Form 4: Oscar Health CEO Bertolini Trades Shares

Oscar Health CEO Mark T. Bertolini reported transactions involving Class A Common Stock and Performance Restricted Stock Units.

Summary

• Mark T. Bertolini, CEO and Director of Oscar Health, Inc. (OSCR), reported transactions on April 3rd and April 6th, 2026.
• On April 3rd, 2026, 5,733,334 Performance Stock Units (PSUs) vested, which are contingent rights to receive Class A common stock.
• On April 6th, 2026, 1,000,001 shares of Class A Common Stock were withheld by the issuer to cover tax obligations related to PSU settlement.
• Also on April 6th, 2026, 1,000,000 shares of Class A Common Stock were purchased by Bertolini in a private placement.
• Following these transactions, Bertolini beneficially owns 10,196,877 shares of Class A Common Stock directly.

Sentiment

Score: 5

Explanation: StockSavvy.ai views this as a neutral filing, as it primarily details standard executive compensation and tax-related share transactions rather than significant new strategic initiatives or financial performance indicators.

Positives

• Vesting of 5,733,334 Performance Stock Units indicates achievement of performance targets.
• Purchase of 1,000,000 shares of Class A Common Stock in a private placement demonstrates continued investment by the CEO.
• Direct beneficial ownership of 10,196,877 shares shows significant alignment of CEO's interests with shareholders.

Negatives

• 1,000,001 shares were withheld by the issuer to satisfy tax obligations, representing a disposition of potential shares.
• The filing details transactions related to executive compensation and tax liabilities, which are standard but represent a reduction in immediately available shares.

Risks

• The settlement of remaining PSUs and restricted stock units, along with sales to cover resulting tax obligations, will occur at a later date, subject to a 10b5-1 plan.
• Potential future sales of shares to cover tax obligations could impact the stock price if executed in large volumes.

Future Outlook

The settlement of remaining PSUs and restricted stock units, along with sales to cover resulting tax obligations, will occur at a later date in accordance with a 10b5-1 instruction letter.

Industry Context

StockSavvy.ai notes that insider transactions, particularly those involving stock purchases by executives, can be viewed as a signal of confidence in the company's future prospects. The details of this Form 4 filing provide insight into the compensation structure and executive's personal investment strategy within the health insurance technology sector.

Stakeholder Impact

• Shareholders: The CEO's purchase of shares may be viewed positively, indicating confidence. However, the withholding of shares for taxes and potential future sales could have minor impacts on share availability.

Next Steps

• Settlement of remaining PSUs and restricted stock units at a later date.
• Sales of shares to cover resulting tax obligations at a later date, as per 10b5-1 plan.

Key Dates

Keywords

Oscar Health, OSCR, Form 4, Insider Trading, Executive Compensation, Stock Options, Performance Stock Units, Class A Common Stock, Beneficial Ownership, SEC Filing, Mark T. Bertolini