Castlight Health Investor Presentation August 2020 (NY S E : C S - PowerPoint PPT Presentation

Castlight Health Investor Presentation August 2020 (NY S E : C S LT) 1

This presentation contains forward-looking statements about Castlight Health’s expectations, plans, intentions, and strategies, including, but not limited to, statements regarding Castlight Health’s second quarter performance and 2020 full year projections, impact of COVID-19, the success of our strategy and our expectations for our future business and financial performance. Statements including words such as “anticipate,” “believe,” “estimate,” “will,” “continue,” “expect,” or “future,” and statements in the future tense are forward-looking statements. These forward-looking statements involve risks and uncertainties, as well as assumptions, which, if they do not fully materialize or prove incorrect, could cause our results to differ materially from those expressed or implied by such forward-looking statements. The risks and uncertainties include those described in Castlight Health’s documents filed with or furnished to the Securities and Exchange Safe Harbor Commission, including the risks set forth in our annual report on Form 10-K filed on February 28, 2020, and our quarterly report on Form 10-Q for the three months Statement ended June 30, 2020, when filed. All forward-looking statements in this press release are expressly qualified in their entirety by these cautionary statements and are based on information available to Castlight Health as of the date hereof. Castlight Health assumes no obligation to update these forward-looking statements. We provide guidance in this presentation, but we will not provide any further guidance or updates on our performance during the quarter unless we do so in a public forum. Please refer to today’s press release 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. 2

Non-GA A P Financial Meas ures To 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 financial performance, 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-GAAP operating 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 amortization of 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, facilitate the analysis of the company’s core operating results and comparison of operating results across reporting periods, and can help enhance 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 financial measure, except that we have not reconciled our non-GAAP operating loss and net loss per share guidance for the full year 2020 to comparable GAAP measures because we do not provide guidance for stock-based compensation expense, and capitalization and amortization of internal-use software, which are reconciling items between GAAP and non-GAAP. The factors that may impact our future stock-based compensation expense, and capitalization and amortization of internal-use software are out of our control and/or cannot be reasonably predicted, and therefore we are unable to provide such guidance without unreasonable effort. Factors include our market capitalization and related volatility of our stock price and our inability to project the 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, measures prepared in accordance with GAAP. Further, these non-GAAP measures may differ from the non-GAAP information used by other companies, including peer companies, and therefore comparability may be limited. Castlight Health encourages investors and others to review the company’s financial information in its entirety and not rely on a single financial measure. 3

Investment Highlights A leading provider of health navigation solutions to employers and health plans Operating in a large and growing market driven by consumer adoption of digital healthcare and need for navigation solutions Launching new high-touch offerings to expand market opportunity and better support customers and members (C are Guides) • Employers • New solutions Multiple ways to grow Mu • Health plans • C OVID-19 related New management team bridges outside healthcare expertise with company experience Non- GA A P profit and pos itive cas h flow in 2Q’2020; expect to approach cash flow breakeven during 2H’2020 4

Castlight at a Glance Our health navigation platform connects hundreds of health vendors, benefits resources, and plan designs into one comprehensive health and wellbeing experience. We guide individuals — based on their unique profile — to the best resources 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 decisions to unlock better healthcare outcomes and maximizing return on healthcare investments. Founded 2008 Employees 400+ Total Addressable Market $8B + Fortune 500 Companies 60+ Lives on the Platform ~20M Invested in the Platform $300+ Records in Data Asset 3B + B + Revenue FY2019 $143M 5

Cigna Agreement Details • S igned an agreement t with C igna to serve their Federal government and Taft-Hartley population • Initial population is several hundred thous and Federal Government employees out of C igna’s 6 million total • Starts J anuary 1, 2021 • E xpect t AR R of ~$2 million* * Not included in Q2’2020 AR R as the agreement was signed in Q3’2020 * Please see Castlight 8-K filed August 5 th , 2020 for additional information 6

Senior Management combines company + healthcare experience Y ears at t Name Previous Experience C S L T Maeve O’Meara 10 10 C hief Executive Officer Will Bondurant 7 C hief Financial Officer Matt Mo Ma Moran <1 <1 S VP of Corporate Development J ayes h Patel 9 S VP , Product and User Experience Angel R os a <1 <1 S VP , C ustomer Experience Tamar R udnick 6 S VP , Marketing 7

A decade of innovation High-Touch S ingle experience (C are Guides ) for the complete Ecos ys tem Omni- health journey Platform channel approach, integration with empathic human Wellbeing framework to concierge guides and enable rapid data proactive outreach Behavioral Challenges, sharing and user to users with identified content, mind/ Health experience gaps in car body/wallet, Pers onalization integration of best global, social, Guides employees in breed partners incentives, to Predictive analytics, Trans parency coaching, cost-efficient, machine learning/AI screening based models, omni- effective, accessible Medical, Rx, dental behavioral health channel, real time comparison, spend care recommendations management, provider quality, network strategy, care planning tools 2010 2015 2016 2017 2018 2019 TODA Y 8

Strategic Priorities Update 2020 Priorities 2Q 2020 Updates • S igned agreement with Cigna • S trong mid/late-stage pipeline Health plan growth strategy • Three customers utilizing full Care Guides portfolio B road launch of Cas tlight • 30+ using free COVID-specific Care Guides Care Guides support • Launched innovative return-to to- R evitalize direct-to to-employer work solutions to support our bus ines s customers • Establishing financial sustainability Optimize operating profile • Non-G AAP profit and pos itive cas h flow in Q2’2020 9

Health Benefits are Challenging to Navigate ? ? How can I How can save money I manage on stres s ? EA P healthcare? better? Health ? ? Benefits Nutrition Financial Program Wellbeing ? Where should I ? Maternity Ma How can I go for my improve Management Ma care? my lifes tyle behaviors ? ? What doctor Mental do I Wellbeing choos e? Health Condition Program Concierge Cos t & quality Ma Management ? How do I know Benefit trans parency Program what benefits are available to me? ? Can I afford my 73% of employees don't understand their care? ? How can I health benefits Health get help with S avings my 70% prefer digital over in-person for a Account condition? portion of their healthcare solutions 10