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
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.
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.
Insider Trade Summary
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Stock Option (Right to Buy) | 555,165 | $0.00 | -- |
| Exercise | Class B Common Stock | 555,165 | $6.36 | $3.53M |
| Conversion | Class B Common Stock | 395,000 | $0.00 | -- |
| Conversion | Class A Common Stock | 395,000 | $0.00 | -- |
| Sale | Class A Common Stock | 395,000 | $18.43 | $7.28M |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
| holding | Class B Common Stock | -- | -- | -- |
Footnotes (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. 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. 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. The stock option is fully vested and exercisable, and expires on December 7, 2025. 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.
