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Castlight Health

Investor P resentation

S eptember 2020

(NY S E : C S L T )

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Safe Harbor

Statement

This presentation contains forward-looking statements about Castlight Health’sexpectations, plans, intentions, and strategies, including, but not limited to,statements regarding Castlight Health’s second quarter performance and 2020 fullyear projections, impact of C O VID-19, the success of our strategy and ourexpectations for our future business and financial performance. Statementsincluding words such as “anticipate,” “believe,” “estimate,” “will,” “continue,”“expect,” or “future,” and statements in the future tense are forward-lookingstatements. These forward-looking statements involve risks and uncertainties, aswell as assumptions, which, if they do not fully materialize or prove incorrect, couldcause our results to differ materially from those expressed or implied by suchforward-looking statements. The risks and uncertainties include those described inC a stlight Health’s documents filed with or furnished to the Securities and ExchangeCommission, including the risks set forth in our annual report on Form 10-K filed onFebruary 28, 2020, and our quarterly report on Form 10-Q for the three monthsended June 30, 2020, when filed. All forward-looking statements in this pressrelease are expressly qualified in their entirety by these cautionary statements andare based on information available to Castlight Health as of the date hereof.C astlight Health ass umes no obligation to update these forward-looking statements.

We provide guidance in this presentation, but we will not provide any furtherguidance or updates on our performance during the quarter unless we do so in apublic forum. Please refer to today’s press release and the risk factors included inthe company’s filings with the Securities and Exchange Commission for discussionof important factors that may cause actual events or results to differ materially fromthose contained in our forward-looking statements.

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

We believe that these non-GAAP financial measures provide useful supplemental information to investors and others, facilitatethe analysis of the company’s core operating results and comparison of operating results across reporting periods, and can helpenhance overall understanding of the company’s historical financial performance.

We have provided a reconciliation of each non-GAAP financial measure to the most directly comparable GAAP financialmeasure, except that we have not reconciled our non-GAAP operating loss and net loss per share guidance for the full year2020 to comparable GAAP measures because we do not provide guidance for stock-based compensation expense, andcapitalization and amortization of internal-use software, which are reconciling items between GAAP and non-GAAP. The factorsthat may impact our future stock-based compensation expense, and capitalization and amortization of internal-use software areout of our control and/or cannot be reasonably predicted, and therefore we are unable to provide such guidance withoutunreasonable effort. Factors include our market capitalization and related volatility of our stock price and our inability to projectthe cost or scope of internally produced software.

These non-GAAP financial measures should be considered in addition to, not as a substitute for or in isolation from, measuresprepared in accordance with GAAP.

Further, these non-GAAP measures may differ from the non-GAAP information used by other companies, including peercompanies, and therefore comparability may be limited. Castlight Health encourages investors and others to review thecompany’s financial information in its entirety and not rely on a single financial measure.

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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 hig h-touc h offering s to ex pand market opportunityand better support customers and members (C are Guides )

Multiple way s to grow

New manag ement team bridges outside healthcare expertise with company experience

Non-G A A P profit and pos itiv e cas h flow in 2Q’2020; expect to approach cash flow breakeven during 2H’2020

• E mployers

• Health plans • C O VID -19 related

• New solutions

5

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 +

6

Cigna Agreement Details

• S igned an ag reement with C ig na to serve their F ederal government and Taft-Hartley population

• Initial population is s ev eral hundred thous and F ederal G overnment employees out of C igna’s 6 million total

• Sta rts J anuary 1, 2021

• E x pec t A R R of ~$2 million*

* Not included in Q2’2020 AR R as the agreement was signed in Q3’2020 * Please see C astlight 8-K filed August 5th, 2020 for additional information

7

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

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

Tamar R udnic kS VP , Marketing 6

8

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

2020 P riorities

Health plan growth s trateg y

B road launc h of Cas tlig htCare G uides

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

Optimize operating profile

• Launched innovative return-to-work s olutions to support our customers

• S igned ag reement with Cig na • S trong mid/late-stage pipeline

• Three customers utiliz ing full Care Guides portfolio

• 30+ us ing free COVID -specific Care Guides support

• E stablishing financial sustainability• Non-G AAP profit and pos itive cas h

flow in Q2’2020

2Q 2020 Updates

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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

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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

| 1313

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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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

• Three cus tomers now utiliz ing full solution

• 30 customers us ing quickly developed Care G uides support for customers and us ers 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

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

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Health 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

• Met 2020 goal of signing a second plan with Cigna

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

• 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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Work ing WellT M Tes t S ite F inder

COVID-19 Support

• S trong pipeline of interest• S igned several customers worth $0.5mm annualized• Launched first customer J uly 2020

• Free solution for Castlight users and all Americans• S trengthening relationship with Google and more

than a dozen state & county health departments

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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 I1

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)

2020

“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

• Delivered pos itive cas h flow 2Q 2020 and expect to approach cas h flow breakeven during 2H 2020

• E xpect to end 2020 with around $40m of cas h

(1)

(1) Based on 2020 Q2 Results Press Release, dated July 28th 2020

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2Q 2020 Results

$35.9 $35.5

2Q19 2Q20

R evenue

65.1%

68.3%

2Q19 2Q20

Non-G AAP G ross Margin

-$2.2

$2.1

2Q19 2Q20

Non-G AAP Operating Income

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

• $139 million as of 6/30/20

• 2% sequential decline, reflecting a slowdown in employer contracting during the peak of COVID

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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

$199 Million of non-canc ellable bac k log (1)

(1) As of J une 30, 2020

27%

23%

11%

10%

8%

6%

15%

Telecomm

ManufacturingHealthcare

Finance

R etail

Consumer P ackaged

Goods

Other

25

$44 million

Cash Metrics

Cas h* as of J une 30, 2020

A pproac h cas h-flow breakev en

2H 2020 Outlook

* Cash, cash equivalents and marketable securities

Delivered pos itive cas h flow in 2Q 2020E x pec t to end 2020 with around $40 million in cas h*

(1) Based on 2020 Q2 Results Press Release, dated July 28th 2020

(1)

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2020 Outlook

(1) 2020 Outlook based on 2020 Q2 Results Press Release, dated July 28 th 2020

(1)

Metric R ang e

G AAP R evenue $127mm – $135mm

Non-G AAP Operating Loss ($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

E xpect to approach cashflow breakeven during 2H 2020

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Appendix

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GAAP to Non-GAAP Reconciliation: Gross profit

Three Months Ended Six Months Ended

June 30, 2020 March 31, 2020 June 30, 2019 June 30, 2020 June 30, 2019

Gross profit: GAAP gross profit subscription $ 25,470 $ 28,151 $ 25,730 $ 53,621 $ 51,370

Stock-based compensation 205 169 196 374 415 Amortization of internal-use software

79 26 — 105 — Amortization of intangibles 530 530 587 1,060 1,174 Reduction in workforce 221 — — 221 —

Non-GAAP gross profit subscription $ 26,505 $ 28,876 $ 26,513 $ 55,381 $ 52,959 GAAP gross margin subscription 74.3 % 73.3 % 75.8 % 73.8 % 75.8 % Non-GAAP gross margin subscription 77.3 % 75.2 % 78.1 % 76.2 % 78.1 %

GAAP gross loss professional services

$ (2,731) $ (3,579) $ (3,983) $ (6,310) $ (8,243) Stock-based compensation 144 116 236 260 501 Reduction in workforce 317 — — 317 —

Non-GAAP gross loss professional services $ (2,270) $ (3,463) $ (3,747) $ (5,733) $ (7,742)

GAAP gross margin professional services (226) % (541) % (205) % (337) % (227) % Non-GAAP gross margin professional services (187) % (523) % (193) % (306) % (213) %

GAAP gross profit $ 22,739 $ 24,572 $ 21,747 $ 47,311 $ 43,127

Impact of non-GAAP adjustments 1,496 841 1,019 2,337 2,090 Non-GAAP gross profit $ 24,235 $ 25,413 $ 22,766 $ 49,648 $ 45,217 GAAP gross margin 64.1 % 62.9 % 60.6 % 63.5 % 60.4 % Non-GAAP gross margin 68.3 % 65.1 % 63.4 % 66.6 % 63.3 %

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GAAP to Non-GAAP Reconciliation:

Operating Expense Three Months Ended Six Months Ended

June 30, 2020 March 31, 2020 June 30, 2019 June 30, 2020 June 30, 2019 Operating expense: GAAP sales and marketing $ 7,683 $ 10,472 $ 8,889 $ 18,155 $ 18,104

Stock-based compensation (748) (672) (662) (1,420) (1,289) Amortization of intangibles (528) (528) (272) (1,056) (544) Reduction in workforce (334) — — (334) —

Non-GAAP sales and marketing $ 6,073 $ 9,272 $ 7,955 $ 15,345 $ 16,271

GAAP research and development $ 13,043 $ 13,822 $ 14,487 $ 26,865 $ 30,212

Stock-based compensation (1,314) (1,163) (1,733) (2,477) (3,437) Reduction in workforce (658) — — (658) — Certain legal expenses — 191 — 191 (191) Capitalization of internally developed software — 21 — 21 —

Non-GAAP research and development

$ 11,071 $ 12,871 $ 12,754 $ 23,942 $ 26,584

GAAP general and administrative $ 6,340 $ 6,576 $ 7,010 $ 12,916 $ 14,303

Stock-based compensation (858) (1,066) (2,030) (1,924) (3,192) Amortization of intangibles — (17) (17) (17) (34) Certain legal expenses — — — — (533) Reduction in workforce (497) — — (497) —

Non-GAAP general and administrative $ 4,985 $ 5,493 $ 4,963 $ 10,478 $ 10,544

GAAP goodwill impairment $ — $ 50,300 $ — $ 50,300 $ —

Goodwill impairment — (50,300) — (50,300) — Non-GAAP goodwill impairment $ — $ — $ — $ — $ —

GAAP operating expense $ 27,066 $ 81,170 $ 30,386 $ 108,236 $ 62,619

Impact of non-GAAP adjustments (4,937) (53,534) (4,714) (58,471) (9,220) Non-GAAP operating expense $ 22,129 $ 27,636 $ 25,672 $ 49,765 $ 53,399

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GAAP to Non-GAAP Reconciliation:

Operating loss

Three Months Ended Six Months Ended

June 30, 2020 March 31, 2020 June 30, 2019 June 30, 2020 June 30, 2019 Operating loss: GAAP operating loss $ (4,327) $ (56,598) $ (8,639) $ (60,925) $ (19,492)

Impact of non-GAAP adjustments 6,433 54,375 5,733 60,808 11,310

Non-GAAP operating income (loss) $ 2,106 $ (2,223) $ (2,906) $ (117) $ (8,182)

Net loss and net loss per share: GAAP net loss $ (4,204) $ (56,335) $ (8,381) $ (60,539) $ (18,920)

Total pre-tax impact of non-GAAP adjustments 6,433 54,375 5,733 60,808 11,310

Non-GAAP net income (loss) $ 2,229 $ (1,960) $ (2,648) $ 269 $ (7,610)

GAAP net loss per share, basic and diluted $ (0.03) $ (0.38) $ (0.06) $ (0.41) $ (0.13) Non-GAAP net income (loss) per share, basic and diluted $ 0.01 $ (0.01) $ (0.02) $ — $ (0.05) Shares used in basic and diluted net loss per share computation 150,078 148,872 144,572 149,475 143,790