Q4 FY 2019 | 1

Castlight HealthQ4 2019 Financial & Business Update

February 25, 2020

(NYSE:CSLT)

Q4 FY 2019 | 1

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Safe HarborStatement

This presentation contains forward-looking statements regarding our trends, our strategiesand the anticipated performance of our business, which involve risks and uncertainties,including our guidance for the full year of 2020, expected ARR growth, our licenseagreement with Anthem, our executive leadership, timing of platform migrations, cost

savings efforts, impact of non-renewals, direct and channel sales momentum, our ability toadd additional channel partners, future churn risk, future cash position, and the other risksset forth in our filings with the Securities and Exchange Commission, including the risks setforth in our Annual Report on Form 10-K for the year ended December 31, 2019. These

statements were made as of February 25, 2020, and reflect management’s views andexpectations at that time, and are subject to various risks, uncertainties and assumptions. Ifthis call is replayed after February 25, 2020, the information in the call may no longer becurrent or accurate. We disclaim any obligation to update or revise any forward-looking

statements.

We provide guidance in this presentation, but we will not provide any further guidance orupdates on our performance during the quarter unless we do so in a public forum. Pleaserefer 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 causeactual events or results to differ materially from those contained in our forward-lookingstatements.

This presentation also includes certain non-GAAP metrics, such as non-GAAP gross profitand non-GAAP gross margin, non-GAAP operating expenses, non-GAAP operating incomeand non-GAAP operating loss, and non-GAAP net income and loss per diluted share thatwe 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 thispresentation.

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Non-GAAP Financial Measures

To supplement Castlight Health’s financial statements presented in accordance with generally accepted accountingprinciples (GAAP), we also use and provide investors and others with non-GAAP measures of certain components offinancial performance, including non-GAAP gross profit and margin, non-GAAP operating expense, non-GAAPoperating loss, non-GAAP net loss and non-GAAP net loss per share. Non-GAAP gross profit and margin, non-GAAPoperating expense, non-GAAP operating loss, and non-GAAP net loss exclude stock-based compensation, certain legalexpenses, amortization of intangibles, capitalization and amortization of internal-use software, and lease exit andrelated 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 reportingperiods, 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 GAAPfinancial measure, except that we have not reconciled our non-GAAP operating loss and net loss per share guidancefor the full year 2020 to comparable GAAP operating loss and net loss per share guidance because we do not provideguidance for stock-based compensation expense, and capitalization and amortization of internal-use software, whichare reconciling items between GAAP and non-GAAP operating loss. The factors that may impact our future stock-based compensation expense, and capitalization and amortization of internal-use software are out of our controland/or cannot be reasonably predicted, and therefore we are unable to provide such guidance without unreasonableeffort. Factors include our market capitalization and related volatility of our stock price and our inability to project thecost 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-GAAPinformation 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 notrely on a single financial measure.

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Maeve O’MearaCEO

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• $147.0 million as of 12/31/19

• 7% sequential ARR growth, reflecting expansion of the Anthem agreement and renewal activity in Q4 2019

• 75% of total ARR on CastlightComplete or Anthem

• Signed in October, renews and expands the Engage health navigation relationship

• Provides Anthem a non-exclusive enterprise license for components of our underlying platform technology

• ~$170 million total contract value (TCV) for 30 months, effective 1/1/20

Annualized Recurring Revenue (ARR)Impact of

Anthem Enterprise License Agreement

ARR and Related Metrics

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Completed all customer migrations off legacy stack

Q4: Progress Against Key Priorities

Q4 FY 2019 | 7

Completed all customer migrations off legacy stack

Launched first Castlight Care Guides pilot

Q4: Progress Against Key Priorities

Q4 FY 2019 | 8

Completed all customer migrations off legacy stack

Launched first Castlight Care Guides pilot

Hired experienced Commercial leader

Q4: Progress Against Key Priorities

Q4 FY 2019 | 9

Completed all customer migrations off legacy stack

Launched first Castlight Care Guides pilot

Hired experienced Commercial leader

Q4: Progress Against Key Priorities

Unlock growth with health plan strategy

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2020 Priorities

Revitalize direct-to-employer business

Deliver Castlight Care Guides

Jump-start our health plan growth strategy

Optimize operating profile

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Will BondurantCFO

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Increasing Stability in Book of Business

75% 25%

2019

ARR=

$147M

Point SolutionsAt-risk of elevated churn, but constitutes

progressively smaller portion of our book of business

Complete / AnthemRepresents the majority of the book of business;

ARR exceeded the range due to contribution from the Anthem enterprise

license agreement and improvement on renewals

Customers on Castlight Complete and the renewed Anthem agreement reduces risk in overall book of business

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Income Statement Review

Category Metric Commentary

Revenue $36.4 million

• Within full year guidance range

• $0.9mm of non-recurring revenue from end of

customer contracts & performance guarantees

Non-GAAP*

Gross Margin 58%

• Includes impact of one-time factors: write-off

of amortized professional services fees for

terminated customers and investment in UT

Customer Center of Excellence

Operating Expenses $29.2 million• S&M: write-off of amortized commissions

• G&A: includes executive recruiting

Operating

Income/(Loss)($8.1) million

* Please see Appendix for definition of non-GAAP financial measures

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$59.4 million

Cash Metrics

Cash* as of December 31, 2019

$4.0 million

Q4 2019 Cash Flow from Operations

* Cash, cash equivalents and marketable securities

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2020 Guidance

Guidance as of 2/25/20. Please see Appendix for reconciliation of non-GAAP financial measures.

Metric Range Comment

GAAP Revenue $130mm – $135mm• Includes impact of new Anthem ent. agreement

• 2019 terminations effective in 2020

• Fewer direct-to-employer sales with 2020 launches

Non-GAAP Operating

Income/(Loss)($17)mm – ($22)mm

• S&M within long-term range of 20-24%

• Reduction in R&D from elimination of the Jiff platform,

but will continue above long-term range of 20-24%

• Increase in G&A due to costs of security, compliance,

and operational investments

Non-GAAP EPS ($0.12) – ($0.15)

Weighted Avg. Shares

Outstanding150mm – 151mm

Cash Used in Operations ($12)mm – ($17)mm

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Q&A Session

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Appendix

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Gross Profit: Reconciliation of GAAP to Non-GAAP

December 31, 2018 March 31, 2019 June 30, 2019 September 30, 2019 December 31, 2019

Gross profit:

GAAP gross profit subscription 31,589 25,640 25,730 26,383 25,573

Stock-based compensation 222 219 196 180 179

Amortization of internal-use software 120 - - - -

Amortization of intangibles 678 587 587 660 530

Non-GAAP gross profit subscription $32,609 $26,446 $26,513 $27,223 $26,282

GAAP gross margin subscription 80.2 % 75.8 % 75.8 % 75.6 % 73.6 %

Non-GAAP gross margin subscription 82.7 % 78.2 % 78.1 % 78.0 % 75.7 %

GAAP gross loss professional services and other ($4,210) ($4,260) ($3,983) ($5,423) ($5,426)

Stock-based compensation 239 265 236 236 216

Non-GAAP gross loss professional services ($3,971) ($3,995) ($3,747) ($5,187) ($5,210)

GAAP gross margin professional services and other (156.0%) (253.0%) (205.0%) (967.0%) (314.7%)

Non-GAAP gross margin professional services and other (148.0%) (237.0%) (193.0%) (925.0%) (302.2%)

GAAP gross profit $27,379 $21,380 $21,747 $20,960 $20,147

Impact of non-GAAP adjustments 1,259 1,071 1,019 1,076 925

Non-GAAP gross profit $28,638 $22,451 $22,766 $22,036 $21,072

GAAP gross margin 65.0% 60.2% 60.6% 59.1% 55.3%

Non-GAAP gross margin 68.0% 63.3% 63.4% 62.1% 57.8%

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Operating Expense: Reconciliation of GAAP to Non-GAAP

December 31, 2018 March 31, 2019 June 30, 2019 September 30, 2019 December 31, 2019

Operating expenses:

GAAP sales and marketing $10,419 $9,215 $8,889 $9,829 $10,664

Stock-based compensation (615) (627) (662) (678) (175)

Amortization of intangibles (273) (272) (272) (528) (529)

Non-GAAP sales and marketing $9,531 $8,316 $7,955 $8,623 $9,960

GAAP research and development $14,531 $15,725 $14,487 $14,295 $14,487

Stock-based compensation (1,854) (1,704) (1,733) (1,294) (1,369)

Certain legal expenses - (191) - - -

Capitalization of internally developed software - - - - 80

Acquisition related costs (167) - - - -

Non-GAAP research and development $12,510 $13,830 $12,754 $13,001 $13,198

GAAP general and administrative $6,220 $7,293 $7,010 $6,440 $7,238

Stock-based compensation (1,193) (1,162) (2,030) (625) (1,217)

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

Certain legal expenses - (533) - - -

Non-GAAP general and administrative $5,010 $5,581 $4,963 $5,799 $6,005

GAAP operating expense $31,170 $32,233 $30,386 $30,564 $32,389

Impact of non-GAAP adjustments (4,119) (4,506) (4,714) (3,141) (3,226)

Non-GAAP operating expense $27,051 $27,727 $25,672 $27,423 $29,163

Operating loss:

GAAP operating loss ($3,791) ($10,853) ($8,639) ($9,604) ($12,242)

Impact of non-GAAP adjustments 5,378 5,577 5,733 4,217 4,151

Non-GAAP operating loss (income) $1,587 ($5,276) ($2,906) ($5,387) ($8,091)