SEC FORM 3

SEC Form 3

FORM 3

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

INITIAL STATEMENT OF BENEFICIAL OWNERSHIP OF SECURITIES

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person^*

Nolan Mangini Siobhan

(Last)

(First)

(Middle)

C/O CASTLIGHT HEALTH, INC.

150 SPEAR ST., SUITE 400

(Street)

SAN FRANCISCO

94105

(City)

(State)

(Zip)

2. Date of Event Requiring Statement (Month/Day/Year)
07/08/2016

3. Issuer Name and Ticker or Trading Symbol
CASTLIGHT HEALTH, INC. [ CSLT ]

4. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director	10% Owner
X	Officer (give title below)	Other (specify below)
	CFO & Treasurer

5. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Beneficially Owned
1. Title of Security (Instr. 4)	2. Amount of Securities Beneficially Owned (Instr. 4)	3. Ownership Form: Direct (D) or Indirect (I) (Instr. 5)	4. Nature of Indirect Beneficial Ownership (Instr. 5)
Class B common stock	12,713	D

Table II - Derivative Securities Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 4)	2. Date Exercisable and Expiration Date (Month/Day/Year)		3. Title and Amount of Securities Underlying Derivative Security (Instr. 4)		4. Conversion or Exercise Price of Derivative Security	5. Ownership Form: Direct (D) or Indirect (I) (Instr. 5)	6. Nature of Indirect Beneficial Ownership (Instr. 5)
1. Title of Derivative Security (Instr. 4)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	4. Conversion or Exercise Price of Derivative Security	5. Ownership Form: Direct (D) or Indirect (I) (Instr. 5)	6. Nature of Indirect Beneficial Ownership (Instr. 5)
Employee Stock Option (right to buy)	⁽¹⁾	06/07/2022	Class A common stock⁽²⁾⁽³⁾	10,500	$1.08	D
Employee Stock Option (right to buy)	⁽⁴⁾	07/23/2023	Class A common stock⁽²⁾⁽³⁾	17,500	$1.29	D
Employee Stock Option (right to buy)	⁽⁵⁾	10/24/2023	Class A common stock⁽²⁾⁽³⁾	20,167	$2.35	D
Employee Stock Option (right to buy)	⁽⁶⁾	02/23/2026	Class A common stock⁽²⁾⁽³⁾	10,000	$2.99	D
Restricted Stock Units	⁽⁷⁾	⁽⁷⁾	Class B common stock	5,782	$0⁽⁸⁾	D
Restricted Stock Units	⁽⁹⁾	⁽⁹⁾	Class B common stock	6,875	$0⁽⁸⁾	D
Restricted Stock Units	⁽¹⁰⁾	⁽¹⁰⁾	Class B common stock	30,000	$0⁽⁸⁾	D
Restricted Stock Units	⁽¹¹⁾	⁽¹¹⁾	Class B common stock	40,000	$0⁽⁸⁾	D
Restricted Stock Units	⁽¹²⁾	⁽¹²⁾	Class B common stock	30,000	$0⁽⁸⁾	D

Explanation of Responses:

1. 20% of the shares subject to the option vested on February 27, 2013. Thereafter, the shares vested or will vest in twelve installments each consisting of 1.667% of the shares subject to the option after the completion of each additional consecutive month of service, then with respect to the remaining shares, in 24 equal installments upon the completion of each additional consecutive month of service thereafter.

2. Each share of Class A Common Stock is convertible, at any time at the option of the holder, into one (1) share of Class B Common Stock. In addition, each share of Class A Common Stock will convert automatically into one (1) share of Class B Common Stock upon the transfer, whether or not for value, that occurs after the closing of the IPO to any transferee who is not a "Permitted Transferee", as defined in the Issuer's Restated Certificate of Incorporation in effect as of the date hereof. The shares of Class A Common Stock have no expiration date.

3. Each share of the Issuer's Class A Common Stock will convert automatically into one (1) share of Class B Common Stock upon the earliest to occur of the following: (a) the first date on which the number of shares of Class A Common Stock then outstanding is less than 15,340,384 shares, (b) March 19, 2024, or (c) a time and date approved in writing by holders of at least a majority of the then-outstanding shares of Class A Common Stock. The shares of Class A Common Stock and Class B Common Stock have no expiration date.

4. 20% of the shares subject to the option vested on June 1, 2014. Thereafter, the shares vested or will vest in twelve installments each consisting of 1.667% of the shares subject to the option after the completion of each additional consecutive month of service, then with respect to the remaining shares, in 24 equal installments upon the completion of each additional consecutive month of service thereafter.

5. The stock option vested or will vest in 48 equal monthly installments beginning on October 23, 2014, until such time as the option is 100% vested, subject to the continuing employment of the Reporting Person on each vesting date.

6. The stock option vested or will vest in 60 equal monthly installments beginning on March 24, 2016, until such time as the option is 100% vested, subject to the continuing employment of the Reporting Person on each vesting date.

7. 25% of the restricted stock units ("RSUs") vested on November 17, 2015 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.

8. Each RSU represents a contingent right to receive 1 share of the Issuer's Class B common stock upon settlement for no consideration.

9. 25% of the RSUs vested on February 15, 2016 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.

10. 25% of the RSUs will vest on August 15, 2016 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.

11. 25% of the RSUs will vest on November 16, 2016 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.

12. 25% of the RSUs will vest on February 16, 2017 and the remainder will vest quarterly over three years thereafter in equal installments. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be sold by the Reporting Person to cover any tax withholding obligations.

	/s/ Jennifer Chaloemtiarana, by power of attorney	07/12/2016
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 5 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
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