Form 4: Oscar Health CFO Sells Shares Under 10b5-1 Plan

Oscar Health's Chief Financial Officer, Richard Scott Blackley, has sold a significant number of Class A Common Stock shares as part of a pre-arranged trading plan.

Summary

• Richard Scott Blackley, Chief Financial Officer of Oscar Health, Inc., reported transactions involving the sale of Class A Common Stock on June 2, 2026.
• A total of 22,706 shares were sold at a weighted average price of $21.74, with individual sales ranging from $21.03 to $22.02.
• An additional 8,977 shares were sold at a weighted average price of $22.45, with individual sales ranging from $22.03 to $22.96.
• These sales were executed under a Rule 10b5-1 trading plan established on August 8, 2025, intended to satisfy the reporting person's tax withholding obligations upon the vesting of equity awards.
• Following these transactions, Blackley beneficially owns 1,083,954 shares directly and 1,074,977 shares indirectly, with 75,000 shares held by the MQB Irrevocable Trust.

Sentiment

Score: 5

Explanation: StockSavvy.ai views this as a neutral filing. While a significant number of shares were sold by a key executive, the transactions were conducted under a pre-arranged Rule 10b5-1 plan to cover tax obligations, which is a standard and often necessary procedure.

Positives

• The sales were conducted under a Rule 10b5-1 plan, indicating pre-planned and potentially non-insider trading related activity.
• The transactions were intended to cover tax withholding obligations, a common and often necessary reason for executives to sell shares.
• The reporting person retains a substantial number of shares, both directly and indirectly, suggesting continued beneficial ownership and alignment with the company's performance.

Negatives

• A significant number of shares (31,683 in total) were sold by a key executive.
• The sales represent a reduction in the CFO's direct and indirect beneficial ownership of the company's stock.

Risks

• Potential for negative market perception due to a high-ranking executive selling a considerable number of shares, even if under a pre-arranged plan.
• The Rule 10b5-1 plan was established in August 2025, and the current market conditions or company performance may differ significantly from when the plan was initiated.

Future Outlook

The filing does not contain forward-looking statements or guidance. It solely reports on past transactions.

Management Comments

• The sale was effected pursuant to a Rule 10b5-1 instruction letter entered into on August 8, 2025 to satisfy the Reporting Person's tax withholding obligation upon the vesting of previously granted equity awards.
• 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.

Industry Context

StockSavvy.ai notes that Form 4 filings are standard for reporting insider transactions. The use of a Rule 10b5-1 plan by Oscar Health's CFO is a common practice for executives to manage their stock holdings and tax obligations in a way that aims to avoid insider trading concerns. The healthcare and health insurance sector, in which Oscar Health operates, often sees such transactions as executives manage their compensation packages.

Stakeholder Impact

• Shareholders: May perceive the sale as a negative signal, although the Rule 10b5-1 plan mitigates insider trading concerns. Continued substantial beneficial ownership by the CFO should be noted.
• Employees: The sale is primarily related to the CFO's personal financial management and equity awards, with no direct impact on general employee compensation or benefits.
• Creditors: No direct impact from this stock transaction.
• Suppliers/Customers: No direct impact from this stock transaction.

Next Steps

• The reporting person may continue to sell shares under the Rule 10b5-1 plan if it remains active and conditions are met.
• The company may receive requests for further information regarding the specific sale prices from the SEC or security holders.

Key Dates

Keywords

Oscar Health, OSCR, Form 4, Insider Trading, Rule 10b5-1, Stock Sale, Richard Scott Blackley, Chief Financial Officer, Beneficial Ownership, Class A Common Stock, Tax Withholding