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Castlight Health

Investor P resentation

J une 2020

(NY S E : C S L T )

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S afe Harbor S tatementThis presentation contains forward-looking statements within the meaning of the “safe harbor” provisions of the Private SecuritiesLitigation Reform Act of 1995 including, but not limited to, our trends, our strategies and the anticipated performance of ourbusiness, our guidance for the second half and full year of 2020, the current and future impacts of C O VID-19 on our business,actions we have taken in response to C O VID-19, our long-term outlook, expected AR R growth, our license agreement andrelationship with Anthem, our executive leadership, cost savings efforts, impact of non-renewals, sales momentum and expectedtiming of sales cycles, future churn risk and future cash position. Forward-looking statements are subject to risks anduncertainties that may cause our actual activities or results to differ significantly from those expressed in any forward-lookingstatement, including risks set forth in our filings with the Securities and Exchange Commission. Statements contained herein aremade as of or for the first fiscal quarter ended March 31, 2020. The information in the presentation is provided to you as of thedates indicated and we do not intend to update the information after its distribution, even in the event that the informationbecomes materially inaccurate, unless required by law.

The guidance provided in this presentation is based on the statements made as of May 7, 2020 in connection with the release ofour earnings results for the quarter ended March 31, 2020 and reflect management’s views and expectations at that time. We arenot reaffirming or providing any further guidance or updates on our performance now. Please refer to the risk factors included inour filings with the Securities and Exchange Commission for discussion of important factors that may cause actual events orresults to differ materially from those contained in our forward-looking statements, including in our Form 10-Q for the quarterended March 31, 2020.

Non-G A A P Financ ial Meas uresTo supplement Castlight Health’s financial statements presented in accordance with generally accepted accounting principles (GAAP), wealso use and provide investors and others with non-GAAP measures of certain components of financial performance, including non-GAAPgross profit and margin, non-GAAP operating expense, non-GAAP operating loss, non-GAAP net loss and non-GAAP net loss per share.Non-GAAP gross profit and margin, non-GAAP operating expense, non-GAAP operating loss, and non-GAAP net loss exclude stock-basedcompensation, goodwill impairment, certain legal expenses, amortization of intangibles, capitalization and amortization of internal-usesoftware, and lease exit and related charges.

We believe that these non-GAAP financial measures provide useful supplemental information to investors and others, facilitate the analysisof the company’s core operating results and comparison of operating results across reporting periods, and can help enhance overallunderstanding of the company’s historical financial performance.

These non-GAAP financial measures should be considered in addition to, not as a substitute for or in isolation from, measures prepared inaccordance with GAAP. Further, these non-GAAP measures may differ from the non-GAAP information used by other companies, includingpeer companies, and therefore comparability may be limited. Castlight Health encourages investors and others to review the company’sfinancial information in its entirety and not rely on a single financial measure. We have provided a reconciliation of these non-GAAPfinancial measures to the most directly comparable GAAP measures, which is available in the appendix.

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Investment Highlights

A leading prov ider of health nav ig ation s olutions to employers and health plans

Operating in a larg e and growing market driven by consumer adoption of digital healthcare and need for navigation solutions

Launching new produc t offering s to ex pand market opportunity and better support customers and members (C are Guides )

Multiple way s to grow

New manag ement team bridges outside healthcare expertise with company experience

E xpect to approach cas h flow breakeven during 2H’2020

• E mployers

• Health plans • C O VID -19 related

• New solutions

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Castlight at a Glance

Founded

Employees

Total Addressable Market

Fortune 500 Companies

Lives on the Platform

Invested in the Platform

Records in Data Asset

Revenue FY2019

Our health navigation platform connects hundreds of health vendors , benefits resources , and plan des igns into one comprehensive health and wellbeing experience. We guide individuals —based on their unique profile—to the best res ources available to them, whether they are healthy, chronically ill, or actively seeking medical care. C astlight transforms the employee benefit experience into a deeply personalized, yet simple, guided one, empowering better-informed patient decis ions to unlock better healthcare outcomes and maximiz ing return on healthcare investments.

2008

400+

60+

~20M

$300+

3B +

$143M

$8B +

5

Senior Management combines company +

healthcare experience

NameY ears at

C S L TP rev ious E x perienc e

Maev e O’Meara C hief E xecutive Officer 10

Will B ondurantC hief F inancial Officer 7

K eith R eynoldsC hief C ommercial Officer <1

Matt MoranS VP of C orporate

Development<1

J ay es h P atel S VP , Product and User

E xperience 9

A ng el R os aS VP , C ustomer E xperience <1

6

A decade of innovation

S ingle ex perienc e for the complete

health journey

TO D A Y

2010

Hig h-T ouc h (C are Guides )

Omni-channel approach, with empathic humanconcierge guides and proactive outreach to users with identifiedgaps in car

P ers onalization

Predictive analytics , machine learning/AI based models , omni-channel, real time recommendations

Wellbeing

Challenges , content, mind/ body/wallet, global, social, incentives , coaching, screening

E c os ys tem

Platform integration framework to enable rapid data sharing and user experience integration of best in breed partners

B ehav ioral Health

Guides employees to cost-efficient, effective, access ible behavioral health care

Trans parenc y

Medical, Rx, dentalcomparison, spendmanagement, provider quality, network strategy,care planning tools

2015 2017 2018 20192016

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Strategic Priorities Update

R ev italize direc t-to-employ er bus ines s

B road launc h Cas tlig ht Care G uides

Health plan growth s trateg y

Optimize operating profile

2020 P riorities

Hired ex perienc ed Commerc ial leaders hip

R eturn to innov ation with Cas tlig ht Care G uides

R enewed and s treng thened A nthem partners hip

Unified all s olutions to a s ing le tec h s tac k

2019 A c c omplis hments

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Health Benefits are Challenging to Navigate

NutritionP rog ram

E A P

Maternity Manag ement

Health Conc ierg e

B enefit

Condition Manag ement

P rog ram

Mental Wellbeing P rog ram

Cos t & quality trans parenc y

Health S av ing s A c c ount

F inanc ial Wellbeing

HealthB enefits?? ?

What doc tor do I choos e?

?

How can I improve my lifes ty le behav iors ?

?

How can I s av e money

on healthc are?

?

How do I know what benefits are available to me?

?

How can I get help with my condition?

?

Where s hould I go for my care?

?

Can I afford my care?

?

How can I manag e s tres s better?

?

73% of employees don't understand their

health benefits

70% prefer digital over in-person for a

portion of their healthcare solutions

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Castlight Complete Solution

Care

Guidance

Navigator

Castlight Care Guidance empowers employees to make better healthcare decis ions , demystify available benefits, and engage in the right programs at the right time.

• Guide to the bes t care option• Clarity of prov ider cos t and clinic al quality• R educ e overall medic al spend

Wellbeing

Navigator

Comprehens iv e health nav ig ation helps employees manage health, whether they are healthy, managing a condition or actively seeking medical care. Improved health = savings for employee and employer.• One central hub for all health benefits • Data-driven, personalized user experience• Highly configurable and company-s pecific

Wellbeing Navigator engages entire employee populations to our E cos ystem of enterprise vendors you already offer, best-of-breed partners , and apps and wearables employees use every day.

• Claims -driven pers onalization• S us tain employ ee eng ag ement• Deep integ ration for a seamles s ex perienc e

S ingle experience

for the complete

health journey

R ev italize direct-to-employ er bus ines s

1010

Powered by Data Aggregation & Integration

at Scale

34 Medical payors10 Pharmacy Benefit Managers (P B Ms)16 Dental payors15 Behavioral / E AP programs

113 E ligibility Vendors 60 Bank integrations

100+ distinct AP I integrations150+ distinct single sign-on (S S O ) integrations

AI and machine learningS ingle stack architecture

E c os y s tem Vendor

Medic al Pay ors

PB MsDental Pay ors

Cons umer Trac kers

E nrollment Vendors

Cus tomer Vendors

Us er B ehav ior

HS A vendors

Medical ClaimsProvider DirectoryUnit PricesNarrow Networks AccumulatorsBenefit Des ignIns urance card

Pharmacy ClaimsFormulariesPreventive Drug ListsPharmacy NetworksAdherence AlertsIns urance cardAccumulators

Dental ClaimsDental DirectoryPricesAnnual Accumulator Ortho Accumulator

Program Actions completedProgram completionKey results and outcomes (e.g ., biometrics , HS A balance)

Fitness , sleep, or nutrition data

Member E ligibility information (social, demographic, human info) E mbedded registration enrollment integration

Program Actions completedProgram completionKey results and outcomes

S earch Pulse S urveysGoal selectorHealth Assess ment

Account BalancesS S O

3B+data points

| 1111

E lig ibility file data(s oc ial,

demog raphic s )

Medic al & R x Claims

B iometric s & Health R is k As s es s ment

Health Goals

S earc h, Pag e Views , Etc .

Ingest DataAI/Machine Learning

Models Applied

Over 116 S eg ments

Across 35 Categ ories in both Clinical Conditions and Health & Wellbeing

S ourced from Claims, S earch History, E -file, Health Assessment, Health Goals , IBM Watson and Biometrics results

Prioritize and S egment Users

so they receive campaigns with the most relevant, timely mes s ag ing and content, based on their segmentation.

In App R ec ommendation

sTarg eted

E mails

Data Asset Drives Personalization

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Recommendations drive engagement with

pre-integrated ecosystem vendors

* Limited integration available

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R ev italize direct-to-employ er bus ines s

Pers onalized home pag e provides key information and promotes relevant programs ,

benefits and services to the user

Provider searc h res ults unique to us er, incorporating proprietary

clinical quality score, cost, and the user’s health profile

Machine-learning bas ed pers onalization rec ommends relevant benefits or “next best

action” to the user, updated daily

Integration with dozens of ec os ys tem vendors to power

health improvement and corporate wellnes s programs

Castlight Complete Solution

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Castlight Care Guides

• Offers one-to-one live support to connect employees to the right benefits and care

• E ngages users through their preferred modality—chat, telephone, or email

• S teers employees to the best next step in their healthcare journey

• S calable and fully integrated service built on top of Castlight’s exis ting personalized data platform

Recent Accomplishments

• Completed S alt Lake City Customer Center of E xcellence

• Launched initial customer, a large manufacturer

• Quickly developed Care G uides support for customers and users impacted by COV ID -19, with focus on vulnerable populations

F requent Use Cases

• Am I being overcharged?

• How do I pay for my specialty drug?

• How do I best manage my chronic condition?

R outed to the appropriate

team member

• S upport

• Clinical

• Nursing

B roadly launc h Cas tlig ht Care Guides

High-touch, human service leveraging Castlight’spersonalization engine to efficiently deliver ass istance

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Health plan growth strateg yHealth Plan Strategy Expands

Market Opportunity

• S igned October 2019, effective J anuary 1st, 2020

• $168M total contract value, 30-month agreement

• E xpands relationship (~20% increase in AR R vs AR R at end of Q3 2019)

• P roducts include white-labeled health navigation solution for large employers and embedded navigation services for Anthem’s full commercial membership

• P roof point for health plan market

R enewed & E x panded A nthem R elations hip

• Approximately 100 health plans worth pursuing (>150m covered members)

• National plans , Blue Cross Blue S hield plans , and regional health plans

• Hired health plan sales team in Q3 2019, with leader who succes sfully sold technology to multiple health plans

• E xpect 12 to 18-month sales cycles ; 2020 goal to sign a second plan (in addition to Anthem)

• Offerings include white-labeled full navigation platform, embedded transparency, personalization services , and clinical quality.

• White-label plus ability to embed functionality into a plan’s user experience allows us to meet the health plan where they are on their technology journey

Unloc k ing Health P lans as G rowth Vec tor+

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COVID response demonstrates innovative thinking,

nimble execution, and ability to partner

Tes t S ite F inder

R is k Heat Maps

Geographic distribution of populations at greatest risk of severe disease with COVID -19 infection and limited access to intens ive care

• R eacted quickly and nimbly to support our team members, customers, and users

• Identified areas where Castlight solutions could be utilized to addres s the cris is and provide value to customers & Americans

• Launched Working Well product to support employers in return-to-workplace and navigation in new world

COVID -19 R es pons e

• Multiple S tate Health Departments (e.g., S tate of NY, MI, NC, etc.) embedding test site finder

• Big tech (e.g., Google) utilizing data to power COVID information in search & maps

• P BM & R etailers using data to inform COVID initiatives (e.g., tes t site locations)

P owering New P artners

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Medic al S pend R educ ed

~2% for low-risk members

~7% for high-risk members

Engagement Produces Results

2-3x R O I

Engage and Delight

o P latform eng ag ement: Complete had a 61 percent subscriber registration rate and a 38 percent monthly return rate in 2019, exceeding engagement rates of typical health apps that show an average retention rate of just 15 percent after only 30 days

o E mployee ex perienc e: The Castlight Complete mobile app has a Net Promoter S core (NP S ) of 75, in addition to a 4.7 App S tore rating across 2019, outperforming the average mobile app NP S of 30

Drive Behavior Change

o A ppropriate care: 38 percent of registered Castlight users had a preventive office vis it over 2019 compared with only 25 percent of non-users .

o Hig h-value prov ider: E mployees using Complete received care in an emergency room 25 percent less often than non-users after being directed to more appropriate care options . Through Castlight's proprietary quality scoring, we match employees with high-quality providers , resulting in 15 percent fewer inpatient days per year. Additionally, Castlight has reduced medical spending, including approximately 12 percent reduction in labs and imaging costs for those who search for care within the Castlight app.

o P rog ram utilization: Complete achieved 1.4 to 2.4 times higher engagement in employer-offered health and wellness solutions that are integrated into the Complete platform.

1

1 S pend reduction for Castlight Complete users utilizing both Care Guidance and Wellnes s features ; excludes high-cost outliers (members with more than $75k in annual medical claims cost incurred)

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“We wanted one message, one platform, one plac e to go. It worked:

by 6 months we had 88% registration with a 90% return rate.”

GE Appliances focused on one simple, meaningful incentive to launch Castlight to their salaried

employees who elected Health R eimbursement Accounts (HR A). All adult health plan members were

required to register for the program in order to receive HR A dollars .

Building on 2019 success , GE Appliances added to their Castlight experience in 2020

with comprehens ive wellbeing and enhanced personalization for employees .

• One-stop platform for all health benefits and services

• Increase member awareness and engagement with available resources

• One cons istent, constantly repeated, omnichannel communication campaign

• 100% of HR A account funding at risk pending registration of all adult health plan members

• E mbed program registration in workflows of ons ite healthcare teams and Anthem member touches

Goals Strategies Results

61% viewed a benefit program

89% opened a personalized

communication

75 Net Promoter S core

88% of targeted population registered

in the first 6 months

90% of registered users have

returned to the Castlight platform

Case Study

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Financial Overview

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Financial Highlights

• P MP M-bas ed bus iness model selling to employers and health plans

• Highly vis ible and recurring revenue

• Multi-year, non-cancellable contracts

• F avorable S aaS -bas ed gros s margin profile

• Sta ble balance sheet, after cost structure measures in 1Q20

• E xpect to approach cash flow breakeven during 2H’20, expect to end 2020 with around $40m of cash

(1) 2020 Cash Outlook based on 2020 Q1 Results Press Release, dated May 7 th 2020

(1)

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1Q’20 Results

$35.5

$39.0

1Q19 1Q20

R evenue

63.3%65.1%

1Q19 1Q20

Non-G AAP G ross Margin

-$5.3

-$2.2

1Q19 1Q20

Non-G AAP Operating Los s

A nnualized R ec urring R ev enue (A R R )

• $142.4 million as of 3/31/20

• 3% sequential decline, reflecting churn and a couple of deals that did not close in 1Q20 but which continue contracting

• 75%+ of total AR R is on Castlight Complete or Anthem

Optimize operating profile

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Diverse Customer Base with Durable Revenue Model

Financial Highlights

• High-recurring P MP M-based bus iness model

• Multi-year contracts

• F avorable S aaS -based gross margin profile

$229 Million of non-canc ellable bac k log (1)

(1) As of March 31, 2020

27%

23%

11%

10%

8%

6%

15%

Telecomm

ManufacturingHealthcare

Finance

R etail

Consumer P ackaged

Goods

Other

1Q20 A R R by Indus try

23

$44 million

Cash Metrics

Cas h* as of Marc h 31, 2020

A pproac h cas h-flow breakev en

2H 2020 Outlook

* Cash, cash equivalents and marketable securities

E x pec t to end 2020 with around $40 million in cas h*

(1) Based on 2020 Q1 Results Press Release, dated May 7th 2020

(1)

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2020 Outlook

G AAP R evenue $127mm – $135mm

Non-G AAP Operating Income/(L os s )

($17)mm – ($24)mm

Non-G AAP E P S ($0.11) – ($0.16)

Weighted Avg. S hares Outstanding

150mm – 151mm

Cash Used in Operations ($12)mm – ($20)mm

(1) 2020 Outlook based on 2020 Q1 Results Press Release, dated May 7 th 2020

(1)

2525

Appendix

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GAAP to Non-GAAP Reconciliation: Gross profit

Three Months Ended

March 31, 2020 December 31, 2019 March 31, 2019

Gross profit:

GAAP gross profit subscription $ 28,151 $ 25,573 $ 25,640

Stock-based compensation 169 179 219

Amortization of internal-use software 26 — —

Amortization of intangibles 530 530 587

Non-GAAP gross profit subscription $ 28,876 $ 26,282 $ 26,446

GAAP gross margin subscription 73.3 % 73.6 % 75.8 %

Non-GAAP gross margin subscription 75.2 % 75.7 % 78.2 %

GAAP gross loss professional services $ (3,579) $ (5,426) $ (4,260)

Stock-based compensation 116 216 265

Non-GAAP gross loss professional services $ (3,463) $ (5,210) $ (3,995)

GAAP gross margin professional services (541) % (315) % (253) %

Non-GAAP gross margin professional services (523) % (302) % (237) %

GAAP gross profit $ 24,572 $ 20,147 $ 21,380

Impact of non-GAAP adjustments 841 925 1,071

Non-GAAP gross profit $ 25,413 $ 21,072 $ 22,451

GAAP gross margin 62.9 % 55.3 % 60.2 %

Non-GAAP gross margin 65.1 % 57.8 % 63.3 %

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GAAP to Non-GAAP Reconciliation:

Operating ExpenseThree Months Ended

March 31, 2020 December 31, 2019 March 31, 2019

Operating expense:

GAAP sales and marketing $ 10,472 $ 10,664 $ 9,215

Stock-based compensation (672) (175) (627)

Amortization of intangibles (528) (529) (272)

Non-GAAP sales and marketing $ 9,272 $ 9,960 $ 8,316

GAAP research and development $ 13,822 $ 14,487 $ 15,725

Stock-based compensation (1,163) (1,369) (1,704)

Certain legal expenses 191 — (191)

Capitalization of internally developed software 21 80 —

Non-GAAP research and development $ 12,871 $ 13,198 $ 13,830

GAAP general and administrative $ 6,576 7,238 $ 7,293

Stock-based compensation (1,066) (1,217) (1,162)

Amortization of intangibles (17) (16) (17)

Certain legal expenses — — (533)

Non-GAAP general and administrative $ 5,493 $ 6,005 $ 5,581

GAAP goodwill impairment $ 50,300 $ — $ —

Goodwill impairment (50,300) — —

Non-GAAP goodwill impairment $ — $ — $ —

GAAP operating expense $ 81,170 $ 32,389 $ 32,233

Impact of non-GAAP adjustments (53,534) (3,226) (4,506)

Non-GAAP operating expense $ 27,636 $ 29,163 $ 27,727

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GAAP to Non-GAAP Reconciliation:

Operating loss

Three Months Ended

March 31, 2020 December 31, 2019 March 31, 2019

Operating loss:

GAAP operating loss $ (56,598) $ (12,242) $ (10,853)

Impact of non-GAAP adjustments 54,375 4,151 5,577

Non-GAAP operating loss $ (2,223) $ (8,091) $ (5,276)

Net loss and net loss per share:

GAAP net loss $ (56,335) $ (11,746) $ (10,539)

Total pre-tax impact of non-GAAP adjustments 54,375 4,151 5,577

Non-GAAP net loss $ (1,960) $ (7,595) $ (4,962)

GAAP net loss per share, basic and diluted $ (0.38) $ (0.08) $ (0.07)

Non-GAAP net loss per share, basic and diluted $ (0.01) $ (0.05) $ (0.03)

Shares used in basic and diluted net loss per share computation 148,872 147,359 143,000