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September 9, 2022

Royce Cross steps down as CEO of Cross Insurance; Jonathan Cross succeeds him

Photo / Jim Neuger Royce Cross, who joined Cross Insurance in 1970, will step down as CEO but be chairman of the company.

Cross Insurance, one of the largest independent insurance providers in the Northeast, said Friday afternoon that Royce Cross will step down as CEO, to be succeeded by son Jonathan Cross.

Jonathan Cross will be just the third CEO the Bangor-based Cross Insurance, one of the largest independent insurance providers in the Northeast, has had since 1954. He has served as president since 2020.

Going forward, Royce Cross will serve as chairman.

The company was founded by Woodrow Cross at his kitchen table and remains family owned to this day. Woodrow Cross continued to come into the office into his 90s and died in 2020 at age 103. 

Royce Cross, who is in his 70s, started at the company in 1970. He has continually said he will come into the office as long as he's still enjoying it. 

In an interview with Mainebiz earlier this year, he said "I have no plans to go anywhere."

Though he is at the office every day, he told Mainebiz he enjoys visiting Disney and, in Maine, enjoys four-wheeling on the land behind his house in Brewer.

In a meeting with Mainebiz earlier this year, Royce Cross said the company was built by buying smaller agencies. The policy was that you would never pay more than you would for the average starter home, he said at the time. 

In the company's press release Friday, Royce Cross said: “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. 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

Jonathan Cross is the third generation of the Cross family to oversee the company and has served as president since 2020.

Courtesy / Cross Insurance
Cross Insurance acquires North Andover-based Patriot Benefit Solutions Insurance Agency. Shown here is Cross Insurance CEO Jonathan Cross.

He first started working for the family’s business part time when he was young helping with numerous projects at the Bangor headquarters, and then became a full time licensed agent after graduating from Husson University in 1998.

He worked for many years alongside his grandfather and company founder Woodrow W. Cross, his father Royce, late uncle Brent, and cousin Woodrow Cross II, according to the news release. Jonathan Cross, who was born in Bangor and grew up in Brewer, is married with two kids. 

As an integral part of the Cross team, he has played a critical role in the expansion of Cross’s insurance services and capabilities, which now span beyond the Northeast and count roughly 1,000 employees, working in more than 50 offices.

“I am excited to lead Cross Insurance in its next phase,” Jonathan Cross said in the news release. “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. 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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