OSCR Form 4: CTO exercised 555,165 options and executed sell-to-cover of 395,000 shares

Rhea-AI Filing Summary

Oscar Health insider filings show option exercise and share sale by Mario Schlosser. Mr. Schlosser exercised 555,165 vested stock options with a $6.36 exercise price on 09/22/2025, creating the right to 555,165 Class A shares. Concurrently he converted and sold 395,000 Class A shares in multiple transactions at a weighted average price of $18.43 to cover the exercise cost and tax withholding, leaving him with 501,148 Class A shares beneficially owned. Certain remaining shares are held indirectly in family dynasty trusts over which he disclaims beneficial ownership except for any pecuniary interest.

Positive

• Large vested option exercised (555,165 options), indicating prior compensation vesting and potential management retention alignment
• Comprehensive disclosure including sale price range, purpose (cover exercise and tax withholding), option expiry date, and trust holdings

Negative

• Sale of 395,000 shares reduced directly held Class A shares, which may modestly increase available float
• Substantial number of options and shares remain exercisable or convertible, representing potential future dilution

Insights

Securities Analyst

TL;DR: Director exercised a large, fully vested option package and sold shares to satisfy exercise and tax obligations; ownership remains significant.

The filing documents a routine but sizable option exercise and related sell-to-cover transactions. Exercise price of $6.36 versus sale-weighted price $18.43 implies a realized spread per sold share, with 395,000 shares sold to fund costs and withholding. Post-transaction direct beneficial ownership of Class A shares is 501,148, and combined direct plus convertible Class B rights total materially higher, indicating continued alignment with company equity despite liquidity events.

Corporate Governance Expert

TL;DR: Disclosure is complete and standard: vested options exercised, multiple trust holdings noted, and sale explained as tax/expense coverage.

The Form 4 discloses conversion mechanics of Class B to Class A shares, expiration date of the option (12/07/2025), and trust holdings with disclaimer of beneficial ownership except for pecuniary interest. The reporting and explanatory footnotes conform to Section 16 transparency expectations and identify that the sale was effected in multiple transactions at prices between $18.25 and $18.78.

SEC Form 4

FORM 4

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

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

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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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

Schlosser Mario

(Last) (First) (Middle)

75 VARICK STREET, 5TH FLOOR

(Street)

NEW YORK NY 10013

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Oscar Health, Inc. [ OSCR ]

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

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	President of Technology & CTO

3. Date of Earliest Transaction (Month/Day/Year)
09/22/2025

4. 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 Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Class A Common Stock	09/22/2025		C		395,000	A	(1)	896,148	D
Class A Common Stock	09/22/2025		S(2)		395,000	D	$18.43(3)	501,148	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Stock Option (Right to Buy)	$6.36	09/22/2025		M			555,165	(4)	12/07/2025	Class B Common Stock	555,165	$0.00	555,165	D
Class B Common Stock	(1)	09/22/2025		M		555,165		(1)	(1)	Class A Common Stock	555,165	$6.36	1,910,303	D
Class B Common Stock	(1)	09/22/2025		C			395,000	(1)	(1)	Class A Common Stock	395,000	$0.00(1)	1,515,303	D
Class B Common Stock	(1)							(1)	(1)	Class A Common Stock	333,333		333,333	I	By Noah Pizzo-Schlosser Dynasty Trust(5)
Class B Common Stock	(1)							(1)	(1)	Class A Common Stock	633,333		633,333	I	By Pizzo-Schlosser Family Dynasty Trust(5)
Class B Common Stock	(1)							(1)	(1)	Class A Common Stock	333,333		333,333	I	By Siena Pizzo-Schlosser Dynasty Trust(5)

Explanation of Responses:

1. The Class B common stock is convertible at any time at the option of the holder into Class A common stock on a one-to-one basis, subject to certain exceptions, and will mandatorily convert into Class A common stock on the date that is seven years from the date of the prospectus used in connection with the Issuer's initial public offering and upon the occurrence of certain events as set forth in the Issuer's certificate of incorporation.

2. The sale was effected to cover the cost of exercise and to satisfy the Reporting Person's tax withholding obligation arising from the stock option exercise reported herein.

3. The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $18.25 to $18.78, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price at which the transactions were effected.

4. The stock option is fully vested and exercisable, and expires on December 7, 2025.

5. Mr. Schlosser disclaims beneficial ownership over the shares held of record by the trust except to the extent of his pecuniary interest therein, if any.

Remarks:

	/s/ Melissa Curtin, Attorney-in-fact	09/24/2025
	** 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 4 (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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FAQ

What did Mario Schlosser report on the Form 4 for OSCR?

He exercised 555,165 stock options on 09/22/2025 and sold 395,000 Class A shares at a weighted average price of $18.43 to cover exercise costs and tax withholding.

How many shares does Mario Schlosser own after the transactions (OSCR)?

He beneficially owns 501,148 Class A shares directly following the reported transactions, plus additional convertible/derivative interests reflected in the filing.

What was the exercise price and expiry for the options exercised?

The options had a $6.36 exercise price and the underlying stock option expires on 12/07/2025.

Why were shares sold in the transaction disclosed on Form 4?

The sale of 395,000 shares was effected to cover the cost of exercise and to satisfy the reporting person’s tax withholding obligation arising from the option exercise.

Were any shares held indirectly in trusts disclosed?

Yes. Shares are held of record by family dynasty trusts and Mr. Schlosser disclaims beneficial ownership except to the extent of any pecuniary interest.