Form 4: Hagerty CLO Diana Chafey Reports Stock Transactions

Sentiment:

Insider Transaction Report 3 October 2025 4:16 PM

Hagerty's Chief Legal Officer, Diana Chafey, reported the acquisition of 993 shares through an ESPP and the withholding of 1,076 shares for taxes.

Summary

Diana Chafey, Chief Legal Officer of Hagerty, Inc., reported two transactions involving Class A Common Stock.
On October 1, 2025, 1,076 shares were withheld for taxes at a price of $11.95 per share, related to the vesting of Restricted Stock Units (RSUs) granted on October 1, 2023.
On October 2, 2025, 993 shares were acquired through the Hagerty, Inc. Employee Stock Purchase Plan (ESPP) at a price of $11.35 per share.
The ESPP acquisition price represents 95% of the closing price on October 1, 2025, for the offering period of April 1, 2025, through September 30, 2025.
Following these transactions, Diana Chafey beneficially owns 56,934 shares of Class A Common Stock.

Sentiment

Score: 6

Explanation: The sentiment is neutral to slightly positive. While shares were withheld for taxes, a significant number of shares were also acquired through an employee purchase plan, indicating continued executive investment in the company.

Positives

Acquisition of 993 shares through the Employee Stock Purchase Plan (ESPP) indicates continued investment by a key executive.
The ESPP purchase price of $11.35 per share represents a 5% discount from the market price, benefiting the executive.

Negatives

1,076 shares were withheld for taxes upon RSU vesting, which reduces the executive's direct shareholding from that specific vesting event.

Future Outlook

Industry Context

Corporate Governance

Change Type	Description	Effective Date	Impact Assessment
Delegation of Authority	Diana Chafey, Chief Legal Officer, has granted a Power of Attorney to John Armbruster, Kieron Lake, and Tracey Derenzy to prepare, execute, acknowledge, deliver, and file Forms 3, 4, and 5 on her behalf with the SEC.	2025-05-08	Streamlines the process for executive compliance with Section 16(a) reporting requirements, ensuring timely and accurate filings.

Stakeholder Impact

Shareholders: Provides transparency into executive stock ownership and transactions, which can be a signal of management's confidence in the company.
Employees: The Employee Stock Purchase Plan (ESPP) allows employees, including executives, to acquire company stock at a discount, aligning their interests with shareholders.

Key Dates

Date	Description
2023-10-01	Grant date of Reporting Person's RSU award agreement.
2025-04-01	Start of the ESPP offering period.
2025-05-08	Date Power of Attorney was executed by Diana Chafey.
2025-09-30	End of the ESPP offering period.
2025-10-01	Transaction date for shares withheld for taxes upon RSU vesting.
2025-10-02	Transaction date for shares acquired through the ESPP.
2025-10-03	Date the Form 4 was signed.

Recommendation

hold

This Form 4 filing details routine insider transactions, specifically RSU vesting with tax withholding and an ESPP share acquisition. These are standard events for executives and do not provide new fundamental information to warrant a change in investment thesis. The acquisition through ESPP shows continued executive alignment, but the overall volume is not significant enough to signal a strong 'buy' or 'sell' opportunity. Therefore, a 'hold' recommendation is appropriate as this filing does not alter the underlying investment case for Hagerty, Inc.

Keywords

Hagerty Inc, HGTY, Diana Chafey, Chief Legal Officer, Form 4, Insider Trading, Stock Transactions, ESPP, RSU Vesting, Share Acquisition, Share Withholding

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