EX-10.1



 Exhibit 10.1 

INDEMNITY AGREEMENT 
 This
Indemnity Agreement, dated as of                     , 2014 is made by and between Castlight Health, Inc., a Delaware corporation (the
“Company”), and                     , a director, officer or key employee of the Company or one of the Company’s
subsidiaries or other service provider who satisfies the definition of Indemnifiable Person set forth below (“Indemnitee”). 

RECITALS 
 A. The Company is
aware that competent and experienced persons are increasingly reluctant to serve as representatives of corporations unless they are protected by comprehensive liability insurance and indemnification, due to increased exposure to litigation costs and
risks resulting from their service to such corporations, and due to the fact that the exposure frequently bears no relationship to the compensation of such representatives; 

B. The members of the Board of Directors of the Company (the “Board”) have concluded that to retain and attract
talented and experienced individuals to serve as representatives of the Company and its Subsidiaries and Affiliates and to encourage such individuals to take the business risks necessary for the success of the Company and its Subsidiaries and
Affiliates, it is necessary for the Company to contractually indemnify certain of its representatives and the representatives of its Subsidiaries and Affiliates, and to assume for itself maximum liability for Expenses and Other Liabilities in
connection with claims against such representatives in connection with their service to the Company and its Subsidiaries and Affiliates; 

C. Section 145 of the Delaware General Corporation Law (“Section 145”), empowers the Company to indemnify by
agreement its officers, directors, employees and agents, and persons who serve, at the request of the Company, as directors, officers, employees or agents of other corporations, partnerships, joint ventures, trusts or other enterprises, and
expressly provides that the indemnification provided thereby is not exclusive; and 
 D. The Company desires and has requested Indemnitee to
serve or continue to serve as a representative of the Company and/or the Subsidiaries or Affiliates of the Company free from undue concern about inappropriate claims for damages arising out of or related to such services to the Company and/or the
Subsidiaries or Affiliates of the Company. 
 AGREEMENT 

NOW, THEREFORE, the parties hereto, intending to be legally bound, hereby agree as follows: 

1. Definitions. 

(a) Affiliate. For purposes of this Agreement, “Affiliate” of the Company means any corporation, partnership,
limited liability company, joint venture, trust or other enterprise in respect of which Indemnitee is or was or will be serving as a director, officer, 







 
trustee, manager, member, partner, employee, agent, attorney, consultant, member of the entity’s governing body (whether constituted as a board of directors, board of managers, general
partner or otherwise), fiduciary, or in any other similar capacity at the request, election or direction of the Company, and including, but not limited to, any employee benefit plan of the Company or a Subsidiary or Affiliate of the Company. 

(b) Change in Control. For purposes of this Agreement, “Change in Control” means (i) any
“person” (as such term is used in Sections 13(d) and 14(d) of the Exchange Act), other than a Subsidiary or a trustee or other fiduciary holding securities under an employee benefit plan of the Company or Subsidiary, is or becomes the
“Beneficial Owner” (as defined in Rule 13d-3 under said Act), directly or indirectly, of securities of the Company representing 30% or more of the total voting power represented by the Company’s then outstanding capital stock, or
(ii) during any period of two consecutive years, individuals who at the beginning of such period constitute the Board and any new director whose election by the Board or nomination for election by the Company’s stockholders was approved by
a vote of at least two-thirds (2/3) of the directors then still in office who either were directors at the beginning of the period or whose election or nomination for election was previously so approved, cease for any reason to constitute a
majority thereof, or (iii) the stockholders of the Company approve a merger or consolidation of the Company with any other corporation, other than a merger or consolidation that would result in the outstanding capital stock of the Company
outstanding immediately prior thereto continuing to represent (either by remaining outstanding or by being converted into capital stock of the surviving entity) at least 70% of the total voting power represented by the capital stock of the Company
or such surviving entity outstanding immediately after such merger or consolidation, or the stockholders of the Company approve a plan of complete liquidation of the Company or an agreement for the sale or disposition by the Company (in one
transaction or a series of transactions) of all or substantially all of the Company’s assets. 
 (c) Expenses.
For purposes of this Agreement, “Expenses” means all direct and indirect costs of any type or nature whatsoever (including, without limitation, all attorneys’ fees and related disbursements, and other out-of-pocket costs), paid or
incurred by Indemnitee in connection with either the investigation, defense or appeal of, or being a witness in, a Proceeding (as defined below), or establishing or enforcing a right to indemnification under this Agreement, Section 145 or
otherwise; provided, however, that Expenses shall not include any judgments, fines, excise taxes or penalties in respect of the Employee Retirement Income Security Act (“ERISA”) or amounts paid in settlement of a Proceeding.

 (d) Exchange Act. For purposes of this Agreement, “Exchange Act” means the Securities Exchange Act of
1934, as amended. 
 (e) Indemnifiable Event. For purposes of this Agreement, “Indemnifiable Event” means
any event or occurrence related to Indemnitee’s service for the Company or any Subsidiary or Affiliate as an Indemnifiable Person (as defined below), or by reason of anything done or not done, or any act or omission, by Indemnitee in any such
capacity. 
 (f) Indemnifiable Person. For the purposes of this Agreement, “Indemnifiable Person” means any
person who is or was a director, officer, trustee, manager, member, partner, employee, attorney, consultant, member of an entity’s governing body (whether constituted as a board of directors, board of managers, general partner or otherwise) or
other agent or fiduciary of the Company or a Subsidiary or Affiliate of the Company. 

  
 2 








 (g) Independent Counsel. For purposes of this Agreement, “Independent
Counsel” means legal counsel that has not performed services for the Company or Indemnitee in the five years preceding the time in question and that would not, under applicable standards of professional conduct, have a conflict of interest in
representing either the Company or Indemnitee. 
 (h) Other Liabilities. For purposes of this Agreement, “Other
Liabilities” means any and all liabilities of any type whatsoever (including, but not limited to, judgments, fines, penalties, ERISA (or other benefit plan related) excise taxes or penalties, and amounts paid in settlement and all interest,
taxes, assessments and other charges paid or payable in connection with or in respect of any such judgments, fines, ERISA (or other benefit plan related) excise taxes or penalties, or amounts paid in settlement). 

(i) Proceeding. For the purposes of this Agreement, “Proceeding” means any threatened, pending, or completed
action, suit or other proceeding, whether civil, criminal, administrative, investigative, legislative or any other type whatsoever, preliminary, informal or formal, including any arbitration or other alternative dispute resolution and including any
appeal of any of the foregoing. 
 (j) Subsidiary. For purposes of this Agreement, “Subsidiary” means any
entity of which more than 50% of the outstanding voting securities is owned directly or indirectly by the Company. 
 2. Agreement to
Serve. The Indemnitee agrees to serve and/or continue to serve as an Indemnifiable Person in the capacity or capacities in which Indemnitee currently serves the Company as an Indemnifiable Person, and any additional capacity in which Indemnitee
may agree to serve, until such time as Indemnitee’s service in a particular capacity shall end according to the terms of an agreement, the Company’s Certificate of Incorporation or Bylaws, governing law, or otherwise. Nothing contained in
this Agreement is intended to create any right to continued employment or other form of service for the Company or a Subsidiary or Affiliate of the Company by Indemnitee. 

3. Mandatory Indemnification. 

(a) Agreement to Indemnify. In the event Indemnitee is a person who was or is a party to or witness in or is threatened
to be made a party to or witness in any Proceeding by reason of an Indemnifiable Event, the Company shall indemnify Indemnitee from and against any and all Expenses and Other Liabilities incurred by Indemnitee in connection with (including in
preparation for) such Proceeding to the fullest extent not prohibited by the provisions of the Delaware General Corporation Law (“DGCL”), as the same may be amended from time to time (but only to the extent that such
amendment permits the Company to provide broader indemnification rights than the DGCL permitted prior to the adoption of such amendment). 

  
 3 








 (b) Exception for Amounts Covered by Insurance and Other Sources.
Notwithstanding the foregoing, the Company shall not be obligated to indemnify Indemnitee for Expenses or Other Liabilities of any type whatsoever (including, but not limited to judgments, fines, penalties, ERISA excise taxes or penalties and
amounts paid in settlement) to the extent such have been paid directly to Indemnitee (or paid directly to a third party on Indemnitee’s behalf) by any directors and officers, or other type, of insurance maintained by the Company. Further,
[except as provided in Section 3(c),] the Company shall not be obligated to indemnify Indemnitee for Expenses or Other Liabilities of any type whatsoever (including, but not limited to judgments, fines, penalties, ERISA excise taxes or
penalties and amounts paid in settlement) to the extent such have been paid directly to Indemnitee (or paid directly to a third party on Indemnitee’s behalf) pursuant to any indemnification arrangement for the benefit of Indemnitee provided by
any third party; provided however that this provision shall not limit any such third party’s equitable rights to contribution or indemnification from the Company with respect to amounts so paid by the third party. 

(c) [Company Obligations Primary. The Company hereby acknowledges that Indemnitee has or may from time to time
obtain certain rights to indemnification for or advancement of Expenses and Other Liabilities and/or insurance provided by [name of VC or other sponsoring organization] (“Other Indemnitor”). The Company agrees with Indemnitee
that the Company is the indemnitor of first resort of Indemnitee with respect to matters for which indemnification is provided under this Agreement (i.e., its obligations to Indemnitee are primary and any obligation of the Other Indemnitor to
advance of expenses or to provide indemnification for the same expenses or liabilities incurred by Indemnitee are secondary) and that the Company will be obligated to make all payments due to or for the benefit of Indemnitee under this Agreement
without regard to any rights that Indemnitee may have against the Other Indemnitor. The Company hereby waives any equitable rights to contribution or indemnification from the Other Indemnitor in respect of any amounts paid to Indemnitee hereunder.
The Company further agrees that no reimbursement of Other Liabilities or payment of Expenses by the Other Indemnitor to or for the benefit of Indemnitee shall affect the obligations of the Company hereunder, and that the Company shall be obligated
to repay the Other Indemnitor for all amounts so paid or reimbursed to the extent that the Company has an obligation to indemnify Indemnitee for such Expenses or Other Liabilities hereunder. In the event that the Company provides any such repayment
to the Other Indemnitor, the Company shall not be obligated to reimburse the Indemnitee for any Expenses or Other Liabilities related to such repayments. The Company will not assert that the Indemnitee must seek expense advancement or reimbursement,
or indemnification, from the Other Indemnitor before the Company must perform its expense advancement and reimbursement, and indemnification obligations, under this Agreement. No advancement or payment by the Other Indemnitor on behalf of Indemnitee
with respect to any claim for which Indemnitee has sought indemnification from the Company shall affect the foregoing. The Other Indemnitor shall be subrogated to the extent of such advancement or payment to all of the rights of recovery which
Indemnitee would have had against the Company if the Other Indemnitor had not advanced or paid any amount to or on behalf of Indemnitee. If for any reason a court of competent jurisdiction determines that the Other Indemnitor is not entitled to the
subrogation rights described in the preceding sentence, the Other Indemnitor shall have the right of contribution by the Company to the Other Indemnitor with respect to any advance or payment by the Other Indemnitor to or on behalf of the
Indemnitee.] 

  
 4 








 4. Partial Indemnification. If Indemnitee is entitled under any provision of this
Agreement to indemnification by the Company for some or a portion of any Expenses or Other Liabilities but not entitled, however, to indemnification for the total amount of such Expenses or Other Liabilities, the Company shall nevertheless indemnify
Indemnitee for such total amount except as to the portion thereof for which indemnification is prohibited by the provisions of the DGCL. In any review or Proceeding to determine the extent of indemnification, the Company shall bear the burden to
establish, by clear and convincing evidence, the lack of a successful resolution of a particular claim, issue or matter and which amounts sought in indemnity are allocable to claims, issues or matters which were not successfully resolved. 

5. Liability Insurance. So long as Indemnitee shall continue to serve the Company or a Subsidiary or Affiliate of the Company as an
Indemnifiable Person and thereafter so long as Indemnitee shall be subject to any possible claim or threatened, pending or completed Proceeding as a result of an Indemnifiable Event, the Company shall use reasonable efforts to maintain in full force
and effect for the benefit of Indemnitee as an insured (i) liability insurance issued by one or more reputable insurers and having the policy amount and deductible deemed appropriate by the Board and providing in all respects coverage at least
comparable to and in the same amount as that provided to the Chairman of the Board or the Chief Executive Officer of the Company and (ii) any replacement or substitute policies issued by one or more reputable insurers providing in all respects
coverage at least comparable to and in the same amount as that being provided to the Chairman of the Board or the Chief Executive Officer of the Company. The purchase, establishment and maintenance of any such insurance or other arrangements shall
not in any way limit or affect the rights and obligations of the Company or of Indemnitee under this Agreement except as expressly provided herein, and the execution and delivery of this Agreement by the Company and Indemnitee shall not in any way
limit or affect the rights and obligations of the Company or the other party or parties thereto under any such insurance or other arrangement. 

6. Mandatory Advancement of Expenses. If requested by Indemnitee, the Company shall advance prior to the final disposition of the
Proceeding all Expenses reasonably incurred by Indemnitee in connection with (including in preparation for) a Proceeding related to an Indemnifiable Event. Indemnitee hereby undertakes to repay such amounts advanced if, and only if and to the extent
that, it shall ultimately be determined that Indemnitee is not entitled to be indemnified by the Company under the provisions of this Agreement, the Company’s Bylaws or the DGCL; it being understood that if Indemnitee is entitled to be
indemnified by the Company under any of this Agreement, the Company’s Bylaws or the DGCL, Indemnitee shall not be required to repay such amounts advanced to the extent they relate to such matter(s) for which Indemnitee is entitled to such
indemnification. The advances to be made hereunder shall be paid by the Company to Indemnitee or directly to a third party designated by Indemnitee within thirty (30) days following delivery of a written request therefor by Indemnitee to the
Company. Indemnitee’s undertaking to repay any Expenses advanced to Indemnitee hereunder shall be unsecured and shall not be subject to the accrual or payment of any interest thereon. 

7. Notice and Other Indemnification Procedures. 

(a) Notification. Promptly after receipt by Indemnitee of notice of the commencement of or the threat of commencement of
any Proceeding, Indemnitee shall, if Indemnitee believes that indemnification or advancement of Expenses with respect thereto may 

  
 5 








 
be sought from the Company under this Agreement, notify the Company of the commencement or threat of commencement thereof. However, a failure so to notify the Company promptly following
Indemnitee’s receipt of such notice shall not relieve the Company from any liability that it may have to Indemnitee except to the extent that the Company is materially prejudiced in its defense of such Proceeding as a result of such failure.

 (b) Insurance and Other Matters. If, at the time of the receipt of a notice of the commencement of a Proceeding
pursuant to Section 7(a) above, the Company has director and officer liability insurance in effect, the Company shall give prompt notice of the commencement of such Proceeding to the issuers in accordance with the procedures set forth in the
respective policies. The Company shall thereafter take all reasonable action to cause such insurers to pay, on behalf of Indemnitee, all amounts payable as a result of such Proceeding in accordance with the terms of such insurance policies. 

(c) Assumption of Defense. In the event the Company shall be obligated to advance the Expenses for any Proceeding
against Indemnitee, the Company, if deemed appropriate by the Company, shall be entitled to assume the defense of such Proceeding as provided herein. Such defense by the Company may include the representation of two or more parties by one attorney
or law firm as permitted under the ethical rules and legal requirements related to joint representations. Following delivery of written notice to Indemnitee of the Company’s election to assume the defense of such Proceeding, the approval by
Indemnitee (which approval shall not be unreasonably withheld, conditioned or delayed) of counsel designated by the Company and the retention of such counsel by the Company, the Company will not be liable to Indemnitee under this Agreement for any
fees and expenses of counsel subsequently incurred by Indemnitee with respect to the same Proceeding. If (i) the employment of counsel by Indemnitee has been previously authorized by the Company, (ii) Indemnitee shall have notified the
Board in writing that Indemnitee has reasonably concluded that there is likely to be a conflict of interest between the Company and Indemnitee in the conduct of any such defense, or (iii) the Company fails to employ counsel to assume the
defense of such Proceeding, the fees and expenses of Indemnitee’s counsel shall be subject to indemnification and/or advancement pursuant to the terms of this Agreement. Nothing herein shall prevent Indemnitee from employing counsel for any
such Proceeding at Indemnitee’s expense. 
 (d) Settlement. The Company shall not be liable to indemnify
Indemnitee under this Agreement or otherwise for any amounts paid in settlement of any Proceeding effected without the Company’s written consent; provided, however, that if a Change in Control has occurred, the Company shall be
liable for indemnification of Indemnitee for amounts paid in settlement if the Independent Counsel (selected in accordance with Section 8(c) below) has approved the settlement. Neither the Company nor any Subsidiary or Affiliate shall enter
into a settlement of any Proceeding that might result in the imposition of any Expense, Other Liability, penalty, limitation or detriment on Indemnitee, whether indemnifiable under this Agreement or otherwise, without Indemnitee’s written
consent, unless such settlement is purely monetary, fully releases Indemnitee of all liability associated with such Proceeding and has been consented to by the Independent Directors. Neither the Company nor Indemnitee shall unreasonably withhold
consent from any settlement of any Proceeding. The Company shall not, on its own behalf, settle any part of any Proceeding to which Indemnitee is party with respect to other parties (including the Company) without the written consent of Indemnitee
if any portion of such settlement is to be funded from insurance proceeds from insurance policies as to which Indemnitee is an insured party unless approved by either (i) the written consent of Indemnitee or (ii) a majority of the
Independent Directors; provided, however, that the right to constrain the Company’s use of corporate insurance as described in this section shall terminate at the time the Company concludes (per the terms of this Agreement) that
(x) Indemnitee is not entitled to indemnification pursuant to this Agreement, or (y) such indemnification obligation to Indemnitee has been fully discharged by the Company. 

  
 6 








 8. Determination of Right to Indemnification. 

(a) Success on the Merits or Otherwise. To the extent that Indemnitee has been successful on the merits or otherwise in
defense of any Proceeding referred to in Section 3(a) above or in the defense of any claim, issue or matter described therein, the Company shall indemnify Indemnitee against Expenses actually and reasonably incurred in connection therewith.

 (b) Indemnification in Other Situations. In the event that Section 8(a) is inapplicable, the Company shall
also indemnify Indemnitee if Indemnitee has not failed to meet the applicable standard of conduct for indemnification, as determined by the process set forth in Sections 8(c) and 8(d) below. 

(c) Forum. Indemnitee shall be entitled to select the forum in which determination of whether or not Indemnitee has met
the applicable standard of conduct shall be decided, and such election will be made from among the following: 
 (1) Those
members of the Board who are Independent Directors even though less than a quorum; 
 (2) A committee of Independent
Directors designated by a majority vote of Independent Directors, even though less than a quorum; or 
 (3) Independent
Counsel selected by Indemnitee and approved by the Board, which approval may not be unreasonably withheld, conditioned or delayed, which counsel shall make such determination in a written opinion. 

If Indemnitee is an officer or a director of the Company at the time that Indemnitee is selecting the forum, then Indemnitee
shall not select Independent Counsel as such forum unless there are no Independent Directors or unless the Independent Directors agree to the selection of Independent Counsel as the forum. 

The selected forum shall be referred to herein as the “Reviewing Party”. Notwithstanding the foregoing, following any Change in Control, the
Reviewing Party shall be Independent Counsel selected in the manner provided in (3) above. 
 (d) Decision Timing and
Expenses. As soon as practicable, and in no event later than thirty (30) days after receipt by the Company of written notice of Indemnitee’s choice of forum pursuant to Section 8(c) above, the Company and Indemnitee shall each
submit to the Reviewing Party such information as they believe is appropriate for the Reviewing Party to consider. The Reviewing Party shall arrive at its decision within a reasonable period of time 


  
 7 








 
following the receipt of all such information from the Company and Indemnitee, but in no event later than thirty (30) days following the receipt of all such information, provided that the
time by which the Reviewing Party must reach a decision may be extended by mutual agreement of the Company and Indemnitee. All Expenses associated with the process set forth in this Section 8(d), including but not limited to the Expenses of the
Reviewing Party, shall be paid by the Company. 
 (e) Delaware Court of Chancery. Notwithstanding a final
determination by any Reviewing Party that Indemnitee is not entitled to indemnification with respect to a specific Proceeding, Indemnitee shall have the right to apply to the Court of Chancery, for the purpose of enforcing Indemnitee’s right to
indemnification pursuant to this Agreement; it being understood that the Court of Chancery shall be the exclusive forum for enforcing Indemnitee’s right to indemnification pursuant to this Agreement following the determination by the Reviewing
Party. 
 (f) Expenses. The Company shall indemnify Indemnitee against all Expenses incurred by Indemnitee in
connection with any hearing or Proceeding under this Section 8 involving Indemnitee and against all Expenses and Other Liabilities incurred by Indemnitee in connection with any other Proceeding between the Company and Indemnitee involving the
interpretation or enforcement of the rights of Indemnitee under this Agreement unless a court of competent jurisdiction finds that each of the material claims of Indemnitee in any such Proceeding was frivolous or made in bad faith. 

(g) Determination of “Good Faith”. For purposes of any determination of whether Indemnitee acted in “good
faith,” Indemnitee shall be deemed to have acted in good faith if in taking or failing to take the action in question Indemnitee relied on the records or books of account of the Company or a Subsidiary or Affiliate, including financial
statements, or on information, opinions, reports or statements provided to Indemnitee by the officers or other employees of the Company or a Subsidiary or Affiliate in the course of their duties, or on the advice of legal counsel for the Company or
a Subsidiary or Affiliate, or on information or records given or reports made to the Company or a Subsidiary or Affiliate by an independent certified public accountant or by an appraiser or other expert selected by the Company or a Subsidiary or
Affiliate, or by any other person (including legal counsel, accountants and financial advisors) as to matters Indemnitee reasonably believes are within such other person’s professional or expert competence and who has been selected with
reasonable care by or on behalf of the Company or a Subsidiary or Affiliate. In connection with any determination as to whether Indemnitee is entitled to be indemnified hereunder, or to advancement of expenses, the Reviewing Party or court shall
presume that Indemnitee has satisfied the applicable standard of conduct and is entitled to indemnification or advancement of Expenses, as the case may be, and the burden of proof shall be on the Company to establish, by clear and convincing
evidence, that Indemnitee is not so entitled. The provisions of this Section 8(g) shall not be deemed to be exclusive or to limit in any way the other circumstances in which Indemnitee may be deemed to have met the applicable standard of
conduct set forth in this Agreement. In addition, the knowledge and/or actions, or failures to act, of any other person serving the Company or a Subsidiary or Affiliate as an Indemnifiable Person shall not be imputed to Indemnitee for purposes of
determining the right to indemnification hereunder. 

  
 8 








 9. Exceptions. Any other provision herein to the contrary notwithstanding, 

(a) Claims Initiated by Indemnitee. The Company shall not be obligated pursuant to the terms of this Agreement to
indemnify or advance Expenses to Indemnitee with respect to Proceedings or claims initiated or brought voluntarily by Indemnitee and not by way of defense, except (i) with respect to Proceedings brought to establish or enforce a right to
indemnification under this Agreement, any other statute or law, as permitted under Section 145, or otherwise, (ii) where the Board has consented to the initiation of such Proceeding, or (iii) with respect to Proceedings brought to
discharge Indemnitee’s fiduciary responsibilities, whether under ERISA or otherwise, but such indemnification or advancement of Expenses may be provided by the Company in specific cases if the Board finds it to be appropriate; provided that
these exceptions shall not apply to Proceedings in which Indemnitee is engaged in conduct protected by any whistleblower statute, the up-the-ladder provisions of
Section 307 of the Sarbanes-Oxley Act of 2002 (the “Sarbanes-Oxley Act”), or any similar provision of any applicable federal, state or
foreign securities law; or 
 (b) Section 16(b) Actions. The Company shall not be obligated pursuant to the
terms of this Agreement to indemnify Indemnitee on account of any suit in which judgment is rendered against Indemnitee for an accounting of profits made from the purchase or sale by Indemnitee of securities of the Company pursuant to the provisions
of Section 16(b) of the Securities Exchange Act of l934 (the “Exchange Act”) and amendments thereto or similar provisions of any federal, state or local statutory law; or 

(c) Exchange Act Reimbursement. The Company shall not be obligated pursuant to the terms of this Agreement to indemnify
Indemnitee on account of any reimbursement of the Company by the Indemnitee of any bonus or other incentive-based or equity-based compensation or of any profits realized
by the Indemnitee from the sale of securities of the Company, as required in each case under the Exchange Act (including any such reimbursements that arise from an accounting restatement of the Company pursuant to Section 304 of the Sarbanes-Oxley Act or Section 954 of the Dodd Frank Wall Street Reform and Consumer Protection Act (“Dodd Frank Act”), or the payment to the Company of profits arising from the purchase
and sale by Indemnitee of securities in violation of Section 306 of the Sarbanes-Oxley Act); or 

(d) Unlawful Indemnification. The Company shall not be obligated pursuant to the terms of this Agreement to indemnify
Indemnitee for Other Liabilities if such indemnification is prohibited by law, if so established by a non-appealable judgment or other final non-appealable adjudication
adverse to Indemnitee. 
 Notwithstanding any of the foregoing, (i) Indemnitee is entitled to receive advancement of Expenses for the defense of any
Proceeding referenced in subsections (b) or (c) above; and (ii) if Indemnitee is required to make a payment in a Proceeding described in subsection (c), and no court in any such Proceeding has found that Indemnitee personally
engaged in acts or omissions outside the scope of indemnification, Indemnitee shall not be required to repay such advancement of Expenses. 

10. Non-exclusivity. The provisions for indemnification and advancement of Expenses set forth in this Agreement shall not be deemed
exclusive of any other rights which Indemnitee may have under any provision of law, the Company’s Certificate of Incorporation or Bylaws, the vote of the Company’s stockholders or disinterested directors, other agreements, or


  
 9 








 
otherwise, both as to acts or omissions in his or her official capacity and to acts or omissions in another capacity while serving the Company or a Subsidiary or Affiliate as an Indemnifiable
Person and Indemnitee’s rights hereunder shall continue after Indemnitee has ceased serving the Company or a Subsidiary or Affiliate as an Indemnifiable Person and shall inure to the benefit of the heirs, executors and administrators of
Indemnitee. 
 11. Severability. If any provision or provisions of this Agreement shall be held to be invalid, illegal or
unenforceable for any reason whatsoever, (i) the validity, legality and enforceability of the remaining provisions of the Agreement (including, without limitation, all portions of any paragraphs of this Agreement containing any such provision
held to be invalid, illegal or unenforceable, that are not themselves invalid, illegal or unenforceable) shall not in any way be affected or impaired thereby, and (ii) to the fullest extent possible, the provisions of this Agreement (including,
without limitation, all portions of any paragraphs of this Agreement containing any such provision held to be invalid, illegal or unenforceable, that are not themselves invalid, illegal or unenforceable) shall be construed so as to give effect to
the intent manifested by the provision held invalid, illegal or unenforceable. 
 12. Modification and Waiver. No supplement,
modification or amendment of this Agreement shall be binding unless executed in writing by both of the parties hereto. No waiver of any of the provisions of this Agreement shall be deemed or shall constitute a waiver of any other provision hereof
(whether or not similar) and except as expressly provided herein, no such waiver shall constitute a continuing waiver. 
 13. Successors
and Assigns. This Agreement shall be binding upon and inure to the benefit of and be enforceable by the parties hereto and their respective successors (including any direct or indirect successor by purchase, merger, consolidation or otherwise to
all or substantially all of the business and/or assets of the Company), assigns, spouses, heirs and personal and legal representatives. The Company shall require and cause any successor (whether direct or indirect by purchase, merger, consolidation
or otherwise) to all, substantially all, or a substantial part, of the business and/or assets of the Company, by written agreement in form and substance satisfactory to Indemnitee, expressly to assume and agree to perform this Agreement in the same
manner and to the same extent that the Company would be required to perform if no such succession had taken place. In the event of a Change in Control, the Company shall maintain in force any and all directors’ and officers’ liability
insurance policies and fiduciary liability insurance policies then maintained by the Company in a manner that will continue to provide coverage to the individual insureds under these policies for a period of six years after such Change of Control.

 14. Notice. All notices, requests, demands and other communications under this Agreement shall be in writing and shall be deemed
duly given (i) if delivered by hand and a receipt is provided by the party to whom such communication is delivered, (ii) if mailed by certified or registered mail with postage prepaid, return receipt requested, on the signing by the
recipient of an acknowledgement of receipt form accompanying delivery through the U.S. mail, (iii) personal service by a process server, or (iv) delivery to the recipient’s address by overnight delivery (e.g., FedEx, UPS or DHL) or
other commercial delivery service. Addresses for notice to either party are as shown on the signature page of this Agreement, or as subsequently modified by written notice complying with the provisions of this Section 14. Delivery of
communications to the Company with respect to this Agreement shall be sent to the attention of the Company’s General Counsel. 

  
 10 








 15. No Presumptions. For purposes of this Agreement, the termination of any Proceeding, by
judgment, order, settlement (whether with or without court approval) or conviction, or upon a plea of nolo contendere or its equivalent, shall not, of itself, create a presumption that Indemnitee did not meet any particular standard of conduct or
have any particular belief or that a court has determined that indemnification is not permitted by applicable law or otherwise. In addition, neither the failure of the Company or a Reviewing Party to have made a determination as to whether
Indemnitee has met any particular standard of conduct or had any particular belief, nor an actual determination by the Company or a Reviewing Party that Indemnitee has not met such standard of conduct or did not have such belief, prior to the
commencement of Proceedings by Indemnitee to secure a judicial determination by exercising Indemnitee’s rights under Section 8(e) of this Agreement shall be a defense to Indemnitee’s claim or create a presumption that Indemnitee has
failed to meet any particular standard of conduct or did not have any particular belief or is not entitled to indemnification under applicable law or otherwise. Additionally, any admission of liability by the Company in connection with any
settlement by the Company with a regulatory agency shall not, of itself, create a presumption that Indemnitee did not meet any particular standard of conduct or have any particular belief or that a court has determined that indemnification is not
permitted by applicable law or otherwise. Moreover, the conviction of or plea of guilty or nolo contendere (or its equivalent) by Indemnitee in a jurisdiction outside the United States and its territories, shall not, of itself, create a presumption
that Indemnitee did not meet any particular standard of conduct or have any particular belief or that a court has determined that indemnification is not permitted by applicable law or otherwise, unless the underlying act or omission relating to such
conviction or plea would be deemed a criminal offense within the United States and its territories or any subdivision thereof having jurisdiction over Indemnitee. 

16. Survival of Rights. The rights conferred on Indemnitee by this Agreement shall continue after Indemnitee has ceased to serve the
Company or a Subsidiary or Affiliate of the Company as an Indemnifiable Person and shall inure to the benefit of Indemnitee’s heirs, executors and administrators. 

17. Subrogation and Contribution. 

(a) [Except as provided in Section 3(c),] in the event of payment under this Agreement, the Company shall be
subrogated to the extent of such payment to all of the rights of recovery of Indemnitee, who shall execute all documents required and shall do all acts that may be necessary to secure such rights and to enable the Company effectively to bring suit
to enforce such rights. 
 (b) To the fullest extent permissible under applicable law, if the indemnification provided for in
this Agreement is unavailable to Indemnitee for any reason whatsoever, the Company, in lieu of indemnifying Indemnitee, shall contribute to the amount incurred by or on behalf of Indemnitee, whether for judgments, fines, penalties, excise taxes,
amounts paid or to be paid in settlement and/or for Expenses, in connection with any claim relating to an indemnifiable event under this Agreement, in such proportion as is deemed fair and reasonable in light of all of the circumstances of such
Proceeding in order to reflect (i) the 

  
 11 








 
relative benefits received by the Company and Indemnitee as a result of the event(s) and/or transaction(s) giving cause to such Proceeding; and/or (ii) the relative fault of the Company (and
its directors, officers, employees and agents) and Indemnitee in connection with such event(s) and/or transaction(s). 
 18. Specific
Performance, Etc. The parties recognize that if any provision of this Agreement is violated by the Company, Indemnitee may be without an adequate remedy at law. Accordingly, in the event of any such violation, Indemnitee shall be entitled, if
Indemnitee so elects, to institute Proceedings, either in law or at equity, to obtain damages, to enforce specific performance, to enjoin such violation, or to obtain any relief or any combination of the foregoing as Indemnitee may elect to pursue.

 19. Counterparts. This Agreement may be executed in counterparts, each of which shall for all purposes be deemed to be an original
but all of which together shall constitute one and the same agreement. Only one such counterpart signed by the party against whom enforceability is sought needs to be produced to evidence the existence of this Agreement. 

20. Headings. The headings of the sections and paragraphs of this Agreement are inserted for convenience only and shall not be deemed
to constitute part of this Agreement or to affect the construction or interpretation thereof. 
 21. Governing Law. This Agreement
shall be governed exclusively by and construed according to the laws of the State of Delaware, as applied to contracts between Delaware residents entered into and to be performed entirely with Delaware. 

22. Consent to Jurisdiction. The Company and Indemnitee each hereby irrevocably consent to the jurisdiction of the courts of the State
of Delaware for all purposes in connection with any Proceeding which arises out of or relates to this Agreement. 
 23. Effective
Date. This Agreement shall become effective on the closing date of the Company’s initial public offering pursuant to a Registration Statement on Form S-1 (the “Effective Date”). 

24. Entire Agreement. This Agreement and the documents referred to herein constitute the entire agreement and understanding of the
parties with respect to the subject matter of this Agreement, and, upon the Effective Date, this Agreement and the documents referred to herein supersede any and all prior understandings and agreements, whether oral or written, between or among the
parties hereto with respect to the specific subject matter hereof. 

  
 12 








 The parties hereto have entered into this Indemnity Agreement effective as of the date first above written. 

 

									
		 		 	CASTLIGHT HEALTH, INC.
					
		 		 		 	By:	 	 
					
		 		 		 	Its:	 	 
				
		 		 		 	INDEMNITEE:
				
		 		 		 	 
				
		 		 	Address:    	 	 
				
		 		 		 	 


  
 13