For insurance scion Royce Cross, after 52 years in business, it's his time in the sun

File photo / Jim Neuger Royce Cross, who joined Cross Insurance in 1970, stepped down as CEO in 2022 and now serves as chairman.

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By Jessica Hall

Royce Cross, president and CEO of Bangor-based Cross Insurance, starts work in the wee hours of the morning, writing emails. He saves them and sends them out later in the day to avoid questions about why he was working at such early hours.

“The time stamp was embarrassing,” he says.

Cross has been working all hours of the day since 1970, when he joined the company his father started at the family’s kitchen table in 1954. His father, Woodrow Cross, was still a presence in the Cross Insurance offices well into his late 90s and died in 2020 at age 103.

Cross Insurance, a subsidiary of Cross Financial Corp., is now the largest independent insurance provider in New England, and has a presence in New York and Florida. It boasts about 1,000 employees in more than 50 offices, serving 100,000 customers. It’s the official insurance partner of the Boston Red Sox, New England Patriots and Boston Bruins.

“When I first started, my father encouraged me to try it. But he also said you shouldn’t work at a job you don’t like. I was mostly looking for a job, but I ended up with a career. I took it because I needed a job. I needed work. But I find it very exciting,” says Cross, 70.

The company has quietly grown through more than 175 acquisitions.

“We’ve been doing this for years and years. Buying companies every year. People just notice it more today,” Cross says. “We used to go out and borrow a pickup truck and a dolly to pick up file boxes. Now it’s all done electronically and we have entire teams dedicated to making acquisitions go smoothly.”

Looking for the right opportunities

Cross gets approached about buying agencies all the time, but it’s all about the right people and the right place, he says.

“If it’s a location we want to be in, then we take a look. We look at the talent they have in place. It’s all about the people. Then we look at the book of business and see if it is the kind we want,” Cross says. “It’s been a good run. We look for honest, decent people who do what they care about.”

Only once did Cross say the company made a misstep in an acquisition. Cross attributed the problem to failing to properly check out the reputation of the agency before the deal. Cross Insurance sold the agency quickly and then later bought the combined agency that they sold it to.

“The problems had been fixed and we went and bought the whole thing,” Cross says.

Melanie Campbell, who recently retired after 42 years of working at Cross Insurance, says much of the pressure and challenges of integrating so many acquisitions fell on Cross’s shoulders.

“When they first started acquiring agencies, his father was excited by it. But it was Royce who had to get it done. Bringing the offices together, acclimating the new staff, adding sales people, remodeling office space — it was Royce’s job to make it work,” Campbell says. “And he was great at it.”

Does the serial-acquirer ever get buyout offers himself?

“Constantly. A week never goes by where we don’t get a phone call or an email,” Cross says. “But I have no interest in it. We like what we do. I’m pleased that someone asks you out, but you don’t have to go to the dance,” Cross says. “Besides, it’s a family affair.”

‘Comfort and reassurance’

Royce Cross’s father, Woodrow Cross, left the office in 2016. The elder Cross was born on a small farm in Bradford. In his obituary, it was noted that that “Woodrow’s entrepreneurial spirit was apparent at an early age when he sold seeds door to door to other farmers at the tender age of six. As a teenager he raised and sold chickens.” He was born before Bradford had electricity, phones or paved roads, the obit noted, yet later as an executive he embraced technology and automation.

“My father,” Cross pauses. “I was very fortunate. I deeply miss him.”

“I miss his insight. As recently as this morning I said to myself ‘If my father were here, my father would do this.’ I miss that a lot. He gave me a lot of comfort and reassurance. ‘We can do it,’ he would say and that would give me courage. He was enthusiastic,” Cross says.

“We’re a lot larger today. The company has continued to grow in his absence,” Cross says.

Photo / Jim Neuger

Royce Cross joined Cross Insurance in 1970.

Cross has a nephew and son in the business and one of his grandchildren talks about joining the business someday, but Cross laughs and says, “Who knows?”

“His father was a legend. He emulates the behavior of his father. His son emulates him. You can see it in their daily interactions,” says Pete Vigue, chairman of construction firm Cianbro, who has worked with Cross for decades.

“The man works an endless amount of hours a week. And he still takes time for his family and grandchildren. He wants to be normal people. They may have nice things but not boastfully. I consider him to be a real person,” Vigue says.

In the off hours, the Cross family talks business, of course.

“It’s only natural. I have an easy chair I sit in that I’m always working in at home. When you love what you do, it’s not work,” Cross says.

When he’s not working, which is rare, Cross loves Disney and has been more times than he can count. He even had a Disney pen in hand during the interview.

He also likes four-wheeling on the few hundred acres behind his home in Brewer.

“I find every animal out there. I even saw a bobcat wander through. Every creature Maine has,” Cross says.

Campbell says Cross is all about work, home and family.

“He works. He doesn’t play. He gets that naturally. His father was the same way,” Campbell says. “He loves his home and family. He loves his land in Brewer. He takes his chainsaw and cuts trees to build paths. If he does go on vacation, it’s to Disney. But if he stays a whole week — that’s a long week. If a customer has a big loss, he’d jump on a plane and come home early to handle it.”

Working with the Patriots

Being a family-owned firm helped Cross gain some high-profile clients, such as New England Patriots owner Robert Kraft.

“Robert prefers working with family business. It’s really wonderful how they’ve supported family businesses through the years,” Cross says.

“It started out as Kraft wanting to partner with us. I thought ‘Partner with us? Hmmm. OK. Let’s partner.’ Then they said, ‘Maybe.’” Cross laughs. “So, we started with them modestly and kept building on that.”

Cross now has a dedicated team that works with Kraft’s interests ranging from sports to personal to real estate holdings.

Clients, big or small, become intimately connected with Cross Insurance, Cross says, because insurance gets intertwined intimately with people’s lives and livelihoods.

“People don’t care about insurance until something goes wrong. When you have something happen, it’s extremely personal. If someone’s hurt, it’s very personal. If a house is lost, it’s someone’s world,” Cross says.

When asked what’s next for the company, Cross shrugs.

“We’ve never had five- or 10-year plans. We’ve never done that. We’re more opportunistic,” Cross says.

“Insurance doesn’t seem to have peaks and valleys that other industries see. During COVID, everyone still purchased car insurance and home insurance. We always seem to have business to do. It provides good stability,” Cross says.

The industry competition has become fierce, Cross says, as insurance can be bought anywhere in the world from a computer or phone.

“Without technology, we wouldn’t be where we are. Technology introduces competition but also opens up the world to us. We’re part of that competition,” Cross says.

Cross says he enjoys his job too much to ever think of retiring.

“I have no plans to go anywhere. I enjoy what I do. What’s my end game? I’m living my end game,” Cross says.

“I never look back at life. Yesterday is gone. There’s far more opportunity today than there’s even been in the business,” Cross says. “There’s no better time in history to live, and no better industry than this business. No better place to live in America. The kind of opportunity that exists for my family, there’s nowhere else in the world I’d rather be,” Cross says.