Castlight Health : Q3 2020 Financial & Business Update

Castlight Health

Q3 2020 Financial & Business Update

November 5, 2020

(NY S E : C S L T)

Q3 2020 | 1

Safe

Harbor

Statement

This presentation contains forward-looking statements within the meaning of the federal securities laws about Castlight Health's expectations, plans, intentions, and strategies which include, but are not limited to, statements regarding Ca stlight Health's third quarter 2020 performance and 2020 full year projections, the impact of C O VID-19, the success of our strategy, and our expectations for our future business and financial performance. Statements including words such a s "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 E xchange Commission, including the risks set forth in our annual report on Form 10-K for the year ended December 31, 2019 as filed with the S E C on February 28, 2020, and our quarterly reports on Form 10- Q, including the quarterly report for the three months ended S eptember 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, except as required by law.

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 R e gulation F D compliant forum. Please refer to today's press release and the risk factors included in the company's filings with the Securities and Exchange C ommission for discussion of important factors that may cause actual events or res ults to differ materially from thos e contained in our forward-looking statements.

Q3 2020 | 2

Non-G A A P F inanc ial 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. However, these non-GAAPfinancial measures should be considered in addition to, not as a substitute for or in isolation from, measures prepared in accordance

with GAAP.

The non-GAAP measures we provide 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.

In the third quarter 2020 earnings press release, 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.

Q3 2020 | 3

Maeve O'Meara, CEO

Q3 2020 | 4