Hagerty reveals new chief legal officer

She assumes the role as predecessor retires

Hagerty reveals new chief legal officer

Insurance News

By Mika Pangilinan

Specialty insurance provider Hagerty has appointed Diana Chafey (pictured) as its new chief legal officer.

In this role, Chafey will join the senior leadership team and contribute to strategic, management, and policy decisions. She will also assume responsibility for overseeing legal, compliance, governmental, and regulatory matters, as well as provide advice and counsel to Hagerty’s CEO, leadership team, and board.

A legal executive, Chafey joins Hagerty with over 25 years of experience. She has advised senior executives and boards of directors on complex legal, compliance, and risk management issues in heavily regulated industries. This includes representing domestic and international insurers, reinsurers, intermediaries, and service providers in transactional and regulatory matters within the insurance space.

Chafey most recently held the position of chief legal officer and corporate secretary at ATI Physical Therapy, a publicly traded rehabilitation provider specializing in physical therapy, workers’ compensation, rehab, and employer worksite solutions. Before that, she was executive vice president, chief legal counsel, and corporate secretary for The Warranty Group (TWG Holdings Limited). She also held roles at Interstate Insurance Group and Jefferson Insurance Group, in addition to serving as partner at DLA Piper USA LLP.

“Based on Diana’s deep knowledge of the insurance industry, global experience and expertise working with complex regulatory and compliance matters, she is a valuable asset to Hagerty’s future growth and profitability,” said CEO McKeel Hagerty. “I am confident she will provide excellent strategic guidance to our organization as we enter a new phase of our growth arc.”

“I have admired Hagerty and its passion to cultivate and preserve the collector car ecosystem for many years,” added Chafey. “I look forward to joining Hagerty and supporting the company’s business and growth objectives to create value for stakeholders while enhancing and protecting shareholder value.”

Hagerty announces Barbara Matthews’ retirement

Chafey’s appointment comes as Barbara Matthews retires from Hagerty after holding the role of general counsel and senior vice president of legal since 2007.

Matthews will be assuming a senior advisor role through the end of 2023 to ensure a smooth transition, Hagerty said in a press release.

“On behalf of the board of directors and leadership team, we are incredibly grateful for Barbara’s work throughout her tenure at Hagerty,” said Hagerty. “From the many complex partnerships we forged over the years with the nation’s largest insurance companies to helping us establish an independent board of directors and shepherding us through the complicated process of becoming a publicly traded company, Barbara has always been a steady and trusted advisor.”

"I am proud of the role I have played in helping Hagerty grow and flourish as a company,” said Matthews. “We had big dreams when I started here in 2007 and it has been gratifying to see them come to fruition. I want to thank the Hagerty family, the board of directors and everyone that I have had the honor to work with over the years. It has truly been a rewarding experience.”

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