Form 4: Hagerty Inc. Insider Trading Activity Reported

Diana Chafey, Chief Legal Officer of Hagerty, Inc., reported transactions involving Class A Common Stock, including acquisitions through RSUs and ESPP, and tax withholdings.

Summary

• Diana Chafey, Chief Legal Officer at Hagerty, Inc., has filed a Form 4 detailing transactions in the company's Class A Common Stock.
• These transactions include the acquisition of 23,742 shares underlying restricted stock units (RSUs) under the 2021 Equity Incentive Plan, which vest annually until April 1, 2029.
• Additionally, 4,833 shares were withheld for taxes upon the vesting of RSUs.
• Chafey also acquired 1,165 shares through the Hagerty, Inc. Employee Stock Purchase Plan (ESPP) for the offering period ending March 31, 2026, at a price of 95% of the closing price on April 1, 2026.

Sentiment

Score: 5

Explanation: StockSavvy.ai views this as a neutral filing, as it primarily reports routine insider transactions related to compensation and employee stock purchase plans, without providing new financial performance data or strategic outlook.

Positives

• Acquisition of 23,742 shares through RSUs indicates continued equity-based compensation and alignment with company performance.
• Purchase of 1,165 shares via ESPP demonstrates employee participation and investment in the company's stock.
• The transactions reflect active engagement of a key executive with the company's equity.

Negatives

• Withholding of 4,833 shares for taxes upon RSU vesting represents a reduction in the net shares received by the reporting person.

Risks

• The RSUs are subject to continued service with the Issuer, with exceptions for death, disability, retirement, or a change of control, indicating potential forfeiture under certain circumstances.
• The ESPP purchase price is tied to the stock's closing price, meaning the cost could fluctuate.
• The filing is a Form 4, which reports insider transactions and does not inherently contain forward-looking statements about the company's future performance or risks.

Future Outlook

This filing is a Form 4 reporting insider transactions and does not contain forward-looking statements or guidance from the company.

Industry Context

StockSavvy.ai notes that Form 4 filings are standard disclosures for insider transactions and reflect individual executive actions rather than company-wide strategic updates. The reported RSU and ESPP activity is common within the financial services and insurance sectors as a method of executive compensation and employee engagement.

Stakeholder Impact

• Shareholders: The transactions reflect executive compensation and employee investment, which can indirectly influence long-term shareholder value through executive motivation and retention.
• Employees: The ESPP participation indicates an opportunity for employees to invest in the company.
• Management: The RSU grants and ESPP purchases are part of the compensation structure for key executives like Diana Chafey.

Next Steps

• RSUs acquired under the 2021 Equity Incentive Plan will continue to vest in equal amounts on each annual anniversary of the grant date, ending on April 1, 2029, subject to continued service.
• Future tax withholdings will occur upon subsequent RSU vestings.

Key Dates

Keywords

Hagerty Inc., HGTY, Form 4, Insider Trading, Class A Common Stock, Restricted Stock Units, RSU, Employee Stock Purchase Plan, ESPP, Chief Legal Officer, Diana Chafey, Equity Incentive Plan, Securities Exchange Act