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Royce Cross, Chairman of Cross Insurance is the 2024 Insurance Professional of the Year 

July 1, 2024 by Michael Pezza, Jr.

Award Will Be Presented to Royce Cross, Chairman of Cross Insurance, on October 4, 2024

Royce Cross, Chairman of Cross Insurance is the 2024 Insurance Professional of the Year 

Royce Cross, Chairman of Cross Insurance, will receive the Insurance Library’s 2024 Insurance Professional of the Year Award. Sonya Ross, the Library’s President and Board Chair, will present the award at a luncheon gala on Friday, October 4, at the InterContinental Boston.

An Expansive Career

Mr. Cross began his career at Cross Insurance in 1970, manually typing policies under the guidance of his father, Woodrow Cross, founder of the agency. Royce took on greater responsibilities over the years and was named President of the organization in 1983, later taking on the role of Chairman.

Over more than five decades, Mr. Cross has helped shape and steer his family’s namesake agency into becoming not just an insurance staple of Bangor, Maine, but one of the largest insurance providers in New England. As the result of more than 170 mergers and acquisitions, Cross Insurance now has more than 1,100 employees in more than 50 offices in Maine, Massachusetts, New Hampshire, Vermont, Rhode Island, Connecticut, New York, and Florida.

“This award is very much about my father and his contribution to the business,” remarked Jonathan Cross, CEO of Cross Insurance. “At the heart of this legendary adventure is a man that loves his business, loves this industry, and is at his best when he’s doing a deal. For several years now I have challenged others in the industry to find me someone else that loves this business more than my father, and so far nobody has yet to find one.”

Broad Range of Products and Clients

Cross Insurance provides an extensive range of insurance and financial products, including personal and commercial lines insurance, employee benefits, and surety bonds. Its customers range from individuals and sole proprietors to large private and publicly traded companies. Among its more well-known clients are the New England Patriots, the New England Revolution, and the Boston Red Sox.

History of the IPYA

The Insurance Professional of the Year Award was first made possible by the establishment in 2001 of the Richard B. Simches Fund. Mr. Simches, who founded Safety Insurance Company, believed that it was important to recognize outstanding individuals in the insurance industry. The award was created by the Library’s Board of Trustees in the tradition of an award bestowed annually from the 1950s through 1996 by the Boston Board of Fire Underwriters.

Since 2002, when the Library first presented this award, a broad cross section of members of the insurance, financial security, risk management, and legal communities has gathered to recognize an individual who demonstrates outstanding leadership and exemplifies qualities that foster commitment to, understanding of, and respect for the insurance industry.

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