Neeraj Gupta Form 3 CASTLIGHT HEALTH / Neeraj Gupta ownership change

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^*

Gupta Neeraj

(Last) (First) (Middle)

C/O CASTLIGHT HEALTH, INC.

150 SPEAR ST., SUITE 400

(Street)

SAN FRANCISCO CA 94105

(City) (State) (Zip)

2. Date of Event Requiring Statement (Month/Day/Year)
09/17/2018

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)
EVP, Engineering

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	228,169	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)
	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Restricted Stock Units	(1)	(1)	Class B Common Stock	200,000	0(2)	D
Restricted Stock Units	(3)	(3)	Class B Common Stock	31,250	0(2)	D
Restricted Stock Units	(4)	(4)	Class B Common Stock	113,750	0(2)	D
Restricted Stock Units	(5)	(5)	Class B Common Stock	50,000	0(2)	D

Explanation of Responses:

1. 25% of the restricted stock units ("RSUs") vested on August 16, 2017 and the remainder vested and will continue to 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 automatically sold on behalf of the Reporting Person to cover any tax withholding obligations.

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

3. 25% of the RSUs vested on March 7, 2018 and the remainder vested and will continue to vest quarterly over three years thereafter in equal installments, beginning on May 16, 2018. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be automatically sold on behalf of the Reporting Person to cover any tax withholding obligations

4. The RSUs vested, and will continue to vest, in equal quarterly installments over four years, beginning on May 16, 2018. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be automatically sold on behalf of the Reporting Person to cover any tax withholding obligations.

5. 33.3% of the RSUs will vest on December 31, 2018, 33.3% of the RSUs will vest on December 31, 2019 and the remaining 33.3% of the RSUs will vest on December 31, 2020. Shares of the Issuer's Class B common stock will be delivered to the Reporting Person following vesting, at which time shares will be automatically sold on behalf of the Reporting Person to cover any tax withholding obligations.

	/s/ Jennifer Chaloemtiarana, by power of attorney	09/19/2018
	** 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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