Hagerty adds senior executives to advance insurance growth strategy

Hagerty has expanded its insurance leadership team with the appointments of Adam Van Loon as SVP of Insurance Distribution and Jesse McKendry as SVP of Insurance Product. The hires support Hagerty’s broader strategy to scale its specialty vehicle insurance business.

Van Loon, formerly Chief Partnerships Officer at Plymouth Rock Assurance, will lead North American distribution efforts, focusing on brokers, agents, and partnerships. McKendry, who has held roles at GEICO, Lemonade, Metromile, and Progressive, will oversee pricing, underwriting, product development, and reinsurance.

The additions come as Hagerty continues investing in distribution and product capabilities to support its next phase of growth.

The news follows Hagerty’s signing of a non-binding letter of intent with Markel for a new fronting arrangement set to begin January 1, 2026. Under the proposed structure, Hagerty will assume 100% of the underwriting and investment risk, while Markel will continue to issue policies and provide administrative services.