Royce Cross is stepping down as CEO of Cross Insurance and is being succeeded by his son, Jonathan Cross.

man in white shirt and navy blazer at a table

Jonathan Cross

As president and CEO, Jonathan Cross will oversee the strategic growth and planning of the 68-year-old, family-owned insurance agency, the Bangor-based company said in a statement Friday.

Cross has served as president since 2020 and has “played a critical role in the expansion of Cross’s insurance services and capabilities,” the company said. Royce Cross will now serve as chairman.

Cross Insurance, a subsidiary of Cross Financial Corp., is the largest independent insurance provider in New England with about 1,000 employees and more than 50 offices, serving 100,000 customers. Cross is the official insurance partner of the Boston Red Sox, New England Patriots and Boston Bruins. The Cross Insurance Arena in Portland and the Cross Insurance Center in Bangor both carry the company’s name.

“Our agency is extremely proud of our ongoing legacy and there is no one better suited than Jonathan to carry us forward as we continue towards our long-term strategic goals,” Royce Cross said in a statement. “Jonathan’s personal values of integrity and hard work, along with his business acumen and vision of where our agency is headed exemplify the leadership skills that will make him successful in this new role.”  

Jonathan Cross is the third generation of the Cross family to lead the company. His grandfather, Woodrow Cross, launched the business in 1954 and continued serving with it until about a decade ago. Woodrow Cross died in 2020 at 103.

“For six decades, my grandfather guided this company from its start with his legendary work ethic and inspiring entrepreneurism. He had incredible vision for business, community and an understanding of the right thing to do,” Jonathan Cross said. “My father has closely followed that example in his decades as chief executive of the company. Under my father’s leadership, we’ve created a family-driven culture while establishing ourselves as one of the largest insurance brokers in the country. I am proud to have the opportunity to continue in that tradition.”

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