EX-10.4



 Exhibit 10.4 

CASTLIGHT HEALTH, INC. 

2014 EMPLOYEE STOCK PURCHASE PLAN 

1. Establishment of Plan. Castlight Health, Inc. proposes to grant options to purchase shares of Common Stock to eligible employees of
the Company and its Participating Corporations pursuant to this Plan. The Company intends this Plan to qualify as an “employee stock purchase plan” under Code Section 423 (including any amendments to or replacements of such Section),
and this Plan shall be so construed. Any term not expressly defined in this Plan but defined for purposes of Code Section 423 shall have the same definition herein. However, with regard to offers of options for purchase of the Common Stock
under the Plan to employees outside the United States working for a Subsidiary or an Affiliate, the Board may offer a subplan or an option that is not intended to meet the Code Section 423 requirements, provided, if necessary under Code
Section 423, that the other terms and conditions of the Plan are met. Subject to Section 14, a total of six million (6,000,000) shares of Common Stock is reserved for issuance under this Plan. 

In addition, on each January 1 for the first nine (9) calendar years after the first Offering Date, the aggregate number of shares of Common Stock
reserved for issuance under the Plan shall be increased automatically by the lesser of (a) the number of shares of Common Stock equal to one percent (1%) of the aggregate number of outstanding shares of Class A and Class B common
stock of the Company on the immediately preceding December 31 (rounded down to the nearest whole share) or (b) such number of Shares determined by the Board; provided, however, that if prior to January 1 of a calendar year, the Board
has not either confirmed the one percent (1%) increase described in clause “(a)” of this paragraph or approved an increase of a lesser number of Shares, then the Board shall be deemed to have waived the automatic increase provided for
by this paragraph, and no such increase shall occur for such calendar year;; and, provided further, that the aggregate number of shares issued over the term of this Plan shall not exceed thirty-six million (36,000,000) shares of Common
Stock. 
 The number of shares reserved for issuance under this Plan and the maximum number of shares that may be issued under this Plan shall be subject to
adjustments effected in accordance with Section 14 of this Plan. Capitalized terms not defined elsewhere in the text are defined in Section 27. 

2. Purpose. The purpose of this Plan is to provide eligible employees of the Company and Participating Corporations with a means of
acquiring an equity interest in the Company through payroll deductions, to enhance such employees’ sense of participation in the affairs of the Company and Participating Corporations, and to provide an incentive for continued employment. 

3. Administration. The Plan will be administered by the Board or the Compensation Committee of the Board (either referred to herein as
the “Committee”). Subject to the provisions of this Plan and the limitations of Section 423 of the Code or any successor provision in the Code, all questions of interpretation or application of this Plan shall be
determined by the Committee and its decisions shall be final and binding upon all Participants. The Committee will 

  
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have full and exclusive discretionary authority to construe, interpret and apply the terms of the Plan, to determine eligibility and decide upon any and all claims filed under the Plan. Every
finding, decision and determination made by the Committee will, to the full extent permitted by law, be final and binding upon all parties. Notwithstanding any provision to the contrary in this Plan, the Committee may adopt rules and/or procedures
relating to the operation and administration of the Plan to accommodate requirements of local law and procedures outside of the United States. The Committee will have the authority to determine the Fair Market Value of the Common Stock (which
determination shall be final, binding and conclusive for all purposes) in accordance with Section 8 below and to interpret Section 8 of the Plan in connection with circumstances that impact the Fair Market Value. Members of the Committee
shall receive no compensation for their services in connection with the administration of this Plan, other than standard fees as established from time to time by the Board for services rendered by Board members serving on the Board or its
committees. All expenses incurred in connection with the administration of this Plan shall be paid by the Company. For purposes of this Plan, the Committee may designate separate offerings under the Plan (the terms of which need not be identical) in
which eligible employees of one or more Participating Corporations will participate, even if the dates of the applicable Offering Periods of each such offering are identical. 

4. Eligibility.  

(a) Any employee of the Company or the Participating Corporations is eligible to participate in an Offering Period under this
Plan except that one or more of the following categories of employees may be excluded from coverage under the Plan by the Committee (other than where prohibited by applicable law): 

(i) employees who are not employed by the Company or a Participating Corporation prior to the beginning of such Offering Period
or prior to such other time period as specified by the Committee; 
 (ii) employees who are customarily employed for twenty
(20) hours or less per week; 
 (iii) employees who are customarily employed for five (5) months or less in a
calendar year; 
 (iv) employees who, together with any other person whose stock would be attributed to such employee
pursuant to Section 424(d) of the Code, own stock or hold options to purchase stock possessing five percent (5%) or more of the total combined voting power or value of all classes of stock of the Company or any of its Participating
Corporations or who, as a result of being granted an option under this Plan with respect to such Offering Period, would own stock or hold options to purchase stock possessing five percent (5%) or more of the total combined voting power or value
of all classes of stock of the Company or any of its Participating Corporations; and 
 (v) employees who do not meet any
other eligibility requirements that the Committee may choose to impose (within the limits permitted by the Code, if applicable); 

  
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 The foregoing notwithstanding, an individual shall not be eligible if his or her participation in
the Plan is prohibited by the law of any country that has jurisdiction over him or her or if he or she is subject to a collective bargaining agreement that does not provide for participation in the Plan. 

(b) Individuals who provide services to the Company or any of its Participating Corporations as independent contractors who are
reclassified as common law employees for any reason except for federal income and employment tax purposes are not eligible to participate in an Offering Period under this Plan. 

5. Offering Dates.  

(a) While the Plan is in effect, the Committee shall determine the duration and commencement date of each Offering Period,
provided that an Offering Period shall in no event be longer than twenty-seven (27) months, except as otherwise provided by an applicable subplan. Offering Periods may be consecutive or overlapping. Each Offering Period may consist of one or
more Purchase Periods during which payroll deductions of Participants are accumulated under this Plan. While the Plan is in effect, the Committee shall determine the duration and commencement date of each Purchase Period, provided that a Purchase
Period shall in no event end later than the close of the Offering Period in which it begins. Purchase Periods shall be consecutive. 

(b) The initial Offering Period shall commence on the Effective Date, and shall end with the Purchase Date that occurs on a
date selected by the Committee approximately six (6) months after the Effective Date (but in any event not more than twenty-seven (27) months after the Effective Date). The initial Offering Period shall consist of a single Purchase Period.
Thereafter, a new six-month Offering Period shall commence on each May 1 and November 1, with each such Offering Period also consisting of a single six-month Purchase Period, except as otherwise provided by an applicable subplan. The
Committee shall have the power to change these terms as provided in Section 25 below. 
 6. Participation in this Plan. 

 (a) Any employee who is an eligible employee determined in accordance with Section 4 immediately prior to the
initial Offering Period will be automatically enrolled in the initial Offering Period under this Plan at a contribution level equal to fifteen percent (15%) of such employee’s Compensation. Notwithstanding the foregoing, an eligible
employee may elect to decrease his or her contribution rate for the initial Offering Period under the Plan by delivering an enrollment/change form to the Company and/or by affecting such decrease through an authorized third party administrator (the
“Third Party Administrator”), within thirty (30) days after the filing of an effective registration statement pursuant to Form S-8, or such shorter time as may be determined by the Committee. 

(b) With respect to Offering Periods after the initial Offering Period, an eligible employee determined in accordance with
Section 4 may elect to become a Participant by submitting an enrollment/change form, or electronic representation thereof, to the Company and/or via the Third Party Administrator’s standard process, prior to the commencement of the
Offering Period to which such agreement relates in accordance with such rules as the Committee may determine. 

  
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 (c) Once an employee becomes a Participant in an Offering Period, then such
Participant will automatically participate in each subsequent Offering Period commencing immediately following the last day of such prior Offering Period at the same contribution level unless the Participant withdraws or is deemed to withdraw from
this Plan or terminates further participation in the Offering Period as set forth in Section 11 below or otherwise notifies the Company of a change in the Participant’s contribution letter by filing an additional subscription agreement or
electronic representation thereof with the Company and/or the Third Party Administrator, prior to the next Offering Period. A Participant that is automatically enrolled in a subsequent Offering Period pursuant to this section is not required to file
any additional subscription agreement in order to continue participation in this Plan. 
 7. Grant of Option on Enrollment. Becoming
a Participant with respect to an Offering Period will constitute the grant (as of the Offering Date) by the Company to such Participant of an option to purchase on the Purchase Date up to that number of shares of Common Stock determined by a
fraction, the numerator of which is the amount of the contribution level for such Participant multiplied by such Participant’s Compensation (as defined in Section 9 below) during such Purchase Period and the denominator of which
is the lower of (i) eighty-five percent (85%) of the Fair Market Value of a share of the Common Stock on the Offering Date, or (ii) eighty-five percent (85%) of the Fair Market Value of a share of the Common Stock on the
Purchase Date; provided, however, that for the Purchase Period within the initial Offering Period the numerator shall be fifteen percent (15%) of the Participant’s Compensation for such Purchase Period, or such lower
percentage as determined by the Committee prior to the Effective Date or pursuant to a Participant’s election to lower the amount as set forth in Section 6(a) above, and provided, further, that the number of shares of Common
Stock subject to any option granted pursuant to this Plan shall not exceed the lesser of (x) the maximum number of shares set by the Committee pursuant to Section 10(b) below with respect to the applicable Purchase Date, or (y) the
maximum number of shares which may be purchased pursuant to Section 10(a) below with respect to the applicable Purchase Date. 
 8.
Purchase Price. The Purchase Price in any Offering Period shall be eighty-five percent (85%) of the lesser of: 

(a) The Fair Market Value on the Offering Date; or 

(b) The Fair Market Value on the Purchase Date. 

9. Payment of Purchase Price; Payroll Deduction Changes; Share Issuances.  

(a) The Purchase Price of the shares shall be accumulated by regular payroll deductions made during each Offering Period,
unless the Committee determines that contributions may be made in another form (including payment by check at the end of a Purchase Period). The deductions are made as a percentage of the Participant’s Compensation in one percent
(1%)

  
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increments not less than one percent (1%), nor greater than fifteen percent (15%) or such lower limit set by the Committee. “Compensation” shall mean all W-2 cash
compensation, including without limitation base salary or regular hourly wages, bonuses, incentive compensation, commissions, overtime, shift premiums, plus draws against commissions (or in foreign jurisdictions, equivalent cash compensation);
however, the Committee may at any time prior to the beginning of an Offering Period determine that for that and future Offering Periods, Compensation shall mean base salary or regular hourly wages (or in foreign jurisdictions, equivalent cash
compensation). For purposes of determining a Participant’s Compensation, any election by such Participant to reduce his or her regular cash remuneration under Sections 125 or 401(k) of the Code (or in foreign jurisdictions, equivalent salary
deductions) shall be treated as if the Participant did not make such election. Payroll deductions shall commence on the first payday following the last Purchase Date (or the first payday following the Effective Date of the Plan with respect to the
initial Offering Period) and shall continue to the end of the Offering Period unless sooner altered or terminated as provided in this Plan. Notwithstanding the foregoing, the terms of any subplan may permit matching shares without the payment of any
purchase price. 
 (b) Subject to Section 25 below and to the rules of the Committee, a Participant may make changes in
the rate of payroll deductions during an Offering Period or any Purchase Period by filing with the Company a new authorization for payroll deductions. 

(c) Subject to Section 25 below and to the rules of the Committee, a Participant may reduce his or her payroll deduction
percentage to zero during an Offering Period by filing with the Company a request for cessation of payroll deductions, and after such reduction becomes effective no further payroll deductions will be made for the duration of the Offering Period.
Payroll deductions credited to the Participant’s account prior to the effective date of the request shall be used to purchase shares of Common Stock in accordance with Section (e) below. A reduction of the payroll deduction percentage to
zero shall be treated as such Participant’s withdrawal from such Offering Period, and the Plan, effective as of the day after the next Purchase Date following the filing date of such request with the Company. 

(d) All payroll deductions made for a Participant are credited to his or her account under this Plan and are deposited with the
general funds of the Company, and the Company shall not be obligated to segregate such payroll deductions, except to the extent required to be segregated due to local legal restrictions outside the United States. No interest accrues on the payroll
deductions. All payroll deductions received or held by the Company may be used by the Company for any corporate purpose. 

(e) On each Purchase Date, so long as this Plan remains in effect and provided that the Participant has not submitted a signed
and completed withdrawal form before that date which notifies the Company and/or the Third Party Administrator that the Participant wishes to withdraw from that Offering Period under this Plan and have all payroll deductions accumulated in the
account maintained on behalf of the Participant as of that date returned to the Participant, the Company shall apply the funds then in the Participant’s account to the purchase of whole shares of Common Stock reserved under the option granted
to such Participant with respect to the Offering Period to the extent that such option is exercisable on the Purchase Date. The Purchase 

  
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Price shall be as specified in Section 8 of this Plan. Any fractional share, as calculated under this Subsection (e), shall be rounded down to the next lower whole share, unless the
Committee determines with respect to all Participants that any fractional share shall be credited as a fractional share. Any amount remaining in a Participant’s account on a Purchase Date which is less than the amount necessary to purchase a
full share of Common Stock shall be carried forward into the next Purchase Period or Offering Period, as the case may be (except to the extent required due to local legal requirements outside the United States), as otherwise determined by the
Committee. In the event that this Plan has been oversubscribed, all funds not used to purchase shares on the Purchase Date shall be returned to the Participant, without interest (except to the extent required due to local legal requirements outside
the United States). No Common Stock shall be purchased on a Purchase Date on behalf of any employee whose participation in this Plan has terminated prior to such Purchase Date. 

(f) As promptly as practicable after the Purchase Date, the Company shall issue shares for the Participant’s benefit
representing the shares purchased upon exercise of his or her option. 
 (g) During a Participant’s lifetime, his or her
option to purchase shares hereunder is exercisable only by him or her. The Participant will have no interest or voting right in shares covered by his or her option until such option has been exercised. 

(h) To the extent required by applicable federal, state, local or foreign law, a Participant shall make arrangements
satisfactory to the Company for the satisfaction of any withholding tax obligations that arise in connection with the Plan. The Company shall not be required to issue any shares of Common Stock under the Plan until such obligations are satisfied.

 10. Limitations on Shares to be Purchased. 

(a) No Participant shall be entitled to purchase stock under any Offering Period at a rate which, when aggregated with such
Participant’s rights to purchase stock, that are also outstanding in the same calendar year(s) (whether under other Offering Periods or other employee stock purchase plans of the Company, its Parent and its Subsidiaries), exceeds $25,000 in
Fair Market Value, determined as of the Offering Date, (or such other limit as may be imposed by the Code) for each calendar year in which such Offering Period is in effect (hereinafter the “Maximum Share Amount”). The Company may
automatically suspend the payroll deductions of any Participant as necessary to enforce such limit provided that when the Company automatically resumes such payroll deductions, the Company must apply the rate in effect immediately prior to such
suspension. 
 (b) The Committee may, in its sole discretion, set a lower maximum number of shares which may be purchased by
any Participant during any Offering Period than that determined under Section 10(a) above, which shall then be the Maximum Share Amount for subsequent Offering Periods; provided, however, in no event shall a Participant be permitted to purchase
more than two thousand (2,000) Shares during any one Purchase Period, irrespective of the Maximum Share Amount set forth in (a) and (b) hereof. If a new Maximum Share Amount is set, then all Participants will be notified of such
Maximum Share Amount prior to the commencement of the next Offering Period for which it is to be effective. The Maximum Share Amount shall continue to apply with respect to all succeeding Offering Periods unless revised by the Committee as set forth
above. 

  
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 (c) If the number of shares to be purchased on a Purchase Date by all
Participants exceeds the number of shares then available for issuance under this Plan, then the Company will make a pro rata allocation of the remaining shares in as uniform a manner as shall be reasonably practicable and as the Committee shall
determine to be equitable. In such event, the Company will give written notice of such reduction of the number of shares to be purchased under a Participant’s option to each Participant affected. 

(d) Any payroll deductions accumulated in a Participant’s account which are not used to purchase stock due to the
limitations in this Section 10, and not covered by Section 9(e), shall be returned to the Participant as soon as administratively practicable after the end of the applicable Purchase Period, without interest (except to the extent required
due to local legal requirements outside the United States). 
 11. Withdrawal. 

(a) Each Participant may withdraw from an Offering Period under this Plan pursuant to a method specified by the Company. Such
withdrawal may be elected at any time prior to the end of an Offering Period, or such other time period as specified by the Committee. 

(b) Upon withdrawal from this Plan, the accumulated payroll deductions shall be returned to the withdrawn Participant, without
interest, and his or her interest in this Plan shall terminate. In the event a Participant voluntarily elects to withdraw from this Plan, he or she may not resume his or her participation in this Plan during the same Offering Period, but he or she
may participate in any Offering Period under this Plan which commences on a date subsequent to such withdrawal by filing a new authorization for payroll deductions in the same manner as set forth in Section 6 above for initial participation in
this Plan. 
 12. Termination of Employment. Termination of a Participant’s employment for any reason, including retirement,
death, disability, or the failure of a Participant to remain an eligible employee of the Company or of a Participating Corporation, immediately terminates his or her participation in this Plan. In such event, accumulated payroll deductions credited
to the Participant’s account will be returned to him or her or, in the case of his or her death, to his or her legal representative, without interest (except to the extent required due to local legal requirements outside the United States). For
purposes of this Section 12, an employee will not be deemed to have terminated employment or failed to remain in the continuous employ of the Company or of a Participating Corporation in the case of sick leave, military leave, or any other
leave of absence approved by the Company; provided that such leave is for a period of not more than ninety (90) days or reemployment upon the expiration of such leave is guaranteed by contract or statute. The Company will have sole
discretion to determine whether a Participant has terminated employment and the effective date on which the Participant terminated employment, regardless of any notice period or garden leave required under local law. 

  
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 13. Return of Payroll Deductions. In the event a Participant’s interest in this Plan
is terminated by withdrawal, termination of employment or otherwise, or in the event this Plan is terminated by the Board, the Company shall deliver to the Participant all accumulated payroll deductions credited to such Participant’s account.
No interest shall accrue on the payroll deductions of a Participant in this Plan (except to the extent required due to local legal requirements outside the United States). 

14. Capital Changes. If the number of outstanding Shares is changed by a stock dividend, recapitalization, stock split, reverse stock
split, subdivision, combination, reclassification or similar change in the capital structure of the Company, without consideration, then the Committee shall adjust the number and class of Common Stock that may be delivered under the Plan, the
Purchase Price and the number of shares of Common Stock covered by each option under the Plan which has not yet been exercised, and the numerical limits of Sections 1 and 10 shall be proportionately adjusted, subject to any required action by the
Board or the stockholders of the Company and in compliance with applicable securities laws; provided that fractions of a Share will not be issued. 

15. Nonassignability. Neither payroll deductions credited to a Participant’s account nor any rights with regard to the exercise of
an option or to receive shares under this Plan may be assigned, transferred, pledged or otherwise disposed of in any way (other than by will, the laws of descent and distribution or as provided in Section 22 below) by the Participant. Any such
attempt at assignment, transfer, pledge or other disposition shall be void and without effect. 
 16. Use of Participant Funds and
Reports. The Company may use all payroll deductions received or held by it under the Plan for any corporate purpose, and the Company will not be required to segregate Participant payroll deductions (except to the extent required due to local
legal requirements outside the United States). Until Shares are issued, Participants will only have the rights of an unsecured creditor. Each Participant shall receive, or have access to, promptly after the end of each Purchase Period a report of
his or her account setting forth the total payroll deductions accumulated, the number of shares purchased, the Purchase Price thereof and the remaining cash balance, if any, carried forward or refunded, as determined by the Committee in conformance
with Section 9 of the Plan, to the next Purchase Period or Offering Period, as the case may be. 
 17. Notice of Disposition.
Each U.S. taxpayer Participant shall notify the Company in writing if the Participant disposes of any of the shares purchased in any Offering Period pursuant to this Plan if such disposition occurs within two (2) years from the Offering Date or
within one (1) year from the Purchase Date on which such shares were purchased (the “Notice Period”). The Company may, at any time during the Notice Period, place a legend or legends on any certificate representing
shares acquired pursuant to this Plan requesting the Company’s transfer agent to notify the Company of any transfer of the shares. The obligation of the Participant to provide such notice shall continue notwithstanding the placement of any such
legend on the certificates. 
 18. No Rights to Continued Employment. Neither this Plan nor the grant of any option hereunder shall
confer any right on any employee to remain in the employ of the Company or any Participating Corporation, or restrict the right of the Company or any Participating Corporation to terminate such employee’s employment. 

  
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 19. Equal Rights And Privileges. All eligible employees granted an option under this Plan
that is intended to meet the Code Section 423 requirements shall have equal rights and privileges with respect to this Plan or within any separate offering under the Plan so that this Plan qualifies as an “employee stock purchase
plan” within the meaning of Section 423 or any successor provision of the Code and the related regulations. Any provision of this Plan which is inconsistent with Section 423 or any successor provision of the Code shall, without
further act or amendment by the Company or the Committee, be reformed to comply with the requirements of Section 423. This Section 19 shall take precedence over all other provisions in this Plan. 

20. Notices. All notices or other communications by a Participant to the Company under or in connection with this Plan shall be deemed
to have been duly given when received in the form specified by the Company at the location, or by the person, designated by the Company for the receipt thereof. 

21. Term; Stockholder Approval. This Plan will become effective on the Effective Date. This Plan shall be approved by the stockholders
of the Company, in any manner permitted by applicable corporate law, within twelve (12) months before or after the date this Plan is adopted by the Board. No purchase of shares that are subject to such stockholder approval before becoming
available under this Plan shall occur prior to stockholder approval of such shares and the Committee may delay any Purchase Date and postpone the commencement of any Offering Period subsequent to such Purchase Date as deemed necessary or desirable
to obtain such approval (provided that if a Purchase Date would occur more than twenty-four (24) months after commencement of the Offering Period to which it relates, then such Purchase Date shall not occur and instead such Offering Period
shall terminate without the purchase of such shares and Participants in such Offering Period shall be refunded their contributions without interest). This Plan shall continue until the earlier to occur of (a) termination of this Plan by the
Board (which termination may be effected by the Board at any time pursuant to Section 25 below), (b) issuance of all of the shares of Common Stock reserved for issuance under this Plan, or (c) the tenth anniversary of the first
Purchase Date under the Plan. 
 22. Designation of Beneficiary. 

(a) If provided in the subscription agreement, a Participant may file a written or electronic designation of a beneficiary who
is to receive any shares and cash, if any, from the Participant’s account under this Plan in the event of such Participant’s death subsequent to the end of a Purchase Period but prior to delivery to him of such shares and cash. In
addition, a Participant may file a written or electronic designation of a beneficiary who is to receive any cash from the Participant’s account under this Plan in the event of such Participant’s death prior to a Purchase Date. Such form
shall be valid only if it was filed with the Company and/or the Third Party Administrator at the prescribed location before the Participant’s death. 

  
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 (b) Such designation of beneficiary may be changed by the Participant at any time
by written notice filed with the Company at the prescribed location before the Participant’s death. In the event of the death of a Participant and in the absence of a beneficiary validly designated under this Plan who is living at the time of
such Participant’s death, the Company shall deliver such cash to the executor or administrator of the estate of the Participant, or if no such executor or administrator has been appointed (to the knowledge of the Company), the Company, in its
discretion, may deliver such shares or cash to the spouse or, if no spouse is known to the Company, then to any one or more dependents or relatives of the Participant, or if no spouse, dependent or relative is known to the Company, then to such
other person as the Company may designate. 
 23. Conditions Upon Issuance of Shares; Limitation on Sale of Shares. Shares shall not
be issued with respect to an option unless the exercise of such option and the issuance and delivery of such shares pursuant thereto shall comply with all applicable provisions of law, domestic or foreign, including, without limitation, the
Securities Act, the Exchange Act, the rules and regulations promulgated thereunder, and the requirements of any stock exchange or automated quotation system upon which the shares may then be listed, exchange control restrictions and/or securities
law restrictions outside the United States, and shall be further subject to the approval of counsel for the Company with respect to such compliance. Shares may be held in trust or subject to further restrictions as permitted by any subplan. 

24. Applicable Law. The Plan shall be governed by the substantive laws (excluding the conflict of laws rules) of the State of Delaware.

 25. Amendment or Termination. The Committee, in its sole discretion, may amend, suspend, or terminate the Plan, or any part
thereof, at any time and for any reason. If the Plan is terminated, the Committee, in its discretion, may elect to terminate all outstanding Offering Periods either immediately or upon completion of the purchase of shares of Common Stock on the next
Purchase Date (which may be sooner than originally scheduled, if determined by the Committee in its discretion), or may elect to permit Offering Periods to expire in accordance with their terms (and subject to any adjustment pursuant to
Section 14). If an Offering Period is terminated prior to its previously-scheduled expiration, all amounts then credited to Participants’ accounts for such Offering Period, which have not been used to purchase shares of Common Stock, shall
be returned to those Participants (without interest thereon, except as otherwise required under local laws) as soon as administratively practicable. Further, the Committee will be entitled to establish rules to change the Purchase Periods and
Offering Periods, limit the frequency and/or number of changes in the amount withheld during a Purchase Period or an Offering Period, establish the exchange ratio applicable to amounts withheld in a currency other than U.S. dollars, permit payroll
withholding in excess of the amount designated by a Participant in order to adjust for delays or mistakes in the administration of the Plan, establish reasonable waiting and adjustment periods and/or accounting and crediting procedures to ensure
that amounts applied toward the purchase of Common Stock for each Participant properly correspond with amounts withheld from the Participant’s base salary or regular hourly wages, and establish such other limitations or procedures as the
Committee determines in its sole discretion advisable which are consistent with the Plan. Such actions will not require stockholder approval or the consent of any Participants. However, no amendment shall be made without approval of the stockholders
of the Company (obtained in accordance with Section 21 above) within twelve (12) months of the adoption of such amendment (or earlier if 

  
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required by Section 21) if such amendment would: (a) increase the number of shares that may be issued under this Plan; or (b) change the designation of the employees (or class of
employees) eligible for participation in this Plan. In addition, in the event the Committee determines that the ongoing operation of the Plan may result in unfavorable financial accounting consequences, the Committee may, in its discretion and, to
the extent necessary or desirable, modify, amend or terminate the Plan to reduce or eliminate such accounting consequences including, but not limited to: (i) amending the definition of Compensation, including with respect to an Offering Period
underway at the time; (ii) altering the Purchase Price for any Offering Period including an Offering Period underway at the time of the change in Purchase Price; (iii) shortening any Offering Period by setting a Purchase Date, including an
Offering Period underway at the time of the Committee action; (iv) reducing the maximum percentage of compensation a participant may elect to set aside as payroll deductions; and (v) reducing the maximum number of shares of Common Stock a
Participant may purchase during any Offering Period. Such modifications or amendments will not require approval of the stockholders of the Company or the consent of any Participants. 

26. Corporate Transactions. In the event of a Corporate Transaction (as defined below), each outstanding right to purchase Common Stock
will be assumed or an equivalent option substituted by the successor corporation or a parent or a subsidiary of the successor corporation. In the event that the successor corporation refuses to assume or substitute for the purchase right, the
Offering Period with respect to which such purchase right relates will be shortened by setting a new Purchase Date (the “New Purchase Date”) and will end on the New Purchase Date. The New Purchase Date shall occur on or prior
to the consummation of the Corporate Transaction, and the Plan shall terminate on the consummation of the Corporate Transaction. 
 27.
Definitions. 
 (a) “Affiliate” means (i) any entity that, directly or indirectly, is
controlled by, controls or is under common control with, the Company and (ii) any entity in which the Company has a significant equity interest, in either case as determined by the Committee, whether now or hereafter existing. 

(b) “Board” shall mean the Board of Directors of the Company. 

(c) “Code” shall mean the Internal Revenue Code of 1986, as amended. 

(d) “Common Stock” shall mean the Class B common stock of the Company. 

(e) “Company” shall mean Castlight Health, Inc., a Delaware corporation. 

(f) “Corporate Transaction” means the occurrence of any of the following events: (i) any
“person” (as such term is used in Sections 13(d) and 14(d) of the Exchange Act) becomes the “beneficial owner” (as defined in Rule 13d-3 of the Exchange Act), directly or indirectly, of securities of the Company representing
fifty percent (50%) or more of the total voting power represented by the Company’s then outstanding voting securities; or (ii) the 

  
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consummation of the sale or disposition by the Company of all or substantially all of the Company’s assets; or (iii) the consummation of a merger or consolidation of the Company with
any other corporation, other than a merger or consolidation which would result in the voting securities of the Company outstanding immediately prior thereto continuing to represent (either by remaining outstanding or by being converted into voting
securities of the surviving entity or its parent) at least fifty percent (50%) of the total voting power represented by the voting securities of the Company or such surviving entity or its parent outstanding immediately after such merger or
consolidation. 
 (g) “Effective Date” shall mean the date on which the Registration Statement
covering the initial public offering of the shares of Common Stock is declared effective by the U.S. Securities and Exchange Commission. 

(h) “Exchange Act” shall mean the Securities Exchange Act of 1934, as amended. 

(i) “Fair Market Value” shall mean, as of any date, the value of a share of Common Stock determined as
follows: 
 (i) if such Common Stock is publicly traded and is then listed on a national securities exchange, its closing
price on the date of determination on the principal national securities exchange on which the Common Stock is listed or admitted to trading as reported in The Wall Street Journal or such other source as the Committee deems reliable; or 

(ii) if such Common Stock is publicly traded but is neither listed nor admitted to trading on a national securities exchange,
the average of the closing bid and asked prices on the date of determination as reported in The Wall Street Journal or such other source as the Committee deems reliable; or 

(iii) if such Common Stock is publicly traded but is neither quoted on the Nasdaq Market nor listed or admitted to trading on a
national securities exchange, the average of the closing bid and asked prices on the date of determination as reported in The Wall Street Journal or such other source as the Committee deems reliable; or 

(iv) with respect to the initial Offering Period, Fair Market Value on the Offering Date shall be the price at which shares of
Common Stock are offered to the public by the Company’s underwriters pursuant to the Registration Statement covering the initial public offering of shares of Common Stock; and 

(v) if none of the foregoing is applicable, by the Committee in good faith. 

(j) “Offering Date” shall mean the first business day of each Offering Period. However, for the initial
Offering Period the Offering Date shall be the Effective Date. 

  
 12 








 (k) “Offering Period” shall mean a period with respect to
which the right to purchase Common Stock may be granted under the Plan, as determined by the Committee pursuant to Section 5(a). 

(l) “Parent” shall have the same meaning as “parent corporation” in Sections 424(e) and
424(f) of the Code. 
 (m) “Participant” shall mean an eligible employee who meets the eligibility
requirements set forth in Section 4 and who is either automatically enrolled in the initial Offering Period or who elects to participate in this Plan pursuant to Section 6(b). 

(n) “Participating Corporation” shall mean any Parent, Subsidiary or Affiliate that the Board
designates from time to time as a corporation that shall participate in this Plan. 
 (o) “Plan”
shall mean this Castlight Health, Inc. 2014 Employee Stock Purchase Plan. 
 (p) “Purchase Date”
shall mean the last U.S. business day of each Purchase Period. 
 (q) “Purchase Period” shall mean a
period during which contributions may be made toward the purchase of Common Stock under the Plan, as determined by the Committee pursuant to Section 5(b). 

(r) “Purchase Price” shall mean the price at which Participants may purchase a share of Common Stock
under the Plan, as determined pursuant to Section 8. 
 (s) “Subsidiary” shall have the same
meaning as “subsidiary corporation” in Sections 424(e) and 424(f) of the Code. 

  
 13 









					
	Castlight Health, Inc. (the “Company”)	  	U.S. Enrollment/Change Form
	
	 2014 EMPLOYEE STOCK PURCHASE PLAN (“ESPP”)

(Capitalized terms not defined in this form shall have the meaning set forth in the ESPP.)



 

							
	 SECTION 1:
 ACTIONS
	  	 CHECK DESIRED ACTION: 

 

 ̈       Enroll in the ESPP

 ̈       Change Contribution
Percentage
  ̈       Discontinue
Contributions (withdrawal)
	  	 AND COMPLETE SECTIONS:

 
 2 + 3 + 4 + 7

2 + 4 + 7
 2 + 5 + 7
	  	
			
	 SECTION 2:
 PERSONAL DATA
	  	 Name:
                                         
                                         
                          

Home Address:
                                         
                                         
            
 ____________________________________________________________

 
 Social Security / Identification No.:
                                         
                     
	  	  
  

Department:
 _____________

		
	 SECTION 3:
 ENROLL
	  	 I hereby elect to participate in the ESPP, effective at the beginning of the next Offering Period. I elect to purchase shares of
the Common Stock of the Company subject to the terms and conditions of the ESPP and this Enrollment/Change Form (the “Enrollment/Change Form”). I understand that shares of Common Stock purchased on my behalf will be issued in street name
and deposited directly into my brokerage account with [Broker] or its affiliates. I hereby agree to take all steps, and sign all forms, required to establish an account with [Broker] or its affiliates for this purpose.

 
 My participation will continue as long as I remain eligible, unless I withdraw from the
ESPP by filing a new Enrollment/Change Form with the Company. I understand that I must notify the Company of any disposition of shares of Common Stock purchased under the ESPP.

		
	 SECTION 4:
 ELECT CONTRIBUTION
PERCENTAGE
	  	 I hereby authorize the Company to withhold from each of my paychecks __% of my Compensation (as defined in the ESPP) paid during
such Offering Period as long as I continue to participate in the ESPP or otherwise instruct the Company by filing a subsequent Enrollment/Change Form. That amount will be applied to the purchase of shares of the Company’s Common Stock pursuant
to the ESPP. The percentage must be a whole number (from 1%, up to a maximum of 15%).
  

If this is a change to my current enrollment, this represents an  ̈-increase
 ̈-decrease to my contribution percentage.
  

Note: You may not increase your contribution at any time within a Purchase Period. You may decrease your contribution percentage to a percentage other
than 0% only once within a Purchase Period to be effective during that Purchase Period. A change will become effective as soon as reasonably practicable after the form is received by the Company. An increase in your contribution percentage can
only take effect with the next Offering Period.










			
	 SECTION 5:
 DISCONTINUE
CONTRIBUTIONS
	  	  ̈       I hereby
elect to stop my contributions under the ESPP, effective as soon as reasonably practicable after this form is received by the Company.
  

Please  ̈-refund all contributions to me in cash, without interest OR  ̈- use my contributions to purchase shares on the next Purchase Date. I understand that I cannot resume participation until the start of the next Offering Period and must timely file a new enrollment form
to do so.

		
	 SECTION 6:
 ELECTRONIC DELIVERY AND
ACCEPTANCE
	  	The Company may, in its sole discretion, decide to deliver any documents related to current or future participation in the ESPP by electronic means. I hereby consent to receive such documents by electronic delivery and agree to
participate in the ESPP through an on-line or electronic system established and maintained by the Company or a third party designated by the Company.
		
	 SECTION 7:
 ACKNOWLEDGMENT AND
SIGNATURE
	  	 I understand that this Enrollment/Change Form will remain in effect throughout successive offering periods unless terminated by me or I
become ineligible to participate in the ESPP.
  
 I acknowledge that I have received a
copy of the ESPP and of the Prospectus (which summarizes the major features of the ESPP). I have read the ESPP and the Prospectus and my signature below (or my clicking on the Accept box if this is an electronic form) indicates that I hereby agree
to be bound by the terms of the ESPP and this Enrollment/Change Form.
 Signature:
                                         
                                         
                               Date: