Crestwell Underwriters

Crestwell Underwriters is a managing general agent (MGA) that launched in August 2025 with significant capital support from Bain Capital. The Tampa-based firm specializes in providing tailored, property-only insurance solutions for the commercial residential market in Florida, specifically targeting condominium associations. Its clients include property owners, boards of directors, and property managers.

The company was established to address the complex and dynamic nature of Florida's commercial residential insurance market. It operates with a business model focused on a disciplined, data-driven approach to underwriting. At its inception, Crestwell announced it would assume a portfolio of policies from Citizens Property Insurance Company, Florida's state-backed insurer. As an MGA, Crestwell's capacity is provided by partner insurers, with Emerald Bay Risk Solutions serving as an initial partner through its admitted carrier, Mainsail Insurance Company, which holds an A- (Excellent) rating from AM Best.

Crestwell is led by a veteran team with deep experience in the Florida property insurance sector. Chief Executive Officer Kathy Cody previously served as CEO of Orchid Insurance, a specialty underwriter of catastrophe-exposed property insurance. Paul DiFrancesco, the Chief Underwriting Officer, joins from GeoVera, where he was the Commercial Lines Segment Leader. Together, the leadership team brings over three decades of insurance industry experience to the firm.

Keywords: Managing General Agent, MGA, Florida insurance, commercial residential insurance, property insurance, condominium association insurance, data-driven underwriting, Bain Capital, property and casualty, P&C, admitted insurance, Citizens depopulation, commercial property, underwriting, catastrophe-exposed property, specialty insurance, insurtech, property owners insurance, board of directors insurance, property managers insurance