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V O L . X X V I I I N O. V I I A P R I L 4 , 2 0 2 2 22 B A N K I N G / F I N A N C E / I N S U R A N C E R oyce 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. "e 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., now 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 insur- ance 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," Cross says. e 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. en 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 com- pany 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. "e 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 acqui- sitions fell on Cross's shoulders. "When they first started acquir- ing 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 buy- out 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 inter- est 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. e 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 technol- ogy 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 Royce Cross joined the family business, Cross Insurance, in 1970 and is still at it more than a half century later. He has no plans to retire. P H O T O / J I M N E U G E R F O C U S TIME SUN Insurance scion's in the B y J e s s i c a H a l l In his sixth decade of work, Royce Cross has no plans to retire

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