Jonathan Cross succeeded his father Royce Cross, to become president and CEO of Bangor-based Cross Insurance. Jonathan Cross is the thrid generation of his families to serve as president since his grandfather founded the business in 1954. Credit: Courtesy of Cross Insurance

The new CEO of Cross Insurance says he anticipates that the Bangor-based agency that has already grown into one of the largest insurance providers in the Northeast will continue to expand into new parts of the country in the coming years.

Cross Insurance said this week that Jonathan Cross has taken over as CEO of the company his grandfather, Woodrow Cross, started in 1954. Jonathan Cross, who already was the company’s president, succeeds his father, Royce Cross, as CEO. Royce Cross will continue to serve as the business’ chair.

Cross Insurance has grown, largely through acquisitions of smaller insurance agencies, to employ 1,000 people working in more than 50 offices in eight states. Its clients include some of New England’s top athletic teams, and both the Cross Insurance Center in Bangor and the Cross Insurance Arena bear the business’ name.

Cross, who was born in Bangor and raised in Brewer, began running errands for the company after he turned 16, then became a licensed insurance agent after earning a bachelor’s degree in business administration from Husson University — then Husson College — in 1998.

Though he took over the title of CEO from his father, Cross said his father is not considering retirement.

“My father by no means plans on slowing down or stepping back,” Cross said. “He loves the business, loves coming in every day and plans on staying very active in the business.”

Today, though it’s headquartered in Bangor, the company can operate primarily over the phone and online, meaning its agents can serve thousands of clients across the country, Cross said.

At a time when large insurance companies are making tasks like submitting payments and filing claims increasingly easy as technology advances, Cross said local insurance agents are still critical.

“When someone is looking to buy their first home, they like to have someone on the other end of the line or in person that they can talk to,” Cross said. “It’s a job where you’re helping people navigate a very complex marketplace with confusing products.”

In his tenure as president, Cross said he anticipates seeing the business continue to grow, both organically and by acquiring other businesses, and both locally and into new parts of the country. He said he sees an opportunity for growth in a generation of insurance agents who are aging out of the industry, creating opportunities to acquire the businesses they’re leaving.

Cross said the business tries to entice young people to join the insurance industry by offering a summer internship program and reaching out to schools in Maine and New England. The company also looks for people in similar industries with transferable skills who can be taught insurance if they’re interested.

“It’s amazing how many people love what they do but it’s not something they grew up thinking they were going to do,” he said. “Insurance is an industry that people don’t seek out but it finds them. It has proven to be a very stable industry, though it’s not without its challenges, but everybody needs insurance. You don’t have to be on the phone every day selling insurance to work in the industry.”

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Kathleen O'Brien

Kathleen O'Brien is a reporter covering the Bangor area. Born and raised in Portland, she joined the Bangor Daily News in 2022 after working as a Bath-area reporter at The Times Record. She graduated from...