What sets a business apart? Service? Hard work? Integrity? All three, if you’re Cross Insurance. But unlike companies repeating robotic mottoes, Cross Insurance practices them as a lifestyle, under the guidance of its 95-year-old founder, who ensures that his lifelong example of service, hard work, and integrity is followed.
Woodrow Cross first went into business in the 1920s, hooking his pony to a cart and visiting area farms to sell seed and hand salve. At 10 years old, he reportedly regretted starting as a businessman so late in life.
He then ventured into chicken farming, buying chickens and building a chicken house. Short on feed money, he convinced a local storekeeper to extend him credit, promising to pay his bill when he sold his chickens. Woodrow was true to his word.
As a teenager, he worked with his father, who owned several businesses, right into the Great Depression. In his late teens, he entered the grocery business at his father’s store in Bradford. But when his father died three years later, Woodrow took over the store. It was challenging to keep the store alive during the Depression, but the experience had a huge impact on Woodrow’s life.
After serving in the Army in the Pacific Theater during World War II, during which time he was married, he returned home to run the store and start a family. He worked the store for several years before relocating to Bangor in 1954. In his late 30s, Woodrow wanted to establish a new career, but in the meantime supported his family through other work. One night job was at the under-construction Bangor Auditorium, ensuring it stayed heated so the new concrete would properly set. He also worked as a laborer at Eastern Fine Paper.
When someone suggested an insurance career, he liked the sound of it. He looked into buying a small insurance agency and began learning all he could about the field. Someone else bought the agency, but he continued his self-education and was soon licensed by the state to sell insurance.
Woodrow started working out of his home, seeing customers by day and doing paperwork by night at his dining-room table (and later a desk, when he could afford it). He spent time at the library and talking with insurance companies, learning all he could. His client base expanded, including some of his EFP co-workers. Many of those families are with Cross Insurance today, often the children and grandchildren of the original clients.
In 1963 Woodrow purchased his first agency, hired an employee, and moved downtown to the Coe Building on the coincidentally named Cross Street. His son Royce, aged 12 then, frequently joined his father on client visits — running to the car when his father needed certain materials, helping with the tape measure when sizing a client’s property, and serving as an all-around gopher. Along the way, he learned all about the business, and eventually joined the agency in 1970.
In 1979, Royce’s brother Brent joined the company. He’d begun in local television, but discovered his only advancement was to go into television marketing. Figuring if he were to be in sales he might as well work for the family business, he came aboard.
After moves to the old Merchants Bank building and then to Key Plaza, the agency’s real growth began in 1993 when it acquired Fenderson Insurance and its Gilman Road building in Bangor. An earlier Bangor-area acquisition had added a Lincoln branch, but with Fenderson came Calais and Eastport branches, greatly extending Cross Insurance’s reach.
Over its life, Cross has purchased about 100 small agencies, rarely pursuing sales but answering companies offering to sell. Cross spread first across Maine and recently into New Hampshire and Massachusetts. Today, with nearly 500 employees, there’s virtually no type of insurance the company doesn’t handle, and no New England industry in which it’s not involved — even handling various insurance contracts for the New England Patriots and the Boston Red Sox.
At 95, Woodrow Cross still comes to work every weekday from 7 a.m. until 4:30 p.m., and is there on Saturday. And he sets quite an example for everyone: When Royce suggests his father go home early on days when he’s tired, Woodrow refuses.
“He says, ‘No, I can’t do that; that wouldn’t be a good example,’” Royce said.
When Woodrow won an award from an insurance company and was invited to a ceremony in southern Maine, Woodrow wanted to know the night of the event, because he didn’t want to end up late to work the next morning — which the insurance company found amusing. “They came back and they said, ‘I guess that kind of tells it all right there,’” Royce said.
And Woodrow keeps working. “He told me a while ago that he’s planning on working until he’s 100, and then he’s going to re-assess the situation,” said Royce. That’s no surprise for a man who often says he wishes he had the energy he did when he was 80.
At 60, Royce is nearing retirement age, but he’s having too much fun as his job — and besides, the pressure is on. “How can I plan on retiring when my 95-year-old father, who’s planning on working to 100, [is here]?” he said with a laugh. “I can’t leave as long as he’s here.”
Royce’s son, Jonathan, got no breaks for being family. Like his father, he was the gopher, emptying trash cans and running errands. And he remembers very well what his grandfather told him the first day he went out to sell in the mid-1990s.
“My grandfather pulled me aside and said, ‘You have to understand that you’re protecting every last asset that these people have built over a lifetime,’” Jonathan recalled. “It’s a tremendous responsibility. It’s not just to sell somebody something. You’ve got to make sure that’s it’s right.”
Brent’s son, Woodrow II, is now 23 and, like Jonathan, started as a gopher in the office. And Woody also gets no breaks; family members start at the bottom, assigned to other employees, to learn the ropes. “We never interfere — we stay right out of it,” said Brent.
Like his brother, Brent loves what he does, and loves working with the family.
“Family business has its challenges, and it can also be very rewarding,” he said. “Until I started working with my son, I don’t think I knew the joy my father had felt working with his sons.”