
Example Decision Areas
Cost
Personalized cost
estimates for the
employee based on their
specific plan design,
network, and amount
spent to date
Education Content
Consumer-oriented content, written by
expert clinicians, that supports
procedures, conditions, vaccines, labs,
imaging, and more
Quality
17 nationally endorsed
sources of clinical
quality for hospitals and
physicians, including
condition and procedure
specific information
Tracking finances (e.g. HSA spend, claims)
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Engage
Personalized employee experience based on their health journey
Predict Health
Risk
Claims, demographics, and
employee activity data drive
identification of employee
health status and potential
future health conditions
Recommend Best
Options
Individualized presentation
of services and programs
drives the employee to the
right care and program at
the right time
Multi-Channel
Outreach
Proactive connection with
employees where they are,
via the channels most
applicable to them
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Evaluate
Back Pain Diabetes Adult Preventative
Care
Start PT
or chiropractic care Take a glucose test
Complete a preventive
service
Individuals with lower
back pain
(who aren’t using PT or
chiropractic care)
Individuals with or at
risk for diabetes
(who have not had
a glucose test)
Adults who have not
had a preventive
service within one year
About the
Campaign
Campaign
Recommendation
Impact on
Preventive
Services
2.7x
increase
1.8x
increase
1.7x
increase
Note: Early results from claims-based analysis aggregated from customers that have been deployed on Castlight Action for over 6 months
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The Jiff Wellbeing
Platform
Central hub for wellbeing that drives
employee engagement
App store approach integrates with over
50+ solutions that sync seamlessly
Mobile-first technology with a world-
class user experience
Model: PEPM-based subscription and
service fees, contract terms typically
three-years paid monthly, quarterly or
annually
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Jiff’s Motivating User Experience
Personalized incentives
Rewards tied to specific micro-behaviors
that meet users where they are.
Game mechanics
Principles from online games and behavior
science that make products stickier.
Everyday engagement
Engage the user every day with
opportunities to stay healthy or improve
health.
Mobile-first design
A consumer grade product that is always in
your pocket, and easy to use.
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Jiff’s Ecosystem & Deep Partner Integrations
Incentivize specific
targeted behavior deep
within third party
solutions
Collect ‘digital exhaust’
on users for
personalization and
reporting
Scalable
Integration
Framework
Bi-directional
flow of data
Purchase a wide range
of solutions directly thru
Jiff
Reseller
Contracts
Activity Tracking
Food Tracking
Sleep Tracking
Fitness Tracking
Biometrics
HRA
Health Coaching
Nutritional Coaching
Resilience
Smoking Cessation
Fertility / Pregnancy
Parenting
Cardiovascular
Health
Financial Health
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Joint Value Proposition
Engage employees with
comprehensive wellbeing offering
Interact with employees
throughout the year
Target most expensive
conditions and employees
Personalize incentives and
deploy latest digital therapeutics
Increase employee happiness
while decreasing risk
Improve efficiency of the health
care system and quality of care
Lower costs for and
employer’s most
expensive population
Manage
Conditions
Real time intercept when your
employee is about to become a patient
Market-leading healthcare decision
support, built in
Simplify navigation for all benefit resources, globally
Stay
Healthy
Access
Care
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The Power of the Castlight-Jiff Combination
Most Comprehensive
Health Benefits
Platform
• Addresses total employee
population spanning
wellbeing (Jiff) and
decision support (CSLT)
• Strong differentiation
across product breadth,
data, personalization, and
ecosystem partnerships
• Complementary strengths
in channel partnerships
Accelerated Growth
Profile
• Expected 2017 pro forma
non-GAAP revenue:
• $138-$142 million for
the combined business
• Combined business
growth of 27%-30%
(vs. 21% for CSLT
standalone)
Increased Scale
• Combined business
creates a clear path to
larger scale, faster growth
• Cost efficiencies driven by
highly complementary
business models
Financial Update
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Executed on key priorities in 2016
Ramped
adoption of our
platform offering Set foundation for
long-term growth
Drove the business
towards cash flow
breakeven
2016 execution provides a strong start to 2017
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Financial Highlights
STRONG GROWTH
HEALTHY MARGIN
PROFILE
SCALING
BUSINESS
$102M IN 2016
REVENUE
75% Q4 2016 GROSS
MARGINS
90% REDUCTION IN
Y/Y OPERATING
LOSS IN 4Q 2016
$75 $102
2015 2016
35% Growth
59%
75%
4Q '15 4Q'16
-$14.9
-$1.5
4Q'15 4Q'16
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Strong Balance Sheet
Non-GAAP figures adjusted for Stock Based Comp, Capitalization and Amortization of Software, Litigation Settlement,
charges related to reduction in force and acquisition related costs
Cash at End of
Q4 2016
Q4 2016 Cash
Used in Operations
$114.6 M ($1.7 M)
CSLT/Jiff: CASH FLOW BREAKEVEN BY YEAR-END 2018
On a stand-alone basis, Castlight expects to reach cash flow breakeven
by mid-2017
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Standalone Pro Forma
• Standalone revenue of $123M at the high-end
• Non-GAAP operating loss of approximately
$9M to $11M
• Non-GAAP net loss per share of $0.08 to $0.10
based on approximately 107M to 108M shares
Combined Pro Forma
• 2017 non-GAAP rev. range: $138M to $142M*
• Assumptions at the high-end of the range:
• Castlight at $123M
• Jiff at $19M
• 27%-30% year-over-year growth
• Expect to reach cash flow breakeven by the
end of 2018 with a cash balance of $60M or
greater
* Assumes a full year of revenue contribution from Jiff and
no impact from purchase accounting adjustments
associated with purchase accounting for GAAP purposes.
Guidance
Castlight plans to provide GAAP revenue guidance for the combined
company when it announces financial results for the first quarter of 2017
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2017 Key Priorities: Focus on Growth
2017 Initiatives
Drive faster adoption
of our platform
offering by new
customers
Drive customer
stickiness and long
term success
Integrate Castlight
and Jiff to unlock the
strategic value of our
combined company
Investor Overview
March 2017
Appendix
March 2017
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Castlight’s
Business Model &
Go-To-Market
Business Model
• Platform sold on a price per employee per
month (PEPM) basis
• Typically three-year contracts
• Long-term gross margin target range of 70%-
75%
Target Customers
• Targets US self-insured employers
• Platform purchased by health benefits
manager/HR
• 211 customers, including 60+ Fortune 500
Go-To-Market
• Direct sales team/channel partner approach
• Strategic relationships with Anthem and SAP
• Expanding relationships with health benefits
consultants
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Jiff Transaction
Terms
Consideration
Castlight to issue approximately 27M shares and options
Earnout
• Issuance of up to 4M shares issuable upon achievement of specific
growth objectives for the Jiff business in FY 2017
• 3M additional shares upon Jiff achieving $25M in net new bookings
• 1M additional shares upon Jiff achieving $25M in GAAP revenue
Pro Forma Ownership
Castlight shareholders to own ~80% of Company and Jiff shareholders to
own ~20% of the combined company on a fully-diluted basis
Pro Forma Ownership
• John Doyle to become CEO of combined company
• Derek Newell to become President of combined company
• Giovanni Colella will continue in role of executive chairman
• Two members of current Jiff board will be appointed to Castlight board
Closing Conditions
• Subject to satisfaction of customary closing conditions, including
approval from Castlight’s stockholders with respect to the issuance of
Castlight shares in the transaction
• Expected to close at the end of 1Q 2017
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Gross Profit: Reconciliation of GAAP to Non-GAAP
Three Months Ended
December 31, March 31, June 30, September 30, December 31,
2015 2016 2016 2016 2016
Gross profit:
GAAP gross profit subscription 16,048$ 16,901$ 17,861$ 19,879$ 23,912$
Stock-based compensation 87 108 120 139 139
Amortization of internal-use software 124 244 244 244 244
Reduction in workforce - - 5 - -
Non-GAAP gross profit subscription 16,259$ 17,253$ 18,230$ 20,262$ 24,295$
GAAP gross margin subscription 80.5% 80.3% 81.4% 83.3% 84.9%
Non-GAAP gross margin subscription 81.6% 81.9% 83.0% 84.9% 86.3%
GAAP gross loss professional services (4,388)$ (3,433)$ (3,220)$ (2,344)$ (2,417)$
Stock-based compensation 653 477 535 456 493
Capitalization of internal-use software (30) - - - -
Reduction in workforce - - 99 4 -
Non-GAAP gross loss professional services (3,765)$ (2,956)$ (2,586)$ (1,884)$ (1,924)$
GAAP gross margin professional services (318)% (204)% (198)% (143)% (139)%
Non-GAAP gross margin professional services (272)% (176)% (159)% (115)% (111)%
GAAP gross profit 11,660$ 13,468$ 14,641$ 17,535$ 21,495$
Impact of non-GAAP adjustments 834 829 1,003 843 876
Non-GAAP gross profit 12,494$ 14,297$ 15,644$ 18,378$ 22,371$
GAAP gross margin 54.7% 59.3% 62.1% 68.8% 71.9%
Non-GAAP gross margin 58.6% 62.9% 66.3% 72.1% 74.8%
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Operating Expense: Reconciliation of GAAP to Non-GAAP
Three Months Ended
December 31, March 31, June 30, September 30, December 31,
2015 2016 2016 2016 2016
Operating expense:
GAAP sales and marketing 16,579$ 16,282$ 15,452$ 13,143$ 13,923$
Stock-based compensation (1,822) (2,235) (2,219) (2,190) (2,199)
Reduction in workforce - - (374) (48) -
Non-GAAP sales and marketing 14,757$ 14,047$ 12,859$ 10,905$ 11,724$
GAAP research and development 8,224$ 10,085$ 9,961$ 10,573$ 9,841$
Stock-based compensation (1,154) (1,405) (1,264) (1,631) (1,659)
Capitalization of internal-use software 620 - - - -
Reduction in workforce - - (118) (18) -
Non-GAAP research and development 7,690$ 8,680$ 8,579$ 8,924$ 8,182$
GAAP general and administrative 5,983$ 8,545$ 6,019$ 5,338$ 6,957$
Stock-based compensation (1,069) (1,269) (971) (1,236) (1,267)
Litigation settlement - (2,735) (141) - -
Reduction in workforce - - (80) (10) -
Acquisition expenses - - - - (1,731)
Non-GAAP general and administrative 4,914$ 4,541$ 4,827$ 4,092$ 3,959$
GAAP operating expense 30,786$ 34,912$ 31,432$ 29,054$ 30,721$
Impact of non-GAAP adjustments (3,425) (7,644) (5,167) (5,133) (6,856)
Non-GAAP operating expense 27,361$ 27,268$ 26,265$ 23,921$ 23,865$
Operating loss:
GAAP operating loss (19,126)$ (21,444)$ (16,791)$ (11,519)$ (9,226)$
Impact of non-GAAP adjustments 4,259 8,473 6,170 5,976 7,732
Non-GAAP operating loss (14,867)$ (12,971)$ (10,621)$ (5,543)$ (1,494)$