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^*

Bondurant William

(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)
11/15/2019

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)
	Chief Financial Officer

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	63,996	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⁾	07/23/2023	Class A Common Stock⁽²⁾	1,750	$1.29	D
Employee Stock Option (right to buy)	⁽¹⁾	10/24/2023	Class A Common Stock⁽²⁾	5,757	$2.35	D
Employee Stock Option (right to buy)	⁽³⁾	02/23/2026	Class B Common Stock	7,500	$2.99	D
Employee Stock Option (right to buy)	⁽⁴⁾	02/23/2026	Class B Common Stock	12,000	$2.99	D
Employee Stock Option (right to buy)	⁽³⁾	02/23/2026	Class B Common Stock	6,000	$2.99	D
Employee Stock Option (right to buy)	⁽⁵⁾	02/13/2029	Class B Common Stock	10,000	$3.22	D
Restricted Stock Units (RSU)	⁽⁶⁾	⁽⁶⁾	Class B Common Stock	4,375	⁽⁷⁾	D
Restricted Stock Units (RSU)	⁽⁸⁾	⁽⁸⁾	Class B Common Stock	10,000	⁽⁷⁾	D
Restricted Stock Units (RSU)	⁽⁹⁾	⁽⁹⁾	Class B Common Stock	37,500	⁽⁷⁾	D
Restricted Stock Units (RSU)	⁽⁹⁾	⁽⁹⁾	Class B Common Stock	15,000	⁽⁷⁾	D
Restricted Stock Units (RSU)	⁽¹⁰⁾	⁽¹⁰⁾	Class B Common Stock	39,375	⁽⁷⁾	D

Explanation of Responses:

1. The stock option has fully vested and is immediately exercisable.

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 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, (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, and (d) the transfer, whether or not for value, 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. The stock option vested and continues to vest in 60 equal monthly installments beginning on February 24, 2016, until such time as the option is 100% vested, subject to the continuing service of the Reporting Person on each vesting date.

4. The stock option vested and continues to vest in 48 equal monthly installments beginning on February 24, 2016, until such time as the option is 100% vested, subject to the continuing service of the Reporting Person on each vesting date.

5. The stock option vested and continues to vest in 12 equal quarterly installments over three years, with the first vesting date being May 16, 2019, until such time as the option is 100% vested, subject to the continuing service of the Reporting Person on each vesting date.

6. 1/4th of the RSUs vested on May 16, 2018, and the remainder will vest 1/16th quarterly over three years in equal installments, subject to the continuing service of the Reporting Person on each vesting date.

7. Each RSU represents a contingent right to receive one (1) share of the Class B Common Stock upon settlement for no consideration.

8. 1/4th of the RSUs vested on August 16, 2018, and the remainder will vest 1/16th quarterly over three years in equal installments, subject to the continuing service of the Reporting Person on each vesting date.

9. 1/16th of the RSUs vested on November 16, 2018, and the remainder will vest 1/16th quarterly thereafter in equal installments, subject to the continuing service of the Reporting Person on each vesting date.

10. 1/16th of the RSUs vested on May 16, 2019, and the remainder will vest 1/16th quarterly thereafter in equal installments, subject to the continuing service of the Reporting Person on each vesting date.

	/s/ William Bondurant, by Trevor Dutcher, Attorney-in-Fact	11/18/2019
	** 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).
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