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to approve the issuance of shares of Castlight Class B common stock in connection with the merger of Neptune Acquisition Subsidiary, Inc., a wholly owned subsidiary of Castlight, with and into Jiff, Inc. (“Jiff”), with Jiff surviving as a wholly owned subsidiary of Castlight, as contemplated by the Agreement and Plan of Merger and Reorganization, dated as of January 4, 2017 (which is referred to as the merger agreement), by and among Castlight, Jiff and Neptune Acquisition Subsidiary, Inc. (the “Share Issuance Proposal”);

2.	to approve the adjournment of the Castlight special meeting, if necessary or appropriate, to solicit additional proxies if there are not sufficient votes to approve the issuance of the shares of Castlight Class B common stock in connection with the merger (the “Adjournment Proposal”); and

3.	to transact such other business as may properly come before the special meeting.

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•	the addition or loss of large customers, including through acquisitions or consolidations of such customers;

•	seasonal and other variations in the timing of the sales of its offering, as a significantly higher proportion of its customers enter into new subscription agreements with it or renew previous agreements in the third and fourth quarters of the year compared to the first and second quarters;

•	the timing of recognition of revenue, including possible delays in the recognition of revenue due to lengthy and sometimes unpredictable implementation timelines;

•	failure to meet its contractual commitments under service-level agreements with its customers;

•	the amount and timing of operating expenses related to the maintenance and expansion of its business, operations and infrastructure;

•	its access to pricing and claims data managed by health plans and other third parties, or changes to the fees Castlight pay for that data;

•	the timing and success of introductions of new products, services and pricing by it or its competitors or any other change in the competitive dynamics of its industry, including consolidation among competitors, customers or strategic partners;

•	its ability to attract new customers;

•	customer renewal rates and the timing and terms of customer renewals;

•	network outages or security breaches;

•	the mix of products and services sold or renewed during a period;

•	general economic, industry and market conditions;

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•	the timing of expenses related to the development or acquisition of technologies or businesses and potential future charges for impairment of goodwill from acquired companies; and

•	impact of new accounting pronouncements.

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•	the price, performance and functionality of its offering;

•	its customers’ user counts and benefit design features;

•	the availability, price, performance and functionality of competing or alternative solutions;

•	the potential for customers that are able to access lower-functionality versions of its offering that Castlight provides through health plans or other channel partners to opt to use the lower-functionality versions of its offering;

•	its ability to develop complementary products and services;

•	its continued ability to access the pricing and claims data necessary to enable it to deliver reliable data in its cost estimation and price transparency offering to customers;

•	the stability, performance and security of its hosting infrastructure and hosting services;

•	changes in health care laws, regulations or trends; and

•	the business environment of its customers, in particular, headcount reductions by its customers.

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•	breach of its contractual obligations to customers, which may cause its customers to terminate their relationship with it and may result in potentially significant financial obligations to its customers;

•	investigation by the federal and state regulatory authorities empowered to enforce HIPAA, which include the U.S. Department of Health and Human Services and state attorneys general, and the possible imposition of civil penalties;

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•	private litigation by individuals adversely affected by any violation of HIPAA, HITECH or comparable state laws for which Castlight is responsible; and

•	negative publicity, which may decrease the willingness of current and potential future customers to work with it and negatively affect its sales and operating results.

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•	cease offering or using technologies that incorporate the challenged intellectual property;

•	make substantial payments for legal fees, settlement payments or other costs or damages;

•	obtain a license, which may not be available on reasonable terms, to sell or use the relevant technology; or

•	incur substantial costs and reallocate resources to redesign its technology to avoid infringement.

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•	inability to integrate or benefit from acquired technologies or services in a profitable manner;

•	unanticipated costs or liabilities associated with the acquisition;

•	difficulty integrating the accounting systems, operations and personnel of the acquired business;

•	difficulties and additional expenses associated with supporting legacy products and hosting infrastructure of the acquired business;

•	difficulty converting the customers of the acquired business onto its platform and contract terms, including disparities in the revenue, licensing, support or professional services model of the acquired company;

•	diversion of management’s attention from other business concerns;

•	adverse effects to its existing business relationships with business partners and customers as a result of the acquisition;

•	the potential loss of key employees;

•	use of resources that are needed in other parts of its business; and

•	use of substantial portions of its available cash to consummate the acquisition.

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•	Castlight’s and/or Jiff’s employees may experience uncertainty regarding their future roles in the combined company, which might adversely affect Castlight’s and/or Jiff’s ability to retain, recruit and motivate key employees and executives;

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the attention of Castlight’s and/or Jiff’s management may be directed towards the completion of the merger and other transaction-related considerations and may be diverted from the day-to-day business operations of Castlight and/or Jiff, as applicable, and matters related to the merger may require commitments of time and resources that could otherwise have been devoted to other opportunities that might have been beneficial to Castlight and/or Jiff, as applicable; and

•	customers, partners and other third parties with business relationships with Castlight and/or Jiff may decide not to renew or may decide to seek to terminate, change and/or renegotiate their relationships with Castlight and/or Jiff as a result of the merger, whether pursuant to the terms of their existing agreements with Castlight and/or Jiff or otherwise.

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•	diversion of management focus and resources from operational matters and other strategic opportunities while working to implement the merger;

•	reputational harm due to the adverse perception of any failure to successfully complete the merger; and

•	having to pay certain costs relating to the merger, such as legal, accounting, financial advisory, filing and printing fees.

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•	investors react negatively to the prospects of the combined company’s business and prospects from the merger;

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•	the effect of the merger on the combined company’s business and prospects is not consistent with the expectations of financial or industry analysts; or

•	the combined company does not achieve the perceived benefits of the merger as rapidly or to the extent anticipated by financial or industry analysts.

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•	the inability to successfully combine the businesses of Castlight and Jiff in a manner that permits the combined company to achieve the synergies anticipated to result from the merger, which would result in the anticipated benefits of the merger not being realized partly or wholly in the time frame currently anticipated or at all;

•	lost sales and customers as a result of certain customers of either of the two companies deciding not to do business with the combined company;

•	complexities associated with managing the combined businesses;

•	integrating personnel from the two companies;

•	creation of uniform standards, controls, procedures, policies and information systems;

•	potential unknown liabilities and unforeseen increased expenses, delays or regulatory conditions associated with the merger; and

•	performance shortfalls at one or both of the two companies as a result of the diversion of management’s attention caused by completing the merger and integrating the companies’ operations.

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•	overall performance of the equity markets;

•	Castlight’s operating performance and the performance of other similar companies;

•	changes in the estimates of its operating results that Castlight provides to the public or its failure to meet these projections;

•	failure of securities analysts to maintain coverage of Castlight, changes in financial estimates by securities analysts who follow Castlight or its failure to meet these estimates or the expectations of investors or changes in recommendations by securities analysts that elect to follow Castlight Class B common stock;

•	sales of shares of Castlight Class B common stock by Castlight or its stockholders;

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•	announcements of technological innovations, new products or enhancements to services, acquisitions, strategic alliances or significant agreements by Castlight or by its competitors;

•	disruptions in its services due to computer hardware, software or network problems;

•	announcements of customer additions and customer cancellations or delays in customer purchases;

•	recruitment or departure of key personnel;

•	the economy as a whole, market conditions in its industry and the industries of its customers;

•	litigation involving Castlight, its industry or both, or investigations by regulators into its operations or those of its competitors;

•	developments or disputes concerning its intellectual property or other proprietary rights;

•	new laws or regulations or new interpretations of existing laws or regulations applicable to its business; and

•	the size of Castlight’s market float.

•	adoption of a merger or consolidation agreement involving Castlight;

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•	a sale, lease or exchange of all or substantially all of Castlight’s property and assets;

•	a dissolution or liquidation of Castlight; or

•	every matter, if and when any individual, entity or “group” (as such term is used in Regulation 13D of the Exchange Act) has, or has publicly disclosed (through a press release or a filing with the SEC) an intent to have, beneficial ownership of 30% or more of the number of outstanding shares of Castlight Class A and Class B common stock, combined.

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•	the Castlight Board is classified into three classes of directors with staggered three-year terms and directors are only able to be removed from office for cause, which may delay the replacement of a majority of the Castlight Board or impede an acquirer from rapidly replacing Castlight’s existing directors with its own slate of directors;

•	subject to the rights of the holders of any series of Castlight preferred stock to elect directors under specified circumstances, only the Castlight Board has the right to fill a vacancy created by the expansion of the Castlight Board or the resignation, death or removal of a director, which prevents stockholders from being able to fill vacancies on the Castlight Board;

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Castlight’s stockholders may not act by written consent or call special stockholders’ meetings; as a result, a holder, or holders, controlling a majority of Castlight Class A and Class B common stock are not be able to take certain actions other than at annual stockholders’ meetings or special stockholders’ meetings, which special meetings may only be called by the chairman of the Castlight Board, its chief executive officer, its president, or a majority of the Castlight Board;

•	certain litigation against Castlight can only be brought in Delaware;

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Castlight’s restated certificate of incorporation authorizes undesignated Castlight preferred stock, the terms of which may be established and shares of which may be issued, by the Castlight Board without the approval of the holders of Castlight Class B common stock, which makes it possible for the Castlight Board to issue Castlight preferred stock with voting or other rights or preferences that could impede the success of any attempt to acquire Castlight;

•	advance notice procedures and additional disclosure requirements apply for stockholders to nominate candidates for election as directors or to bring matters before a meeting of stockholders, which may discourage or deter a potential acquirer from conducting a solicitation of proxies to elect the acquirer’s own slate of directors or otherwise attempting to obtain control of Castlight;

•	Castlight’s restated certificate of incorporation prohibits cumulative voting in the election of directors, which limits the ability of minority stockholders to elect director candidates;

•	amendment of the anti-takeover provisions of Castlight’s restated certificate of incorporation require super majority approval by holders of at least two-thirds of Castlight’s outstanding Class A and Class B common stock, combined; and

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in certain circumstances pertaining to change in control, the sale of all or substantially all of Castlight’s assets and liquidation matters, and on all matters if and when any individual, entity or group has, or has publicly disclosed an intent to have, beneficial ownership of 30% or more of the number of outstanding shares of Castlight Class A and Class B common stock, combined, holders of Castlight Class A common stock are entitled to ten votes per share and holders of Castlight Class B common stock are entitled to one vote per share. As of December 31, 2016, holders of Castlight Class A common stock owned 52.1% and the holders of Castlight Class B common stock owned 47.9% of the outstanding shares of Castlight Class A and Class B common stock, combined. However, because of Castlight’s dual class common stock structure these holders of Castlight Class A common stock have 91.6% and holders of Castlight Class B common stock have 8.4% of the total votes with respect to the matters specified above. In all other circumstances, holders of Castlight Class A and Class B common stock are each entitled to one vote per share, and in these other circumstances the holders of Castlight Class A common stock have 52.1% and holders of Castlight Class B common stock have 47.9% of the total votes.

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1.

to approve the issuance of shares of Castlight Class B common stock in connection with the merger of Neptune Acquisition Subsidiary, Inc., a wholly owned subsidiary of Castlight, with and into Jiff, with Jiff surviving as a wholly owned subsidiary of Castlight, as contemplated by the Agreement and Plan of Merger and Reorganization, dated as of January 4, 2017 (which is referred to as the merger agreement), by and among Castlight, Jiff and Neptune Acquisition Subsidiary, Inc. (the “Share Issuance Proposal”);

2.	to approve the adjournment of the Castlight special meeting, if necessary or appropriate, to solicit additional proxies if there are not sufficient votes to approve the issuance of the shares of Castlight Class B common stock in connection with the merger (the “Adjournment Proposal”); and

3.	to transact such other business as may properly come before the special meeting.

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•	vote in person - Castlight will provide a ballot to stockholders who attend the special meeting and wish to vote in person; or

•	vote by mail - if you request or receive a paper proxy card and voting instructions by mail, simply complete, sign and date the enclosed proxy card and return it before the special meeting in the envelope provided.

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•	delivering to Castlight’s Corporate Secretary (by any means, including facsimile) a written notice stating that the proxy is revoked;

•	signing and delivering a proxy bearing a later date; or

•	attending and voting at the special meeting (although attendance at the special meeting will not, by itself, revoke a proxy).

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•	each of Castlight’s and Jiff’s business, operations, financial condition, asset quality, earnings and prospects;

•	the strategic fit of the businesses of the two companies, including their complementary markets, products, research and development, business lines, sales infrastructures and approaches to the wellbeing and engagement space;

•	the opportunity to leverage complementary customer bases and sales channels to more effectively market both company’s products to potential customers, and thereby increase combined company sales at a faster rate than either would expect if each company was operating on a standalone basis;

•	the amounts and timing of the cost savings, related expenses and revenue synergies expected to result from the proposed merger;

•	the expectation that the combined company would create long-term stockholder value by creating additional growth opportunities by leveraging the respective strengths of each business and expanding the combined company’s development pipeline and research and development activities;

•	the potential for expansion in the growing market for health benefit platform solutions;

•	its understanding of the current and prospective environment in which Castlight and Jiff operate, including national, state and local economic conditions, the competitive environment for companies in the health benefit platform solutions generally, and the likely effect of these factors on Castlight both with and without the proposed transaction;

•	its review and discussions with Castlight’s management concerning the due diligence investigation of Jiff, including its review of Jiff’s financial condition, results of operation, market areas, growth potential and intellectual property;

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the opinion of Allen & Company, dated January 4, 2017, to the Special Committee as to the fairness, from a financial point of view and as of the date of the opinion, to Castlight of the aggregate base consideration of 27,000,000 shares of Castlight Class B common stock to be paid by Castlight pursuant to the merger agreement upon the completion of the merger, which opinion was based on and subject to the various assumptions made, procedures followed, matters considered and qualifications and limitations on the review undertaken as set forth in such opinion

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the financial and other terms of the merger agreement, the portion of the total merger consideration based on future events and contingent performance measures, expected tax treatment, the no-shop covenants and prohibitions on Jiff’s ability to seek alternative acquisition proposals, the other deal protection and termination provisions, and restrictions on the conduct of Jiff’s business between the date of the merger agreement and the date of completion of the merger, which it reviewed with its outside legal advisors.

•	Castlight management’s attention and Castlight resources may be diverted from the operation of Castlight’s business and towards the completion of the merger;

•	Castlight may not realize all of the anticipated benefits of the merger, including cost savings, maintenance of existing customer and employee relationships, and minimal disruption in the integration of the Jiff operations and sales infrastructure with Castlight;

•	the challenges and difficulties relating to integrating the operations of Jiff and Castlight;

•	the nature and amount of payments and other benefits to be received by Jiff equity holders in connection with the merger pursuant to the merger agreement;

•	the risk that because the exchange ratio is fixed, the value of the stock to be issued by Castlight in connection with the merger could fluctuate and increase between the original signing of the merger agreement and the completion of the transactions contemplated by the merger agreement;

•	the risk that the combination with Jiff might not be completed in a timely manner or at all and the attendant adverse consequences for Castlight and Jiff’s respective businesses as a result of the pendency of the combination and operational disruption; and

•	the substantial costs that Castlight will incur in connection with the merger and other transactions contemplated by the merger agreement, even if they are not consummated.

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•	Market Development. The Jiff Board considered the anticipated costs, timing and risks associated with developing the market and increasing the number of customers using Jiff’s products, and other factors potentially impacting the revenues and profitability of enterprise health benefits platform products generally.

•	Cost of Additional Capital. The Jiff Board considered the need for substantial additional financing in order to fund Jiff’s operations and achieve profitability, if at all, and the associated dilution to Jiff stockholders that would result from such financing.

•	Competitive Risks. The Jiff Board considered Jiff’s competitive position in the enterprise health benefits platform industry and competitive risks, including potential future competition from larger and better funded companies which might have competitive advantages from their broader commercial scope and economies of scale in pricing.

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Risk of Non-Consummation. The Jiff Board considered the fact that, while Jiff expects that the merger will be completed, there can be no assurance that the conditions to the merger will be satisfied, and that as a result, the merger may not be completed. The Jiff Board considered the potential risks associated with a failure of the merger to be completed, including (i) the extensive time and effort expended by Jiff’s directors, senior management and other employees during the pendency of the merger, (ii) the significant transaction-related costs and opportunity costs incurred by Jiff, and (iii) Jiff’s business could be disrupted and negatively impacted, including loss of business partners and employees.

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Contingent Consideration. The Jiff Board considered the fact that a significant portion of the merger consideration is in the form of the Earnout Payments and hence contingent upon future events and that there were no guarantees that such future events will occur. The Jiff Board also considered the fact that the merger consideration received by Jiff stockholders could be subject to indemnification claims by Castlight and its related parties under the merger agreement.

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Restrictions on Conduct of Business. The Jiff Board considered the limitations on Jiff’s pursuit of business opportunities during the pendency of the merger due to certain covenants contained in the merger agreement requiring Jiff to operate its business in the ordinary course of business consistent with past practice and, subject to specified exceptions, to comply with certain other operating restrictions. Such restrictions could delay or prevent Jiff from pursuing business opportunities that may arise during the pendency of the merger and/or have a material adverse effect on Jiff’s ability to respond to changing market and business conditions, in a timely manner, or at all.

•	Impact of Announcement on Jiff. The Jiff Board considered the impact on Jiff’s business of the public announcement of the merger, including the potentially negative effects that such announcement may have on Jiff’s business relationships and its ability to attract and retain key management and other personnel during the pendency of the merger.

•	Inability to Solicit Other Takeover Proposals. The Jiff Board considered the covenant in the merger agreement prohibiting Jiff from soliciting other potential acquisition proposals, and restricting its ability to entertain other potential acquisition proposals.

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Interests of the Jiff Board. The Jiff Board considered the fact that Jiff’s directors and officers may have financial interests in the transactions contemplated by the merger agreement that may be different from or in addition to those of Jiff’s other stockholders, and the risk that these interests might influence their decision with respect to the transactions contemplated by the merger agreement.

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•	reviewed the financial terms and conditions of the merger as reflected in an execution version, provided to Allen & Company on January 4, 2017, of the merger agreement;

•	reviewed certain publicly available historical business and financial information relating to Castlight and certain historical business and financial information relating to Jiff, including public filings of Castlight and historical market prices for Castlight Class B common stock;

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reviewed certain financial information relating to Castlight and Jiff, including certain internal financial forecasts, estimates and other financial and operating data relating to Castlight prepared by the management of Castlight for the fiscal years ending December 31, 2016 and December 31, 2017, and certain financial forecasts, estimates and other financial and operating data relating to Jiff prepared by the management of Jiff, as adjusted by the management of Castlight, for the fiscal years ending December 31, 2016 through December 31, 2019;

•	held discussions with the managements of Castlight and Jiff relating to the past and current operations and financial condition and prospects of Castlight and Jiff;

•	held discussions with the management of Castlight as to the strategic rationale for, and certain contemplated benefits (including potential cost savings and revenue enhancements) expected by the management of Castlight to result from, the merger;

•	reviewed and analyzed certain publicly available information, including certain stock market data and financial information, relating to selected companies with businesses that Allen & Company deemed generally relevant in evaluating Castlight and Jiff;

•	reviewed certain publicly available financial information relating to selected transactions that Allen & Company deemed generally relevant in evaluating the merger;

•	reviewed the relative contributions of Castlight and Jiff to certain financial metrics of the pro forma combined company based on the internal financial forecasts, estimates and other financial and operating data of Castlight and Jiff referred to above; and

•	conducted such other financial analyses and investigations as Allen & Company deemed necessary or appropriate for purposes of its opinion.

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•	historical trading prices of Castlight Class B common stock during the 52-week period ended January 3, 2017, which indicated low to high intraday prices for Castlight Class B common stock during such period of approximately $2.54 to $5.50 per share; and

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to the extent publicly available, one-year forward stock price targets for Castlight Class B common stock as reflected in selected publicly available Wall Street research analysts’ reports and other publicly available information as of January 3, 2017, which indicated an overall low to high range of stock price targets for Castlight Class B common stock of $4.00 to $7.00 per share (with a mean of $4.91 per share and a median of $4.73 per share).

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In connection with the completion of the merger, Giovanni Colella, Chief Executive Officer of Castlight, will become the Executive Chairman of Castlight and John C. Doyle, President and Chief Operating Officer of Castlight, will become the Chief Executive Officer of Castlight and a member of the Castlight Board. Neither Dr. Colella nor Mr. Doyle will receive any additional compensation in connection with the merger.

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Bryan Roberts, Chairman of the Castlight Board prior to the completion of the merger, is Partner at Venrock, which beneficially owns 16,825,301 shares of Castlight Class A and Class B common stock, or approximately 16% of Castlight’s total issued and outstanding capital stock. Venrock also owns 8,040,910 shares of Jiff Capital Stock, or approximately 18% of the total issued and outstanding Jiff Capital Stock. The Castlight Board appointed a Special Committee (comprised solely of disinterested directors) to which it delegated the

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•	A reduction in his base salary or target bonus;

•	A relocation of his principal office by more than 50 miles;

•	A material reduction in his duties, authority, reporting relationship or responsibilities;

•	A material violation by Castlight of a material term of any employment, severance or change of control agreement with Castlight; or

•	Failure by a successor entity to Castlight to assume his vesting acceleration benefits (but only during the period that is 3 months preceding and 12 months following a change in control of Castlight).

•	willful failure to substantially perform his duties under his employment agreement;

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•	an act or omission which constitutes gross misconduct or gross negligence;

•	violation of federal or state law or regulation applicable to Jiff’s business;

•	material violation of a written agreement, including his confidential information agreement, with Jiff or of a Jiff policy, or any misappropriation of Jiff funds or property;

•	commission or conviction of, or a plead of “guilty” or “no contest” to, a felony under federal or state law; or

•	material unauthorized use or disclosure of Jiff confidential information.

•	a material diminution in the executive’s base compensation, authorities, duties or responsibilities; or

•	a relocation of the executive’s worksite to a location more than 30 miles from its prior location.

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(1)

Represents 24 months of Mr. Newell’s base salary ($367,000 based on his initial base salary with Castlight), the maximum lump-sum cash severance payment that may be payable upon a termination of employment without cause or a resignation for good reason within the qualifying period beginning 3 months prior to, or within 12 months following, a change of control of Castlight, pursuant to Mr. Newell’s Castlight Executive Severance Agreement. Therefore, in order for Mr. Newell to be eligible for this payment, Castlight must have a change in control following the completion of the merger and Mr. Newell must have a qualifying termination within the qualifying period. Pursuant to Mr. Newell’s Castlight Executive Severance Agreement, if Mr. Newell is subject to a termination of employment without cause or if he resigns for certain good reasons outside of such qualifying period, he will only be eligible to receive a lump-sum cash severance payment equal to 12 months of his base salary. Benefits payable under the Castlight Executive Severance

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(2)

Represents 6 months of the executive’s base salary, the lump-sum cash severance payment that may be payable upon a termination of employment without cause or a resignation for good reason, pursuant to the executive’s employment agreement with Jiff. Such payment is contingent on the executive’s execution and non-revocation of a general release of claims in favor of Jiff and certain related parties. The cash severance is double-trigger in nature.

(3)

Represents the aggregate payments to be made in respect of unvested Jiff options (for which the exercise price is less than $4.17) that accelerate upon a qualifying termination of employment, as described in greater detail with respect to Mr. Newell in the section above entitled “Benefits Waiver” and as described in greater detail with respect to the other executive officers in the section above entitled “Equity Acceleration.” Values in this column reflect a fair market value of Castlight Class B common stock of $4.17, the average closing market price of such shares over the five business day period ending January 11, 2017. For purposes of calculating the per share value of each share of Jiff common stock in the transaction, it has been assumed that each share of Jiff common stock will be exchanged for 0.57 shares of Castlight Class B common stock, which assumes that all contingent payments will, in fact, be paid (the “Exchange Ratio”). The product of $4.17 and the Exchange Ratio, or 2.3769, is referred to as the Per Share Value and is the estimated value of a share of Jiff common stock (assuming all contingent payments will be paid).

(4)

Represents the product of (1) the excess of (x) the Per Share Value over (y) the per share exercise price applicable to each option multiplied by (2) the number of unvested shares subject to such option as of December 31, 2016. The estimate assumes that the number of unvested shares subject to such options on the date of the executive’s termination of employment will equal the number of unvested shares subject to such options on December 31, 2016 and these numbers do not forecast any future grants or exercises that may occur between December 31, 2016 and the date of termination of employment.

(5)

Assumes acceleration of all unvested Jiff options upon a qualifying termination of employment occurring immediately following the completion of the merger, or, in the case of Mr. Newell immediately following the completion of a merger of Castlight. The acceleration for Messrs. Hodge, Kemmerer and Leonard is double trigger in nature. Fifty percent of the acceleration for Mr. Newell is single trigger in nature (with respect to a change of control of Castlight) and 50% of the acceleration for Mr. Newell is double-trigger in nature.

(6)

Represents the maximum value of 24 months of health plan continuation coverage premiums under COBRA for Mr. Newell and, if applicable, for his eligible dependents. Mr. Newell is eligible for such benefits on the same terms and conditions as described under Footnote 1 above in the event of a qualifying termination in connection with, or following, a change of control of Castlight. Outside of such qualifying window, Mr. Newell will only be eligible to receive the aggregate value of 12 months of health plan continuation coverage under COBRA for himself and, if applicable, for his eligible dependents. Such amounts have been calculated assuming a monthly premium of $10,410, the maximum premium payable under Castlight’s health plans as in effect as of January 2017. If Mr. Newell were to be eligible to receive such benefits under Jiff’s health plans as in effect as of January 2017, the monthly premium would be $1,714, for a 24 month total of $41,136.

(7)	Represents the aggregate value of 6 months of health plan continuation coverage premiums under COBRA for the executive. Such amounts have been calculated assuming a monthly premium of $2,189 for Mr. Hodge, $2,172 for Mr. Kemmerer and $1,691 for Mr. Leonard, the applicable premium under Jiff’s health plans as in effect as of January 2017.

(8)

As noted above, pursuant to the employment agreements, in the event that any payments to the executive officers would be subject to the excise tax imposed by Section 4999 of the Code (as a result of such payments being classified as parachute payments under Section 280G of the Code), then such executive officer will receive such payment as would result in the greater of (i) the total transaction-based benefits payable to the executive minus the 20% excise tax imposed by Section 4999 of the Code (i.e., paid by the relevant executive officer) or (ii) the total transaction-based benefits minus the amount necessary to avoid the 20% excise tax imposed by Section 4999 of the Code. The total amounts do

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•	an individual citizen or resident of the United States;

•	a corporation (or any other entity treated as a corporation for U.S. federal income tax purposes) created or organized in or under the laws of the United States, any state thereof or the District of Columbia;

•	an estate the income of which is subject to U.S. federal income taxation regardless of its source; or

•	a trust (i) that is subject to the primary supervision of a court within the United States and all the substantial decisions of which are controlled by one or more U.S. persons or (ii) that has a valid election in effect under applicable U.S. Treasury regulations to be treated as a U.S. person.

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•	will not recognize any gain or loss upon the exchange of shares of Jiff Capital Stock for shares of Castlight Class B common stock in the merger;

•	will have a tax basis in Castlight Class B common stock received in the merger (including fractional shares for which cash is received) equal to the tax basis of Jiff Capital Stock surrendered in exchange therefore; and

•	will have a holding period for shares of Castlight Class B common stock received in the merger (including fractional shares for which cash is received) that includes its holding period for its shares of Jiff Capital Stock surrendered in exchange therefore.

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•	the shares of Castlight Class B common stock that such holder has the right to receive pursuant to the provisions of the merger agreement, net of any amounts deposited with the escrow agent and Stockholder’s Agent (which will be in uncertificated book-entry form); and

•	any cash in lieu of fractional shares of Castlight Class B common stock to which such holder is entitled under the terms of the merger agreement.

•	Each share of Jiff Series A preferred stock held by a Converting Holder immediately prior to the Effective Time shall be canceled and automatically converted into the right to receive a number of shares of Castlight Class B common stock equal to the Jiff Series A preferred stock liquidation preference of $35.545 divided by $4.455 or approximately 7.98 shares of Castlight Class B common stock.

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Each share of Jiff Series B preferred stock and Jiff Series C preferred stock held by a Converting Holder immediately prior to the Effective Time shall be canceled and automatically converted into the right to receive, a number of shares of Castlight Class B common stock equal to (a)(i)(1) the Stock Consideration less (2) the aggregate amount of Castlight Class B common stock issued to the holders of Jiff Series A preferred stock in satisfaction of their

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•	Each share of Jiff common stock held by a Converting Holder immediately prior to the Effective Time shall be canceled and automatically converted into the right to receive the Per Share Common Consideration.

•	Each share of Jiff Starter Stock held by a Converting Holder immediately prior to the Effective Time shall be canceled and automatically converted into the right to the Per Share Common Consideration.

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•	any failure of any representation or warranty made by Jiff in the merger agreement, the Jiff Disclosure Letter, or any exhibit or schedule to the merger agreement to be true and correct as of the date of (i) the merger agreement or (ii) as of the completion of the merger, as applicable;

•	any failure of any certification, representation or warranty made by Jiff in any certificate delivered to Castlight pursuant to the merger agreement (other than the merger proceeds allocation spreadsheet and closing financial certificate regarding Jiff transaction expenses) to be true and correct as of the date such certificate is delivered to Castlight;

•	any breach of, or default in connection with, any of the covenants, agreements or obligations made by Jiff in the merger agreement or in any other agreements contemplated by the transaction documents or the merger;

•	any inaccuracies in the merger proceeds allocation spreadsheet or closing financial certificate regarding Jiff transaction expenses;

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any issuances made with respect to dissenting shares, and any interest, costs, expenses and fees incurred by any Indemnified Person in connection with the exercise of any appraisal rights or dissenters’ rights, to the extent that such amounts, in the aggregate, exceed the value of the consideration that otherwise would have been issuable (based on the Castlight Stock Price) pursuant to the merger agreement upon the exchange of such Dissenting Shares;

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any claims by any then-current holder of any equity interests of Jiff (including any predecessors), arising out of, resulting from or in connection with (I) the allocation of the consideration under the merger agreement or any portion thereof that differs from that specified on the merger proceeds spreadsheet, or (II) for breach of fiduciary duty by the directors and officers of Jiff in connection with the merger agreement and/or the other transactions;

•	any of the matters set forth on the Jiff disclosure letter that constitutes an exception to Jiff's representation regarding the absence of litigation;

•	any taxes for any pre-closing periods to the extent not reflected as an accrual in the applicable Jiff balance sheet, as adjusted for taxes arising in the ordinary course of business consistent with past practice through the completion of the merger; and

•	any intentional fraud, intentional misrepresentation or willful misconduct by or on behalf of Jiff in connection with the merger agreement.

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•	amend or otherwise change Jiff’s certificate of incorporation or bylaws or equivalent organizational documents;

•	merge or consolidate itself with any other Person or adopt a plan of complete or partial liquidation, dissolution, consolidation, restructuring, recapitalization or other reorganization;

•	declare, set aside, make or pay any dividend or other distribution;

•	except in the ordinary course of business, enter into, amend, waive, modify or consent to the termination of any material contract or rights thereunder, or enter into any other contract other than in the ordinary course of business consistent with past practice;

•	issue, deliver, grant or sell or authorize or propose the issuance, delivery, grant or sale of, or purchase or propose the purchase of, any Jiff Voting Debt or any Equity Interests, or enter into or authorize or propose to enter into any Contracts of any character obligating it to issue any Equity Interests, other than Permitted Issuances, as defined in the merger agreement;

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(i) hire, or offer to hire, any additional officers or other employees, or any consultants or independent contractors, (ii) terminate the employment, change the title, office or position, or materially reduce the responsibilities of any employee of Jiff, (iii) enter into, amend or extend the term of any employment or consulting agreement held by, any officer, employee, consultant or independent contractor, (iv) enter into any Contract with a labor union or collective bargaining agreement (unless required by Applicable Law) or (v) add any new members to the Jiff Board;

•	make any loans or advances (other than routine expense advances to employees of Jiff consistent with past practice) to, or any investments in or capital contributions to, any Person, or forgive or discharge in whole or in part any outstanding loans or advances, or prepay any indebtedness for borrowed money;

•	transfer or license from any Person any rights to any Intellectual Property;

•	take any action regarding a patent, patent application or other Jiff Registered Intellectual Property, other than filing continuations for existing patent applications or completing or renewing registrations of existing patents, domain names, trademarks or service marks in the ordinary course of business consistent with past practice;

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•	sell, lease, license or otherwise dispose or permit to lapse of any of its material tangible or intangible assets or enter into any Contract with respect to the foregoing, other than sales and nonexclusive licenses of Jiff Products in the ordinary course of business consistent with past practice;

•	incur any indebtedness for borrowed money or guarantee any such indebtedness;

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pay, discharge or satisfy (i) any Liability to any Person who is an officer, director or stockholder of Jiff (other than compensation due for services as an officer or director) or (ii) any material claim or Liability arising other than in the ordinary course of business consistent with past practice, other than the payment, discharge or satisfaction of Liabilities reflected or reserved against in the Financial Statements and Transaction Expenses, or accelerate payment of any accounts payable;

•	make any capital expenditures, capital additions or capital improvements in excess of $50,000 individually or $100,000 in the aggregate;

•	materially change the amount of any insurance coverage;

•	cancel, release or waive any material claims or rights held by Jiff outside of the ordinary course of business consistent with past practice;

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(i) adopt or amend any employee or compensation benefit plan, including any stock issuance or stock option plan, or amend any compensation, benefit, entitlement, grant or award provided or made under any such plan, except in each case as required under ERISA, Applicable Law or as necessary to maintain the qualified status of such plan under the Code, (ii) materially amend any deferred compensation plan within the meaning of Section 409A of the Code and the regulations thereunder, except to the extent necessary to meet the requirements of such Section or Notice, (iii) pay any special bonus or special remuneration to any employee or non-employee director or consultant or (iv) increase the salaries, wage rates or fees of its employees or consultants other than in the ordinary course of business consistent with past practice;

•	grant or pay, or enter into any Contract providing for the granting of any severance, retention or termination pay, or the acceleration of vesting or other benefits, to any Person;

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(i) commence a lawsuit other than (A) for the routine collection of bills, (B) in such cases where Jiff in good faith determines that failure to commence suit would result in the material impairment of a valuable aspect of its business (provided that Jiff consults with Castlight prior to the filing of such a suit) or (C) for a breach of the merger agreement or (ii) settle or agree to settle any pending or threatened lawsuit or other dispute;

•	acquire any corporation, partnership, limited liability company, other business organization or division thereof or any material amount of assets, or enter into any joint venture, strategic alliance, exclusive dealing, non-competition or similar contract or arrangement;

•	make, revoke or modify any material tax election, settle or compromise any tax liability, file any return other than on a basis consistent with past practice, enter into any agreement with a governmental body with respect to taxes or otherwise enter into a contract with respect to taxes;

•	change accounting methods or practices or revalue any of its assets;

•	enter into any agreement for the purchase, sale or lease of any real property;

•	place or allow the creation of any Encumbrance (other than a Permitted Encumbrance) on any of its material properties;

•	materially change the manner in which it provides warranties, discounts or credits to customers;

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•	enter into any contracts that would be deemed an Interested Party Transaction;

•	take any action that would result in Jiff having one or more subsidiaries; and

•	take or agree in writing or otherwise to take, any of the action that would reasonably be expected to prevent Jiff from performing or cause Jiff not to perform one or more covenants, agreements or obligations required by the merger agreement to be performed by Jiff.

•	solicit, initiate, seek, entertain, knowingly encourage, facilitate, support or induce the making, submission or announcement of any inquiry, expression of interest, proposal or offer that constitutes, or could reasonably be expected to lead to, an Acquisition Proposal (as defined below);

•	enter into, participate in, maintain or continue any communications (except solely to provide written notice as to the existence of these provisions) or negotiations regarding, or deliver or make available to any Person any non-

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•	agree to, accept, approve, endorse or recommend (or publicly propose or announce any intention or desire to agree to, accept, approve, endorse or recommend) any Acquisition Proposal;

•	enter into any letter of intent or any other Contract contemplating or otherwise relating to, or that would reasonably be expected to lead to, any Acquisition Proposal;

•	submit any Acquisition Proposal to the vote of any Jiff stockholders; or

•	enter into any other transaction or series of transactions not in the ordinary course of business consistent with past practice, the consummation of which would impede, interfere with, prevent or delay, or would reasonably be expected to impede, interfere with, prevent or delay, the completion of the merger or the other transactions.

•	any Acquisition Proposal;

•	any inquiry, expression of interest, proposal or offer that constitutes, or would reasonably be expected to lead to, an Acquisition Proposal;

•	other notice that any Person is considering making an Acquisition Proposal; or

•	any request for non-public information relating to Jiff or for access to any of the properties, books or records of Jiff by any Person or Persons other than Castlight and its Representatives that would reasonably be expected to lead to, an Acquisition Proposal.

•	the Jiff Stockholder approval and the Castlight Stockholder approval shall have been duly and validly obtained;

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no Order issued by any court of competent jurisdiction or other legal or regulatory restraint or prohibition preventing the completion of the merger shall be in effect, and no action shall have been taken by any Governmental Entity seeking any of the foregoing, and no Applicable Law or Order shall have been enacted, entered, enforced or deemed applicable to the merger that makes the completion of the merger illegal; and

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all filings with and approvals of any Governmental Entity required to be made or obtained in connection with the transactions shall have been made or obtained and shall be in full force and effect and the applicable waiting period under the HSR Act and other applicable Antitrust Laws shall have expired or early termination of such waiting period shall have been granted by the applicable Governmental Entity.

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the truth and correctness of all representations and warranties of Castlight in the merger agreement on the date of the merger agreement and on the completion of the merger with the same force and effect as if made on the date on which the transaction is to be completed or, if such representations and warranties address matters as of a particular date, then as of that particular date, except where the failure of these representations and warranties to be true and correct, individually or in the aggregate, would not reasonably be expected to have a material adverse effect. Further, the Castlight Special Representations shall be true and correct in all material respects, on and as of the date of the merger agreement and at the completion of the merger as though such representations and warranties were made on and as of such dates (except for representations and warranties that address matters only as to a specified date or dates, which representations and warranties shall be true and correct with respect to such specified date or dates).

•	Jiff shall have received each of the agreements, instruments, certificates and other documents set forth in Section 1.2(a) of the merger agreement; and

•	there shall not have occurred a Material Adverse Effect (as defined below) with respect to Castlight since the Agreement Date that is continuing.

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the truth and correctness of all representations and warranties of Jiff in the merger agreement on the date of the merger agreement and on the completion of the merger with the same force and effect as if made on the date on which the transaction is to be completed or, if such representations and warranties address matters as of a particular date, then as of that particular date, except where the failure of these representations and warranties to be true and correct, individually or in the aggregate, would not reasonably be expected to have a material adverse effect. Further, the Jiff Special Representations shall be true and correct in all material respects, on and as of the date of the merger agreement and at the completion of the merger as though such representations and warranties were made on and as of such dates (except for representations and warranties that address matters only as to a specified date or dates, which representations and warranties shall be true and correct with respect to such specified date or dates);

•	Castlight shall have received each of the agreements, instruments, certificates and other documents set forth in Section 1.2(b) of the merger agreement;

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no Order issued by any court of competent jurisdiction or other legal or regulatory restraint or prohibition limiting or restricting Castlight’s ownership, conduct or operation of the Jiff Business following the completion of the merger, including any Antitrust Restraint, shall be in effect, and no Legal Proceeding seeking any of the foregoing, or any other injunction, restraint or material damages in connection with the merger or the other transactions or prohibiting or limiting the consummation of the transactions, shall be threatened in writing or shall have been commenced and remain pending, in each case by a Governmental Entity of competent jurisdiction;

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no Governmental Entity of competent jurisdiction shall have commenced or threatened in writing to commence any Legal Proceeding challenging or seeking the recovery of a material amount of damages in connection with the merger or the other transactions or seeking to prohibit or limit the exercise by Castlight of any material right pertaining to ownership of Equity Interests of the Surviving Entity.

•	there shall not have occurred a Material Adverse Effect (as defined below) with respect to Jiff since the Agreement Date that is continuing;

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the merger agreement shall have been duly and validly adopted and the merger shall have been duly and validly approved under the DGCL, Jiff’s certificate of incorporation and bylaws, each as in effect at the time of such adoption and approval, by holders of outstanding Jiff Capital Stock representing at least 90% of all shares of Jiff Capital Stock outstanding as of immediately prior to the completion of the merger (voting together as a single class and on an as converted basis); and

•	Jiff shall have delivered to Castlight the notification and evidence required by the terms of Section 280G(b)(5)(B) of the Code.

•	by mutual written consent duly authorized by the Castlight Board and the Jiff Board;

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by either Castlight or Jiff, by written notice to the other, if the completion of the merger shall not have occurred on or before September 30, 2017 or such other date that Castlight and Jiff may agree upon in writing (the “Termination Date”); provided that the right to terminate the merger agreement under this clause shall not be available to any party whose breach of any covenant, agreement or obligation hereunder will have been the principal cause of, or will have directly resulted in, the failure of the completion of the merger to occur on or before the Termination Date;

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•	by either Castlight or Jiff, by written notice to the other, if any Order of a Governmental Entity of competent authority preventing the completion of the merger shall have become final and non-appealable;

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by Castlight, by written notice to Jiff, if (i) there shall have been an inaccuracy in any representation or warranty made by, or a breach of any covenant, agreement or obligation of, Jiff herein and such inaccuracy or breach shall not have been cured within 20 Business Days after receipt by Jiff of written notice of such inaccuracy or breach and, if not cured within such period and at or prior to the completion of the merger, such inaccuracy or breach would result in the failure of any of the conditions set forth in Section 7.1 or Section 7.2 of the merger agreement to be satisfied (provided that no such cure period shall be available or applicable to any such breach that by its nature cannot be cured), (ii) there shall have been a Material Adverse Effect with respect to Jiff which shall not have been cured within 20 Business Days after receipt by Jiff of written notice of such Material Adverse Effect, (iii) Jiff shall have materially breached Section 6.1 or breached Section 6.2 of the merger agreement, or (iv) the applicable Governmental Entity shall have commenced litigation seeking the imposition of an Antitrust Restraint as a condition to the expiration or termination of any applicable waiting period under the HSR Act or other applicable Antitrust Law; or

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by Jiff, by written notice to Castlight, if (i) there shall have been an inaccuracy in any representation or warranty made by, or a breach of any covenant, agreement or obligation of, Castlight herein and such inaccuracy or breach shall not have been cured within 20 Business Days after receipt by Castlight of written notice of such inaccuracy or breach and, if not cured within such period and at or prior to the completion of the merger, such breach would result in the failure of any of the conditions set forth in Section 7.1 or Section 7.2 of the merger agreement to be satisfied (provided that no such cure period shall be available or applicable to any such inaccuracy or breach that by its nature cannot be cured) or (ii) there shall have been a Material Adverse Effect with respect to Castlight which shall not have been cured within 20 Business Days after receipt by Castlight of written notice of such Material Adverse Effect or (iii) Castlight shall have materially breached Section 4.1 or Section 4.2 of the merger agreement.

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(1)	Includes the aggregate number of shares of Jiff Series B preferred stock, Jiff Series C preferred stock, Jiff starter stock and Jiff common stock.

(2)	This represents the portion of the approximately 27,000,000 shares, in the aggregate, potentially issuable at closing to holders of Jiff Series A preferred stock, Series B preferred stock and Series C preferred stock, Jiff starter stock and Jiff common stock, and excludes options to be issued upon the assumption of vested Jiff options.

(3)

The fair value of contingent consideration to be settled in Castlight Class B common shares related to the acquisition is estimated based on the Monte Carlo Simulation Model for the revenue and booking earnouts. The fair value of the contingent consideration is calculated with numerous projected outcomes, the results of which are averaged and then discounted to estimate the present value. Some of the more significant assumptions inherent in the development of Monte Carlo Simulation from the perspective of a market participant, include asset-level volatility, stock price volatility, correlation between stock price and revenue, risk-free rate, weighted average cost of capital (“WACC”), and stock price. However, for the purposes of these unaudited pro forma condensed combined financial statements, using currently available information, such as volatility of Castlight’s revenue and bookings, volatility of Castlight Class B common stock, weighted average cost of capital for Jiff and certain other high-level assumptions, were used by Castlight management.

(4)

The estimated consideration expected to be transferred reflected in these unaudited pro forma condensed combined financial statements does not purport to represent what the actual consideration transferred will be when the merger is completed. In accordance with ASC Topic 805, the fair value of equity securities issued as part of the consideration transferred will be measured on the completion date of the merger at the then-current market price. This requirement will likely result in a per share equity component different from the $3.25 closing price of Castlight Class B common stock on January 27, 2017 that is assumed in these unaudited pro forma condensed combined financial statements and that difference may be material. Castlight believes that an increase or decrease by as much as 10% in the Castlight Class B common stock price on the completion date of the merger from the common stock price assumed in these unaudited pro forma condensed combined financial statements is reasonably possible based upon the recent history of Castlight Class B common stock price. A change in the estimated fair value of Castlight Class B common stock price of 10% would increase or decrease the consideration paid as follows, with a corresponding increase or decrease in the goodwill and other balances recorded in connection with the merger.

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•	adoption of a merger or consolidation agreement involving Castlight;

•	a sale, lease or exchange of all or substantially all of Castlight’s property and assets;

•	a dissolution or liquidation of Castlight; or

•	every matter, if and when any individual, entity or “group” (as such term is used in Regulation 13D of the Exchange Act) has, or has publicly disclosed (through a press release or a filing with the SEC) an intent to have, beneficial ownership of 30% or more of the number of outstanding shares of Castlight Class A and Class B common stock, combined.

•	If Castlight were to seek to amend its certificate of incorporation to increase or decrease the par value of a class of stock, then that class would be required to vote separately to approve the proposed amendment; and

•	If Castlight were to seek to amend its restated certificate of incorporation in a manner that alters or changes the powers, preferences or rights of a class of stock in a manner that affected its holders adversely, then that class would be required to vote separately to approve the proposed amendment.

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Castlight Health Benefits Platform. The functionality of the core Castlight technology is available to all of Castlight’s customers. Castlight’s core technology includes both an employee and a benefits professional experience. The employee-facing web and mobile experiences simplify health care decision making for employees and their families by providing highly relevant, personalized information for medical services that enable informed choices before, during and after receiving health care. The intuitive, natural language search experience includes personalized out-of-pocket cost estimates, clinical quality, patient satisfaction and provider demographic information. Employer programs are integrated into the platform and promoted to employees in relevant situations to drive increased utilization of valuable benefits and services like tele-health, second opinion programs and wellness offerings. Additional features include the ability to manage a tailored care team, personalized tips, evidence-based clinical guidelines, educational content, benefit guides and real-time spend and deductible information. The benefits professional experience empowers human resource leaders with real-time insights into employee engagement with the platform, benefits and programs to identify opportunities to drive better employee engagement and improved outcomes.

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Castlight Pharmacy. Castlight Pharmacy delivers information to guide employees and their families on how to manage their prescription drug spending. Castlight’s pharmacy product enables them to easily search for cost estimates for specific medications at convenient retail locations as well as mail order alternatives and presents multiple ways to save including using generic equivalents and therapeutic area alternatives. Additionally, Castlight Pharmacy is capable of driving improved drug compliance through prescription refill reminders and interfaces with other third-party applications to change and fulfill prescriptions.

•	Castlight Rewards. Castlight Rewards is an incentive system to motivate employees to make better health care decisions. Employers can use Castlight Rewards to encourage employees to learn about their health care, engage with Castlight and a variety of other desired behaviors.

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Castlight Action. Castlight Action is a fully automated solution for benefits professionals to leverage data and predictive analytics to connect employees to the right benefits and programs throughout the year, in a HIPAA-compliant manner. It surfaces insights to the benefits leader, segments and targets the relevant population using personalized, multi-channel campaigns with specific behavior change goals, and delivers real-time aggregate reporting on the impact of those campaigns to the benefits leader. Castlight Action helps enable benefits leaders to unlock the full value of their benefits strategy by bringing the power of data to enable better employee decision-making.

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Castlight Elevate. Castlight Elevate helps employees working through behavioral health conditions or triggers such as depression, anxiety, substance use disorder, insomnia, and stress. Castlight Elevate breaks down the barriers to behavioral health treatment by enabling employees to research behavioral health services, make educated treatment choices, and begin care, all through a personalized experience.

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Castlight Dental. Castlight Dental provides a comprehensive solution for employees to understand and manage their oral health and dental spend. Castlight’s dental product enables employees to search for specific dental procedures, understand the coverage and overall cost of the care, and make optimal choices. Further, Castlight Dental educates employees about common oral health conditions, driving health, productivity, and increased benefit satisfaction for employees.

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Communication and Engagement Services. Castlight offers communications services to drive employee engagement with its offering that span educational presentations, email campaigns, print collateral and employer-specific media. Communications initiatives are typically run during open enrollment, time of product launch and periodically post launch, and are designed to drive employee engagement and change management. The fees for these services are included as part of Castlight’s contracts.

•	Implementation Services. Castlight provides implementation services to its customers to help ensure successful deployment of its offering, including executing required data feeds, loading customer data, configuring products, integrating with third-party and other applications and comprehensive testing. The fees for these services are included as part of Castlight’s contracts.

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Customer Support. Castlight offers end user support to help ensure effective employee use of its platform. Castlight provides telephonic, live chat and email support for employees and their families in the areas of account maintenance, technical issue resolution, and navigation of online services. In addition, Castlight assists employees with finding care, understanding their benefits, and interpreting past claims, bills, and total spend. Castlight also enables employees who may have limited computer access to obtain their personalized health care information using its customer support personnel. The fees for these services are included as part of subscriptions to Castlight’s products.

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•	Scalability. Castlight has developed a robust and scalable data architecture infrastructure, which allows for automated loading and normalization of numerous data sources, including billions of claim transactions in its data warehouse.

•	Standardization. Castlight’s technology assimilates structured and unstructured data from disparate sources, and employs unique algorithms to convert these data into user-friendly information for its users. Additionally, Castlight operates using Services Oriented Architecture principles, with a platform of services that serve to deliver the application in a scalable and standardized way.

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Security. Castlight maintains a formal and comprehensive security program designed to ensure the security and integrity of customer data, protect against security threats or data breaches and prevent unauthorized access to its data or the data of its customers. Castlight strictly regulates and limits all access to on-demand servers and networks at its production and remote backup facilities. All users are authenticated, authorized and validated before they

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•	ability to curate complex data from multiple sources and present it through an easy to navigate user interface;

•	capability for customization through configuration, integration, security, scalability and reliability of products;

•	ease of use and rates of user engagement;

•	complimentary technology platform and high touch services;

•	breadth and depth of application functionality;

•	competitive and understandable pricing;

•	size of customer base and level of user engagement;

•	depth of access to third-party data sources;

•	ability to integrate with legacy enterprise infrastructures and third-party applications;

•	ability to innovate and respond rapidly to customer needs and regulatory changes;

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•	domain expertise in benefits and health care consumerism;

•	accessibility on any browser or mobile device;

•	clearly defined implementation timeline; and

•	customer branding and styling.

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•	limit how Castlight will use and disclose the protected health information;

•	implement reasonable administrative, physical and technical safeguards to protect such information from misuse;

•	enter into similar agreements with its agents and subcontractors that have access to the information;

•	report security incidents, breaches and other inappropriate uses or disclosures of the information; and

•	assist the customer in question with certain duties under the privacy standards.

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(1)	Operating leases for facilities space represents Castlight’s principal commitments, which consists of obligations under leases for office space.

(2)	Data center costs represent costs associated with service agreements for Castlight’s data centers in Colorado and Arizona.

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•	there is persuasive evidence of an arrangement;

•	the service has been provided to the customer;

•	collection of the fees is reasonably assured; and

•	the amount of fees to be paid by the customer is fixed or determinable.

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•	Jiff believes that its designs create an easier to navigate, more visually appealing user experience overall, both on desktop and on mobile.

•	Jiff’s products are more engaging and useful for people who are busy and distracted by numerous forms of media and entertainment competing for their attention. Jiff’s mobile design uses bite-size chunks of content and game mechanics, such as social newsfeeds and feedback loops to keep consumers checking in daily.

•	Jiff’s products, because they are designed with a mobile-first philosophy, are more accessible at the moment users need support, wherever they are. Increasingly, the smartphone is the primary means by which people access the internet.

•	Jiff Launch Pad: Jiff’s entry-level product is a turn-key employee wellbeing platform that can be quickly and easily implemented to offer employees a fun and engaging health program. Launch Pad comes with Activity, Sleep,

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Jiff Total Wellbeing: Total Wellbeing is Jiff’s all-in-one employee wellbeing program, giving employees access to a comprehensive suite of tools spanning physical, mental, and financial health. The solution allows employers to plug in best-in-class direct to consumer and B2B health apps, devices, and services, across 16 categories of heath ranging from activity to biometrics to resilience and financial wellbeing. With Total Wellbeing, employers can easily run high-impact incentives programs that let employees earn points toward rewards such as premium reductions, streaming music subscriptions, sweepstakes for vacations, and more. The platform is highly configurable and is designed from the ground up to meet the unique needs of each employer.

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Jiff Enterprise Navigator: Enterprise Navigator is Jiff’s comprehensive employee health and wellbeing platform that responds to the preferences of each individual. It comes to life for employees in a beautiful, mobile interface, and learns over time as health and benefit needs evolve. Enterprise Navigator is a definitive engagement platform - the first place employees go to get information on all of their company’s benefits and an easy way to find the programs that they need. For employers, it centralizes all of the company’s benefits into a single hub, easing vendor management and giving them real-time feedback on what is working and what is not. Enterprise Navigator is Jiff’s most comprehensive solution, offering its full range of features, programs and configurability, including integrations with all ecosystem partners and custom integrations with non-partners.

•	access to a wide range of third-party data sources and deep expertise in integrating with third-party vendors and legacy enterprise infrastructures;

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•	ability to curate complex data from multiple sources and present it through an easy to navigate user interface;

•	flexibility and customization through configuration, integration, customer branding and styling;

•	security, scalability, reliability, and accessibility of products on any browser or mobile device;

•	breadth and depth of application functionality;

•	competitive and understandable pricing;

•	ability to innovate and respond rapidly to customer needs and regulatory changes;

•	domain expertise in benefits and healthcare consumerism;

•	clearly defined implementation timelines; and

•	size of customer base and rates of user engagement;

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•	each person, or group of affiliated persons, known by it to be the beneficial owner of more than 5% of Castlight Class A and Class B common stock;

•	each of Castlight’s directors or director nominees;

•	each of Castlight’s named executive officers; and

•	all of Castlight’s directors and executive officers as a group.

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*	Represents beneficial ownership of less than 1% of Castlight’s outstanding shares of common stock.

(1)

Percentage of total voting power represents voting power with respect to all shares of Castlight’s Class A and Class B common stock, as a single class. Generally, the holders of Castlight’s Class B common stock and Class A common stock are entitled to one vote per share. However, holders of Castlight’s Class A common stock are entitled to ten votes per share in certain circumstances, if submitted to a vote of stockholders, including: (i) adoption of a merger or consolidation agreement involving the Company; (ii) a sale, lease or exchange of all or substantially all of the Company’s property and assets; (iii) a dissolution or liquidation of the Company; and (iv) on every matter, if and when any individual, entity or “group” (as such term is used in Regulation 13D of the Exchange Act) has, or has publicly disclosed (through a press release or a filing with the SEC) an intent to have, beneficial ownership of 30% or more of the number of outstanding shares of Class A common stock and Class B common stock, combined. Holders of shares of Class A common stock and Class B common stock vote together as a single class on all matters (including those set forth in this joint proxy statement/prospectus/information statement) submitted to a vote of stockholders, unless otherwise required by Castlight’s certificate of incorporation or bylaws. The Class B common stock is convertible at any time by the holder into shares of Class A common stock on a share-for-share basis.

(2)

Shares owned are as of December 30, 2016, according to a Schedule 13G/A filed with the SEC on February 13, 2017. FMR LLC has sole power to vote or direct the vote of 1,222,700 shares and the sole power to dispose of all 12,753,365 shares. Members of the family of Abigail P. Johnson, Director, the Vice Chairman, the Chief Executive Officer and the President of FMR LLC, are the predominant owners, directly or through trusts, of Series B voting common shares of FMR LLC, representing 49% of the voting power of FMR LLC. The Johnson family group and all other FMR LLC

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(3)

Shares owned are as of December 31, 2016, according to a Schedule 13G/A filed with the SEC on February 14, 2017. These securities are owned by Neil Gagnon and by various individuals and institutional investors (the “Accounts”) of which Mr. Gagnon as managing member and principal owner of Gagnon Securities LLC is the investment manager. Mr. Gagnon has sole voting and dispositive power over 277,433 shares of the Class B common stock and Mr. Gagnon has shared voting power over 2,521,191 shares of Class B common stock and shared dispositive power over 2,554,088 shares of Class B common stock. Mr. Gagnon and GS may be deemed to share voting power with respect to 1,499,276 shares of Class B common stock held in the Accounts and dispositive power with respect to 1,521,428 shares of Class B common stock held in the Accounts.. Gagnon Securities LLC and Mr. Gagnon expressly disclaim beneficial ownership of all securities held in the Accounts. Mr. Gagnon is also the Chief Executive Officer of Gagnon Advisors, LLC (“Gagnon Advisors”). Mr. Gagnon and Gagnon Advisors in its role as investment manager to Gagnon Investment Associates, LLC may be deemed to share voting and dispositive power with respect to the 894,725 shares of Class B common stock held by Gagnon Investment Associates, LLC. Mr. Gagnon expressly disclaims beneficial ownership of all securities held by Gagnon Investment Associates, LLC. The address for Mr. Gagnon is 1370 Avenue of the Americas, 24th Floor, New York, NY 10019.

(4)

Shares owned are as of December 31, 2016, according to a Schedule 13G/A filed with the SEC on February 14, 2017. These securities consist of (a) 7,733,386 shares of Class A common stock, (b) 1,144,324 shares of Class B common Stock, (c) options exercisable for 25,000 shares of Class B common stock within 60 days of December 31, 2016 and (d) 7,812 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016. Maverick Capital, Ltd. (“Maverick Capital”) is an investment adviser registered under Section 203 of the Investment Advisers Act of 1940 and, as such, may be deemed to have beneficial ownership of such shares through the investment discretion it exercises over its clients’ accounts. Maverick Capital Management, LLC is the General Partner of Maverick Capital. Lee S. Ainslie III is the manager of Maverick Capital Management, LLC. Andrew H. Warford serves as the Chairman of the Stock Committee of Maverick Capital. The address for Maverick Capital is 300 Crescent Court, 18th Floor, Dallas, TX 75201. Mr. Singer is a managing director of Maverick Capital.

(5)

Shares owned are as of December 31, 2016, according to a Schedule 13G/A filed with the SEC on February 14, 2017. These securities consist of (a) 11,917,744 shares of Class A common stock held directly by Oak Investment Partners XII, Limited Partnership and (b) options exercisable for 48,437 shares of Class B common stock within 60 days of December 31, 2016, 25,000 of which may be deemed to be held by Ann Lamont on behalf of Oak Investment Partners XII, Limited Partnership. Ann Lamont, Bandel L. Carano, Edward F. Glassmeyer, Fredric W. Harman, and Grace A. Ames collectively serve as managing members of Oak Associates XII, LLC, the General Partner of Oak Investment Partners XII, L.P. Such Managing Members have shared voting and investment control over all of the shares held by Oak Investment Partners XII, L.P. The address of Oak Investment Partners XII, L.P. is 901 Main Avenue, Suite 600, Norwalk, CT 06851.

(6)

Shares owned are as of December 31, 2016, according to a Schedule 13G/A filed with the SEC on February 9, 2017. The Vanguard Fiduciary Trust Company is a wholly-owned subsidiary of The Vanguard Group. These securities consist of (a) 78,781 shares of Class B common stock held by the Vanguard Fiduciary Trust Company and (b) 2,405,620 shares of Class B common stock, held directly by the Vanguard Group. The address of the entities affiliated with The Vanguard Group is 100 Vanguard Blvd., Malvern, PA 19355.

(7)

Shares owned are as of October 30, 2015, according to a Schedule 13D filed with the SEC on November 20, 2015. These securities consist of (a) 14,047,522 shares of Class A common stock, held directly by Venrock Associates V, L.P., (b) 330,053 shares of Class A common stock, held directly by Venrock Entrepreneurs Fund V, L.P. and (c) 1,190,996 shares of Class A common stock, held directly by Venrock Partners V, L.P., (d) 1,133,948 shares of Class B common

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(8)	Shares owned are as of May 17, 2016, according to a Schedule 13D filed with the SEC on May 27, 2016. SAP Technologies, Inc. is a wholly owned indirect subsidiary of SAP SE. SAP SE is a Societas Europaes organized in the Federal Republic of Germany.

(9)

Consists of (a) 28,430 shares of Class B common stock held directly by Mr. Colella; (b) 4,350,753 shares of Class A common stock held directly by the Giovanni and Vanessa Colella Revocable Living Trust dated 11/26/05 (the “Living Trust”), of which Dr. Colella is a co-trustee, (c) 5,426 shares of Class B common stock held directly by the Living Trust, (d) 600,000 shares of Class A common stock held directly by The Giovanni Matteo Colella 2016 Grantor Retained Annuity Trust – I, of which Dr. Colella is trustee, (e) 250,000 shares of Class A common stock held directly by The Giovanni Matteo Colella 2016 Grantor Retained Annuity Trust – II, of which Dr. Colella is trustee, (f) 600,000 shares of Class A common stock held directly by The Vanessa Stevens Colella 2016 Grantor Retained Annuity Trust I, of which Vanessa Colella is trustee, (g) 250,000 shares of Class A common stock held directly by The Vanessa Stevens Colella 2016 Grantor Retained Annuity Trust II, of which Vanessa Colella is trustee, (h) options exercisable for 46,500 shares of Class A common stock within 60 days of December 31, 2016 (i) options exercisable for 337,500 shares of Class B common stock within 60 days of December 31, 2016, and (j) 85,437 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016. Dr. Colella is trustee and sole beneficiary of The Giovanni Matteo Colella 2016 Grantor Retained Annuity Trust - I and The Giovanni Matteo Colella 2016 Grantor Retained Annuity Trust - II. Dr. Colella retains voting and investment power over shares held by The Giovanni Matteo Colella 2016 Grantor Retained Annuity Trust - I and The Giovanni Matteo Colella 2016 Grantor Retained Annuity Trust - II.

(10)

Consists of (a) 30,475 shares of Class B common stock held directly by Mr. Doyle, (b) options exercisable for 870,000 shares of Class A common stock within 60 days of December 31, 2016, (c) options exercisable for 150,000 shares of Class B common stock within 60 days of December 31, 2016 and (d) 39,500 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016.

(11)	Consists of (a) options exercisable for 79,996 shares of Class B common stock within 60 days of December 31, 2016 and (b) 51,250 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016.

(12)	Consists of 7,812 shares of Class B common stock.

(13)

Consists of (a) 28,571 shares of Class A common stock, (b) 28,125 shares of Class B common stock, (c) options exercisable for 260,973 shares of Class A common stock within 60 days of December 31, 2016, (d) options exercisable for 25,000 shares of Class B common stock within 60 days of December 31, 2016 and (e) 7,812 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016.

(14)	See footnote 6. Ms. Lamont is a managing member of Oak Associates XII, LLC, the General Partner of Oak Investment Partners XII, L.P. Ms. Lamont and the other managing members have shared voting and investment control over all of the shares held by Oak Investment Partners XII, L.P., and as such, she may be deemed to have voting and investment power with respect to these shares.

(15)	Consists of (a) 28,571 shares of Class A common stock held directly by Mr. Park, (b) 28,125 shares of Class B common stock, (c) options exercisable for 47,220 shares of Class B common stock within 60 days of December 31, 2016 and (d) 7,812 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016.

(16)	See Footnote 8. Dr. Roberts is a member of the general partners of Venrock Associates V, L.P., Venrock Entrepreneurs Fund V, L.P. and Venrock Partners V, LP, and as such, he may be deemed to have voting and investment power with

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(17)	Consists of (a) 28,125 shares of Class B common stock, (b) options exercisable for 25,000 shares of Class B common stock within 60 days of December 31, 2016 and (c) 7,812 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016.

(18)	Consists of (a) 4,196 shares of Class B common stock and (b) 4,197 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016.

(19)

Consists of (a) 33,565,639 shares of Class A common stock, (b) 1,554,416 shares of Class B common stock, (c) options exercisable for 1,220,661 shares of Class A common stock within 60 days of December 31, 2016, (d) options exercisable for 740,152 shares of Class B common stock within 60 days of December 31, 2016 and (e) 276,272 shares of Class B common stock issuable upon the settlement of restricted stock units within 60 days of December 31, 2016.

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•	each person, or group of affiliated persons, known by it to the beneficial owner of more than 5% of Jiff Capital Stock;

•	each of Jiff’s directors or director nominees;

•	each of Jiff’s named executed officers; and

•	all of Jiff’s directors and executive officers as a group.

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(1)	Percentage of total voting power represents voting power with respect to all shares of Jiff Capital Stock (voting together as a single class on an as converted basis). The holders of Jiff Capital Stock are entitled to one vote per share. The shares

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(2)

Shares owned are as of December 31, 2016. These securities consist of (i) 733,659 warrants for Jiff common stock exercisable within 60 days of December 31, 2016 held directly by Aberdare Ventures IV, L.P., (ii) 117,106 shares of Jiff Series A preferred stock held directly by Aberdare Ventures IV, L.P., (iii) 2,337 shares of Jiff Series A preferred stock held directly by Aberdare Partners IV, L.P., (iv) 4,625,616 shares of Jiff Series B preferred stock held directly by Aberdare Ventures IV, L.P., (v) 92,475 shares of Jiff Series B preferred stock held directly by Aberdare Partners IV, L.P., (vi) 1,258,964 shares of Jiff Series C preferred stock held directly by Aberdare Ventures IV, L.P., (vii) 25,129 shares of Jiff Series C preferred stock held directly by Aberdare Partners IV, L.P. and (viii) 1,155,682 shares of Jiff Series C preferred stock held directly by Transformational Healthcare Opportunity (JIFF), LLC. Mr. Hite is a member of the general partner of Aberdare Ventures IV, L.P., Aberdare Partners IV, L.P. and Transformational Healthcare Opportunity (JIFF), LLC, and as such, he may be deemed to have voting and investment power with respect to these shares. The address of the entities affiliated with Aberdare is 235 Montgomery Street, Suite 1230, San Francisco, CA 94104.

(3)

Shares owned are as of December 31, 2016. These securities are owned directly by EVP Technology Fund III GmbH & Co. KG and consist of (i) 259,203 warrants for Jiff common stock exercisable within 60 days of December 31, 2016, (ii) 42,200 shares of Jiff Series A preferred stock, (iii) 3,652,246 shares of Jiff Series B preferred stock and (iv) 1,540,910 shares of Jiff Series C preferred stock. The address of EVP Technology Fund III GmbH & Co. KG. is Boxbergring 107, 69126 Heidelberg, Germany.

(4)	Shares owned are as of December 31, 2016. These securities are owned directly by Johnson and Johnson Innovation – JJDC, Inc. and consist of 3,595,495 shares of Jiff Series C preferred stock. The address of Johnson and Johnson Innovation – JJDC, Inc. is 410 George Street, New Brunswick, NJ 08901.

(5)	Shares owned are as of December 31, 2016. These securities are owned directly by Robert Derek Newell and consist of (i) options exercisable for 2,107,094 shares of Jiff common stock within 60 days of December 31, 2016, (ii) 488,739 warrants for Jiff common stock exercisable within 60 days of December 31, 2016 and (iii) 10,052 shares of Jiff Series B preferred stock.

(6)

Shares owned are as of December 31, 2016. These securities are owned directly by Ooga Labs LLC and consist of (i) 2,258,126 warrants for Jiff common stock exercisable within 60 days of December 31, 2016, (ii) 159,901 shares of Jiff common stock, (iii) 2,741,525 shares of Jiff starter stock and (iv) 25,130 shares of Jiff Series B preferred stock. Messrs. Currier and Chudnovsky are members of Ooga Labs LLC, and as such, they may be deemed to have voting and investment power with respect to these shares. The address of Ooga Labs LLC is 558 Hawthorne Street, Palo Alto, CA 94301.

(7)	Shares owned are as of December 31, 2016. These securities are owned directly by Rosemark I, L.P. consist of 4,848,757 shares of Jiff Series C preferred stock. The address of Rosemark I, L.P. is 90 Nassau, Princeton, NJ 08542.

(8)	Shares owned are as of December 31, 2016. These securities are owned directly by Towers Watson Delaware, Inc. and consist of (i) 261,600 warrants for Jiff common stock exercisable within 60 days of December 31, 2016 and (ii) 3,595,459 shares of Jiff Series C preferred stock. The address of Towers Watson Delaware, Inc. is 1450 Brickell Avenue, Miami, FL 33131.

(9)

Shares owned are as of December 31, 2016. These securities consist of (i) 6,026,800 shares of Jiff Series B preferred stock held directly by Venrock Associates VI, L.P., (ii) 473,200 shares of Jiff Series B preferred stock held directly by Venrock Partners VI, L.P., (iii) 1,428,732 shares of Jiff Series C preferred stock held directly by Venrock Associates VI, L.P. and (iv) 112,178 shares of Jiff Series C preferred stock held directly by Venrock Partners VI, L.P. Mr. Kocher is a member of the general partner of Venrock Associates VI, L.P. and Venrock Partners VI, L.P., and as such, he may be deemed to have voting and investment power with respect to these shares. The address of the entities affiliated with Venrock is 3340 Hillview Avenue, Palo Alto, CA 94304.

(10)	Consists of options exercisable for 220,895 shares of Jiff common stock within 60 days of December 31, 2016.

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(11)	Consists of options exercisable for 177,604 shares of Jiff common stock within 60 days of December 31, 2016.

(12)	Consists of options exercisable for 200,520 shares of Jiff common stock within 60 days of December 31, 2016.

(13)	Includes (i) options exercisable for 2,754,305 shares of Jiff common stock within 60 days of December 31, 2016 and (ii) 3,739,727 warrants for Jiff common stock exercisable within 60 days of December 31, 2016.

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•	selecting a firm to serve as the independent registered public accounting firm to audit Castlight’s financial statements;

•	ensuring the independence of the independent registered public accounting firm;

•	discussing the scope and results of the audit with the independent registered public accounting firm, and reviewing, with management and that firm, Castlight’s interim and year-end operating results;

•	establishing procedures for employees to submit, anonymously, concerns about questionable accounting or audit matters;

•	considering the adequacy of Castlight’s internal controls and internal audit function;

•	reviewing material related party transactions or those that require disclosure;

•	approving or, as permitted, pre-approving all audit and non-audit services to be performed by the independent registered public accounting firm; and

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•	monitoring security management and compliance with other legal and regulatory requirements.

•	reviewing and approving, or recommending that the Castlight Board approve, the compensation of Castlight’s executive officers;

•	reviewing and approving, or recommending that the Castlight Board approve, the compensation of Castlight’s directors;

•	administering Castlight’s stock and equity incentive plans;

•	reviewing and approving, or making recommendations to the Castlight Board with respect to, incentive compensation and equity plans; and

•	reviewing Castlight’s overall compensation philosophy.

•	identifying and recommending candidates for membership on the Castlight Board;

•	reviewing and recommending Castlight’s corporate governance guidelines and policies;

•	reviewing proposed waivers of the code of conduct for directors and executive officers;

•	overseeing the process of evaluating the performance of the Castlight Board; and

•	assisting the Castlight Board on corporate governance matters.

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(1)

Amounts listed under the “Stock Awards” and “Option Awards” columns represent the aggregate fair value amount computed as of the grant date of each award during 2016 in accordance with Financial Accounting Standards Board (“FASB”) Accounting Standards Codification (“ASC”) Topic 718. The fair value of these awards is based on the closing price of Castlight Class B common stock on the grant date. As required by SEC rules, the amounts shown exclude the impact of estimated forfeitures related to service-based vesting conditions. Castlight’s directors will only realize compensation from these stock awards to the extent that they satisfy service-based vesting conditions in the terms of the RSUs. For information regarding the number of awards held by each non-employee director as of December 31, 2016, see the table below.

(2)	Appointed on June 22, 2016.

(3)	Resigned on March 28, 2016.

(4)	Appointed on August 28, 2016.

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•	$30,000 annual cash retainer;

•	$30,000 for the independent chair of the Castlight Board;

•	$16,000 for the chair of the Castlight Audit Committee and $8,000 for each of its other members;

•	$10,000 for the chair of the Castlight Compensation and Talent Committee and $5,000 for each of its other members; and

•	$6,000 for the chair of the Castlight Nominating and Corporate Governance Committee and $3,000 for each of its other members.

•	$15,000 for the Lead Independent Director (if any).

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•	Giovanni M. Colella, the Chief Executive Officer, Co-Founder and Director (the “CEO”);

•	John C. Doyle, the President and Chief Operating Officer; and

•	John McCracken, the Chief Revenue Officer.

(1)

The amount reported in the Non-Equity Incentive Plan Compensation column represents the cash incentive bonus paid to Dr. Colella and Mr. Doyle under Castlight’s incentive bonus plan for executive officers. For 2015, each of Dr. Colella and Mr. Doyle was eligible to receive incentive cash bonuses, based on Castlight’s achievement of certain strategic objectives, including objectives relating to customer acquisition and retention, new product introduction and operational metrics as determined by the Castlight Compensation and Talent Committee. Dr. Colella’s target bonus was 100% of base salary and Mr. Doyle’s target bonus was 50% of base salary. Based on Castlight’s and the individuals’ achievement toward the above objectives, the Castlight Compensation and Talent Committee approved a bonus of 32% of target for Dr. Colella and a bonus of 40% of target for Mr. Doyle. For 2016, each of Dr. Colella and Mr. Doyle was eligible to receive incentive cash bonuses, based on Castlight’s achievement of certain strategic objectives, including objectives relating to customer acquisition and retention, new product introduction and operational metrics as determined by the Castlight Compensation and Talent Committee. The cash incentive bonuses for 2016 are not calculable as of the date of this filing, and are expected to be determined in the first quarter of 2017.

(2)

The amounts reported in the Stock Awards column represent the grant date fair value and re-pricing date incremental fair value of the stock options and time-based and performance-based restricted stock units, as applicable, granted to the named executive officers during 2015 and 2016 as computed in accordance with ASC 718. The assumptions used in calculating the grant date fair value of the stock options reported in the Option Awards column are set forth in Note 11 in the section entitled “Consolidated Financial Statements of Castlight—Consolidated Financial Statements—Notes to Consolidated Financial Statements.” Note that the amounts reported in this column reflect the accounting cost for these stock options, and do not correspond to the actual economic value that may be received by the named executive officers from the options.

(3)

Represents the grant date fair market value of 305,000 time-based restricted stock unit awards and the target value of 315,000 performance-based restricted stock unit awards. See the 2016 Outstanding Equity at Fiscal-Year end Table below for details on the vesting terms of these awards. The maximum achievable value of the performance-based restricted stock unit awards, assuming 150% attainment of the performance-based award target, was $1,412,775. It was

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(4)

Represents the grant date fair market value of 147,000 time-based restricted stock unit awards and 147,000 performance-based restricted stock unit awards. See the 2016 Outstanding Equity Awards at Fiscal Year-End Table below for details on the vesting terms of these awards. The maximum achievable value of the performance-based restricted stock unit awards, assuming 150% attainment of the performance-based award target, was $3,325,875. It was subsequently determined that the performance threshold for the attainment of the performance-based award was not met; therefore the performance-based award was canceled and no value for that award was achieved.

(5)

Represents the target value of 425,000 time-based restricted stock unit awards and 125,000 performance-based restricted stock unit awards. See the 2016 Outstanding Equity at Fiscal-Year end Table below for details on the vesting terms of these awards. The maximum achievable value of the performance-based restricted stock unit awards, assuming 150% attainment of the performance-based award target, was $560,625. It was subsequently determined that the performance threshold for the attainment of the performance-based award was not met; therefore the performance-based award was canceled and no value for that award was achieved.

(6)

Represents the target value of 132,000 time-based restricted stock unit awards and 44,000 performance-based restricted stock unit awards. See the 2016 Outstanding Equity Awards at Fiscal Year-End Table below for details on the vesting terms of these awards. The maximum achievable value of the performance-based award, assuming 150% attainment, was $1,791,900. It was subsequently determined that the performance threshold for the attainment of the performance-based award was not met; therefore the performance-based award was canceled and no value for that award was achieved.

(7)	Mr. McCracken was not a named executive officer in 2015.

(8)

Represents the target value of 400,000 time-based restricted stock unit awards, 125,000 performance-based restricted stock unit awards. See the 2016 Outstanding Equity at Fiscal-Year end Table below for details on the vesting terms of these awards. The maximum achievable value of the performance-based award, assuming 150% attainment, was $560,625. It was subsequently determined that the performance threshold for the attainment of the performance-based award was not met; therefore the performance-based award was canceled and no value for that award was achieved.

(9)	The amount reported in the All Other Compensation column represents contributions to the officer’s 401(k) plan account of $3,170, plus reimbursement of $108 club membership, $1,491 for continuing education, $1,889 for dues for memberships, $1,746 for meals, $1,200 for license fee, and $457 for subscriptions.

(10)	The amounts reported in the All Other Compensation column represents reimbursement of $216 for membership for a social organization, $2,908 for subscription fees and $400 for identity theft and fraud protection.

(11)	The amount reported in the All Other Compensation column represents contributions to the officer’s 401(k) plan account.

(12)	The amounts reported in the All Other Compensation column represents reimbursement of $844 for professional membership and subscription fees.

(13)	Represents commissions earned by Mr. McCracken under his commission plan as Chief Revenue Officer.

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(1)	Market value of the shares is based on the closing price of Castlight Class B common stock on December 30, 2016 of $4.95.

(2)	This stock option vests with respect to 2.0833% of the underlying shares of Castlight Class B common stock in forty-eight substantially equal installments upon the completion of each consecutive month of service following the vesting commencement date.

(3)	These restricted stock units vest (a) with respect to 25% of the underlying shares of Castlight Class B common stock on the one-year anniversary of the holder’s vesting commencement date, (b) with respect to the remaining underlying shares, in 12 substantially equal installments upon the completion of each additional quarter year of service thereafter.

(4)

These performance stock units could have vested between 100% and 300% of the stated threshold amount based on the achievement of certain performance factors as certified by the Castlight Compensation Committee (such number of shares, if any, referred to as the “Certified RSU Shares”). Once achievement of these performance factors was evaluated and the number of Certified RSU Shares, if any, was determined, the Certified RSU Shares underlying the award would then vest in eight substantially equal installments, beginning on February 16, 2017 and upon the completion

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(5)

This stock option vests (a) with respect to 20% of the underlying shares of Castlight Class A common stock on the one-year anniversary of the holder’s vesting commencement date and (b) with respect to the remaining underlying shares, in 36 substantially equal installments each consisting of 2.2222% of the underlying shares of Castlight Class A common stock upon the holder’s completion of each additional consecutive month of service thereafter.

(6)	This stock option vests (a) with respect to 20% of the underlying shares of Castlight Class A common stock on the one-year anniversary of the holder’s vesting commencement date and (b) with respect to the remaining underlying shares, in 16 substantially equal installments upon the completion of each additional quarter year of service thereafter.

(7)	This stock option vests in 60 substantially equal installments each consisting of 1.6667% of the underlying shares of Castlight Class A common stock upon the holder’s completion of each additional consecutive month of service thereafter.

(1)	Includes 10,541,666 shares subject to restricted stock units.

(2)	The weighted average exercise price relates solely to outstanding stock option shares since shares subject to restricted stock units have no exercise price.

(3)

Includes 6,000,000 shares of common stock that remain available for purchase under the 2014 Employee Stock Purchase Plan and 8,575,400 shares of common stock that remain available for purchase under Castlight’s 2014 Equity Incentive Plan. Additionally, Castlight’s 2014 Equity Incentive Plan provides for annual increases in the number of shares available for issuance under it on January 1 of each of the calendar years during the term of the Plan by 5% of the number of shares of common stock issued and outstanding on each December 31 of the immediately prior year or such lesser amount determined by the Castlight Board. Similarly, Castlight’s 2014 Employee Stock Purchase Plan provides for automatic annual increases in the number of shares available for issuance under it on January 1 of each of the calendar years during the term of the Plan by 1% of the number of shares of common stock issued and outstanding on each December 31 of the immediately prior year or such lesser amount determined by the Board of Directors.

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(1)	Represents the grant date fair value of Jiff option awards granted to the officer, computed in accordance with FASB ASC Topic 718. See Note 2 to the audited financial statements included in this joint proxy statement/prospectus/information statement for a discussion of the assumptions made by Jiff in determining the grant date fair value of Jiff equity awards.

(2)

Represents an option granted on July 21, 2016 for Mr. Newell to purchase 1,090,977 shares of Jiff common stock at an exercise price of $0.67 per share. The option is subject to vesting over a four-year period, with 25% of the option shares vesting on the one-year anniversary of the grant date and 1/48th of the option shares vesting monthly thereafter, subject to Mr. Newell’s continued service with Jiff on each vesting date.

(3)	Represents a bonus to be paid in March 2017, in recognition of Mr. Newell’s 2016 performance.

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•	willful failure to substantially perform his duties under his employment agreement;

•	act or omission which constitutes gross misconduct or gross negligence;

•	violation of federal or state law or regulation applicable to Jiff’s business;

•	material violation of a written agreement, including his confidential information agreement, with Jiff or of a Jiff policy, or any misappropriation of Jiff funds or property;

•	commission or conviction of, or a plea of “guilty” or “no contest” to, a felony under federal or state law; or

•	material unauthorized use or disclosure of Jiff confidential information.

•	a material diminution in his base compensation, authorities, duties or responsibilities; or

•	a relocation of his worksite to a location more than 30 miles from its prior location.

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(1)	Represents 6 months of Mr. Newell’s current base salary of $300,000.

(2)	Represents the aggregate cost of Mr. Newell’s monthly COBRA premiums (consisting of medical and dental coverage) under Jiff’s plans for a period of 6 months following the date of termination, based on the rates in effect on December 31, 2016.

(1)	Option vests over four years of continuous service following October 8, 2014, with 33% of the option shares vesting on such date and the remainder vesting in 32 substantially equal monthly installments thereafter.

(2)

In addition, (i) if Jiff is subject to a change in control before Mr. Newell’s continuous service with Jiff terminates, 50% of the then-unvested option shares will vest, and (ii) if Mr. Newell’s service with Jiff is terminated by Jiff without cause or if Mr. Newell resigns for good reason within 12 months after such change in control, 100% of the then-unvested option shares will vest. However, in connection with the merger, Mr. Newell has executed a waiver of the aforementioned vesting acceleration benefits, as further described in “The Merger - Interests of Certain Jiff Persons in the Merger- Benefits Waiver.”

(3)	Option vests over four years of continuous service following the grant date of July 21, 2016, with 25% of the option shares vesting on the one-year anniversary of the grant date and 1/48th of the option shares vesting monthly thereafter.

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•	not later than December 30, 2016, if the proposal is submitted for inclusion in Castlight’s proxy materials for that meeting pursuant to Rule 14a-8 under the Securities Exchange Act of 1934; or

•	on or after March 9, 2017, and on or before April 8, 2017, if the proposal is submitted pursuant to Castlight’s bylaws, in which case the notice of the proposal must meet certain requirements set forth in Castlight’s bylaws and Castlight will not be required to include the proposal in Castlight’s proxy materials.

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(1)	Includes stock-based compensation expense as follows:

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•	there is persuasive evidence of an arrangement;

•	the service has been provided to the customer;

•	collection of the fees is reasonably assured; and

•	the amount of fees to be paid by the customer is fixed or determinable.

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A.

The boards of directors of each of Castlight, Merger Sub and Jiff have determined that it would be advisable, fair and in the best interests of each corporation or limited liability company and their respective stockholders or members, as applicable, that Castlight acquire Jiff through the statutory merger of Merger Sub with and into Jiff, pursuant to which Jiff would become a wholly owned subsidiary of Castlight (the “Merger”) upon the terms and conditions set forth in this Agreement and in accordance with the applicable provisions of Applicable Law, and in furtherance thereof, have approved this Agreement, the Merger and the other transactions contemplated by this Agreement (the “Transactions”).

B.	Pursuant to the Merger, among other things, all of the issued and outstanding shares of Jiff Capital Stock shall be converted into the right to receive shares of Castlight Class B Common Stock on the terms and subject to the conditions set forth herein.

C.

The board of directors of Jiff (the “Jiff Board”) has carefully considered the terms of this Agreement and has unanimously (1) declared this Agreement and the Transactions, including the Merger, upon the terms and subject to the conditions set forth herein, advisable, fair to and in the best interests of Jiff and Jiff Stockholders, (2) approved this Agreement in accordance with Applicable Law and (3) adopted a resolution directing that the adoption of this Agreement and approval of the principal terms of the Merger be submitted to Jiff Stockholders for consideration and recommending that all of Jiff Stockholders adopt this Agreement and approve the principal terms of the Merger.

D.

The board of directors of Merger Sub has (1) declared this Agreement and the Transactions, including the Merger, upon the terms and subject to the conditions set forth herein, advisable, fair to and in the best interests of Merger Sub and the stockholder of Merger Sub and (2) adopted resolutions recommending that Castlight, as the sole stockholder of Merger Sub, adopt this Agreement and approve the Merger.

E.

The special committee (the “Castlight Special Committee”) of the board of directors of Castlight (the “Castlight Board”) has carefully considered the terms of this Agreement and has (1) declared this Agreement and the Transactions, including the Merger, upon the terms and subject to the conditions set forth herein, advisable, fair to and in the best interests of Castlight and the Castlight Stockholders, (2) approved this Agreement in accordance with Applicable Law and (3) adopted a resolution directing that the approval of the issuance of shares of Castlight Class B Common Stock in connection with the Merger be submitted to Castlight Stockholders for consideration and recommending that all Castlight Stockholders approve the issuance of shares of Castlight Class B Common Stock in connection with the Merger.

F.	Castlight, Merger Sub and Jiff intend that the Merger qualify as a tax-free “reorganization” within the meaning of Section 368(a) of the Code, and this Agreement is intended to constitute a “plan of reorganization” within the meaning of Treasury Regulation Sections 1.368-2(g) and 1.368-3.

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G.

Concurrently with the execution of this Agreement, and as a condition and inducement to Castlight’s and Merger Sub’s willingness to enter into this Agreement, Derek Newell (“Mr. Newell”) (the “Named Employee”) has executed (1) an employment offer letter, together with a confidential information and invention assignment agreement (together, an “Offer Letter”) and (2) a non-competition agreement (a “Non-Competition Agreement”), each to become effective upon the Closing.

H.

Concurrently with the execution of this Agreement, and as a condition and inducement to Castlight’s and Merger Sub’s willingness to enter into this Agreement, the Named Employee is executing a benefits waiver in favor of Jiff and Castlight in substantially the form attached hereto as Exhibit B (a “Benefits Waiver”) and, between the Agreement Date and the Closing, the Key Employees that are Continuing Employees will execute a Benefits Waiver, in each case, to become effective upon the Closing.

I.

Concurrently with the execution of this Agreement, and as a condition and inducement to Jiff’s willingness to enter into this Agreement, (i) certain stockholders of Castlight identified on Schedule A-1 are executing a support agreement in favor of the Transaction, including the Merger, in substantially the form attached hereto as Exhibit F (the “Support Agreement”) and (ii) certain stockholders of Castlight identified on Schedule A-2 are executing lock-up agreements in substantially the form attached hereto as Exhibit E (a “Lock-Up Agreement”).

J.

Concurrently with the execution and delivery of this Agreement, and as a condition and inducement to Castlight’s willingness to enter into this Agreement, the Jiff Stockholders identified on Schedule B (the “Consenting Stockholders”), are executing (i) a stockholder agreement in substantially the form attached hereto as Exhibit C (the “Stockholder Agreement”), (ii) a joinder agreement in substantially the form attached hereto as Exhibit H (a “Joinder Agreement”) and (iii) Lock-Up Agreements.

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(a)	The Earnout Payments will be determined as follows:

(i)	Net New Bookings Earnout. If Final Net New Bookings for FY2017 equals or exceeds $25,000,000 (the “Net New Bookings Milestone”), the Jiff Stockholders and Jiff Optionholders will be entitled to the Bookings Earnout Payment.

(ii)	New Revenue Earnout. If Final New Revenue for FY2017 equals or exceeds $25,000,000 (the “New Revenue Milestone”), the Jiff Stockholders and Jiff Optionholders will be entitled to the Revenue Earnout Payment.

(b)

Castlight shall prepare and deliver to the Stockholders’ Agent no later than 75 calendar days after the end of FY 2017 a calculation of the Net New Bookings and New Revenue generated during such fiscal year (the “Earnout Statement”). Subject to the Stockholders’ Agent entering into a customary confidentiality agreement with Castlight, Castlight shall provide the Stockholders’ Agent with all relevant information (in electronic format, if available) that the Stockholders’ Agent may reasonably require to review the Earnout Statement, including the relevant books, records and documents Castlight, its Affiliates and/or its Representatives prepared or reviewed in preparing such Earnout Statement, subject, in every instance, to the right of Castlight to withhold any documents in order to preserve any legal privilege associated with such document, including the attorney-client privilege and the work product doctrine. In addition, Castlight shall provide the Stockholders’ Agent and its advisors with reasonable access during regular business hours to employees of Castlight and the Surviving Entity reasonably necessary to complete its review of such Earnout Statement.

(c)

Within 20 Business Days following delivery to the Stockholders’ Agent of the Earnout Statement, the Stockholders’ Agent shall deliver a notice to Castlight of any item or items that the Stockholders’ Agent wishes to dispute (the “Earnout Objection Notice”), together with supporting documentation, information and calculations, including the Stockholders’ Agent’s calculation of any disputed element of the Earnout Statement; provided that any final and binding attribution of fees pursuant to subsection (iii) of the definition of “New Bookings” or the definition of “Stipulated Value” may not be the subject of dispute, including in the Earnout Objection Notice. Any matters not expressly set forth in the Earnout Objection Notice shall be deemed to have been accepted by the Stockholders’ Agent on behalf of the Earnout Participants. If, by the expiration of such 20 Business Day period, the Earnout Objection Notice is not delivered to Castlight, or the Stockholders’ Agent has notified Castlight that there are no items that it wishes to dispute, the draft Earnout Statement shall constitute the final Earnout Statement and the amount of Net New Bookings and New Revenue set forth therein shall constitute the Final Net New Bookings and Final New Revenue.

(d)	If, in accordance with Section 1(c), the Earnout Objection Notice is delivered to Castlight:

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(e)

The fees, costs and expenses of the Reviewing Accountant for any review pursuant to this Section 1 shall be paid (i) by Castlight in the event the difference between the Final Net New Bookings and/or Final New Revenue, as applicable, as determined by the Reviewing Accountant pursuant to Section 1(d)(ii) and the Net New Bookings and/or New Revenue, as applicable, set forth in the draft Earnout Statement initially provided by Castlight pursuant to Section 1(b) (such difference, the “Castlight Difference”) is greater than the difference between the Final Net New Bookings and/or Final New Revenue as determined by the Reviewing Accountant pursuant to Section 1(d)(ii) and the Net New Bookings and New Revenue set forth in the Earnout Objection Notice (such difference, the “Stockholders’ Agent’s Difference”), (ii) by the Earnout Participants if the Castlight Difference is less than the Stockholders’ Agent’s Difference or (iii) equally by Castlight on the one hand, and the Earnout Participant on the other hand, if the Castlight Difference is the same as the Stockholders’ Agent’s Difference. Payment by the Earnout Participants shall, to the maximum extent possible, be made via reduction in the Bookings Earnout Payment and Revenue Earnout Payment otherwise payable to the Earnout Participants (based on the Castlight Stock Price).

2.

Earnout Payments. Within five Business Days following the determination of Final Net New Bookings and Final New Revenue in accordance with Section 1, subject to any reductions pursuant to Castlight’s Set-Off Right in accordance with Article IX of the Agreement for Indemnifiable Damages determined to be owed to an Indemnified Person at such time pursuant to the procedures in such Article IX, Castlight shall deposit the applicable portion of the Earnout Payments, if any, payable to the Earnout Participants with the Exchange Agent and shall instruct the Exchange Agent to pay to each Earnout Participant such Earnout Participant’s Earnout Pro Rata Share of the Earnout Payments.

3.

Castlight Obligations Regarding Earnout Payments. Notwithstanding anything to the contrary contained herein, in no event will Castlight be required to operate the Jiff Business following the Effective Time in any way so as to prioritize the generation of Net New Bookings and/or New Revenue or full payout of the Earnout Payments over other activities that Castlight in its commercially reasonable business judgment believes will advance the interests of and/or increase the value of the business of Castlight, taken as a whole; provided that likewise Castlight will not intentionally discriminate in favor of its legacy business to the detriment of the Jiff Business. Subject to the requirements of the preceding sentence, Castlight shall use its

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4.

Castlight Change of Control or Divestiture. To the extent there is a Castlight Change of Control or a Castlight Divestiture, the Earnout Payments will accelerate and become due and payable unless (a) Castlight or the Jiff Product or Jiff Business, as applicable, is acquired by a publicly-traded entity (the “New Acquirer”), (b) the Earnout Payments obligations are assumed by the New Acquirer and (c) if Mr. Newell is an employee of Castlight at the time of the Castlight Change of Control or Castlight Divestiture, Mr. Newell is offered an opportunity to retain operational control over the sales and marketing, professional services (including the implementations and customer success teams) and research and development organizations (the “Specified Business Functions”) with respect to the Jiff Products or Jiff Business. Castlight agrees that during FY2017 it will not agree to (or publicly announce an intention to effect) a divestiture of some, but not all, Jiff Products.

5.

Tax Treatment of the Earnout Payments. The parties agree that, for U.S. federal income Tax purposes, the Earnout Payments paid under this Annex A are intended to be treated as consideration for shares of Jiff Capital Stock. Shares of Castlight Class B Common Stock issuable pursuant to this Annex A shall be treated by Castlight as issued and outstanding stock of Castlight and the Earnout Participants shall be shown as the registered owners of such shares on the certificate(s) evidence such shares (if such shares are certificated).

6.	Certain Definitions:

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(i)	If the customer under a 2017 Jiff Contract is purchasing only Jiff Products, then the non-contingent professional services fees and subscription fees payable during the first 12 months of such agreement shall be considered attributable to Jiff Products.

(ii)

If the customer under a 2017 Jiff Contract is purchasing both Jiff Products and Castlight Products, then regardless of any specific pricing per product set forth in such 2017 Jiff Contract, it is agreed that for purposes of calculating New Bookings under this Agreement, the non-contingent professional services fees and subscription fees payable during the first 12 months of such agreement shall be apportioned between the Jiff Products and the Castlight

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(iii)

Notwithstanding the foregoing clauses (i) and (ii), if a 2017 Jiff Contract meets the definition of a Jiff CS Giveaway Contract, then regardless of the express pricing, if any, for Jiff Products stated in such contract, the amount of New Bookings deemed attributable to such 2017 Jiff Contract will be (x) 12 times the Stipulated Value for the Jiff Products subject to the contract multiplied by (y) the number of lives eligible to use Jiff Products under such contract; provided that, unless Mr. Newell and the chief executive officer of Castlight agree otherwise in writing, for purposes of calculating New Bookings and determining the amount of Earnout Payments, no more than $2,000,000 of New Bookings shall be attributable to Jiff CS Giveaway Contracts.

7.	Cross References. Unless otherwise specifically set forth herein, all section and subsection references in this Annex A shall be to sections or subsections of this Annex A.

8.	Capitalized Terms. Unless otherwise defined herein, capitalized terms shall have the meanings as set forth in the Agreement.

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(i)	reviewed the financial terms and conditions of the Transaction as reflected in an execution version, provided to us on January 4, 2017, of the Agreement;

(ii)	reviewed certain publicly available historical business and financial information relating to Castlight and certain historical business and financial information relating to Jiff, including public filings of Castlight and historical market prices for Castlight Class B Common Stock;

(iii)

reviewed certain financial information relating to Castlight and Jiff, including certain internal financial forecasts, estimates and other financial and operating data relating to Castlight prepared by the management of Castlight for the fiscal years ending December 31, 2016 and December 31, 2017, and certain financial forecasts, estimates and other financial and operating data relating to Jiff prepared by the management of Jiff, as adjusted by the management of Castlight, for the fiscal years ending December 31, 2016 through December 31, 2019;

(iv)	held discussions with the managements of Castlight and Jiff relating to the past and current operations and financial condition and prospects of Castlight and Jiff;

(v)	held discussions with the management of Castlight as to the strategic rationale for, and certain contemplated benefits (including potential cost savings and revenue enhancements) expected by the management of Castlight to result from, the Transaction;

(vi)	reviewed and analyzed certain publicly available information, including certain stock market data and financial information, relating to selected companies with businesses that we deemed generally relevant in evaluating Castlight and Jiff;

(vii)	reviewed certain publicly available financial information relating to selected transactions that we deemed generally relevant in evaluating the Transaction;

(viii)	reviewed the relative contributions of Castlight and Jiff to certain financial metrics of the pro forma combined company based on the internal financial forecasts, estimates and other financial and operating data of Castlight and Jiff referred to above; and

(ix)	conducted such other financial analyses and investigations as we deemed necessary or appropriate for purposes of the opinion expressed herein.

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