Maine Trails, April - May '08
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No simple proposition

Woodrow Cross built an insurance leader with hard work and common sense

By Douglas Rooks

When woodrow cross, chairman of Cross Insurance, comes in every morning at 7 a.m. to open the office, he is maintaining a ritual he’s observed for 54 years since he opened a one-man insurance agency in his home in 1954.

“I couldn’t afford an office back then,” he recalled in a recent interview at the spacious building near the Bangor Mall that Cross Insurance has called home for the past 15 years.

Things have certainly changed since those humble beginnings. Cross Insurance is now the largest independent agency in Northern New England, and one of the largest in the country. It has 350 employees, including 50 at the Bangor home office and 27 offices and affiliates in Maine and New Hampshire.

Cross Insurance has been a member of the Maine Better Transportation Association for many years, reflecting its instrumental role in providing the surety bonds necessary to accomplish major transportation projects.

The company’s growth has been fueled by acquisitions of independent agencies, more than 60 to date. “We expect to close on four more this month,” he said.

Cross, now 91, keeps a low profile. He has a corner office, but it is small, spare and orderly, reflecting his personality and single-mindedness. There are photos of his grandchildren and an honorary degree from Husson College on the stark, white walls. Cross’ presence is keen and composed as he considers questions and speaks in a calm, methodical way.

Asked about the secret of the extraordinary success of his agency, there is a simple answer: “Hard work.”

Keeping pace

Cross not only comes in at 7 a.m. every morning, he stays until 5 or 5:30 p.m. in the evening. He used to work evenings and weekends – anything necessary to sustain and improve the business. “I didn’t mind,” he said of the long hours. “I was always prepared to do what was necessary.”

“He usually turns the lights on in the morning, and turns them off in the evening,” said Alice Dyer, vice president of operations, who’s been with the company since 1985.

Cross doesn’t expect employees to match his pace, “but you’re rewarded if you do,” said Melanie Campbell, vice president of commercial lines, a Cross employee since 1979.

The agency is very much a family company and representatives of three generations are actively involved in the business. Two sons are among the officers – Royce, the eldest, is president and CEO, and Brent is executive vice president. Royce’s son, Jonathan, is a vice president and Brent’s son, Woodrow II, plans to join the company full time after he completes his studies at the University of Maine. Jonathan and Woodrow II (“Woody”) represent the third generation to be involved in the family business. Frank Ferland, the COO, joined the company from outside the family in 2001.

The Cross work ethic is strong in all three generations. Even Woody, who works at the agency part-time while in school, puts in long hours. He picks up the mail every morning and helps open the office with his grandfather. He returns at the end of the day after class to make sure the mail is delivered to the post office. Following their father and grandfather’s example, however, is no easy road at Cross Insurance. “They’ve earned their way aboard,” said Sandra Phinney, personal lines vice president. “They had to live up to some high standards.”

Continually investing in the company and its people is a commitment the Cross agency chooses to keep, said Ferland. Since he joined the agency seven years ago, it has more than doubled in size. “There isn’t the pressure of quarterly earnings, so you can invest in the company and its people when you choose to, and it is a great place to work for that reason,” said Ferland.

Sweet beginnings

When Woodrow Cross is asked about how he decided to get into the insurance business, he mentions his wartime experience in the 1940s, when he served in the New Guinea and Philippine campaigns, and then occupation duty in Japan. According to Brent Cross, “We hear about the war and the jungle almost every day.”

But he more often reverts to his early boyhood as an eldest son on a farm in Bradford, the still-small town on “the main road between Bangor and Milo,” now Routes 11 and 221.

Cross grew up after World War I amid the daily chores and patterned life characteristic of a rural Maine farm at the time. There were 10 cows, and he was disappointed when he couldn’t milk them as quickly as the men who were hired hands.

When he was six, his father gave him a pony that he got to ride and play with. “He was kind and gentle,” Cross said, and a good companion for a rural Maine boy. But this was business, too. The pony and a two-wheeled cart were the basis for a business making maple syrup deliveries, an important product for Maine farms.

The delivery route led to a rare misadventure when empty syrup cans began clattering in the cart and spooked the pony. “He took off and the cart wheel hit a rock and came off,” Cross recalls. He and his younger brother were left behind as the pony disappeared into the distance. “We found him back at the barn, waiting for us.”

When he was 12, the family opened a general store, and the hours were even longer. Cross remembers one of the toughest jobs was lifting huge blocks of ice – representing refrigeration, before electricity – onto a ramp leading to a small opening in a wall. The 30-by-18-inch blocks could tax the abilities of a grown man, so Cross and his brother had to maneuver them carefully. “We didn’t always succeed,” and when they crashed to the floor, he said, “we had to start all over again.”

Six hundred chicks

When he was 21, his father died suddenly, leaving the family deep in debt. It was the Great Depression. Stores typically offered credit to many customers, and “my father had a hard time saying no.” By the time of his death, the store shelves were almost bare, as suppliers began refusing to deliver.

Brent Cross said this was a difficult time for the family. His grandmother was devastated by her husband’s death, and it fell to Woodrow and his younger brother, Leon, to keep things going.

“There were lots of bills,” Woodrow Cross said. “The hospital, and the wholesalers and an awful lot of people in town.”

But Woodrow had already shown signs of a knack for business. He bought 600 day-old chicks at a time – “they were cheap then, not even a penny” – and raised them until they could be marketed. He borrowed $100 at a time, and always turned a profit while repaying the loan.

He took the same approach to the general store, negotiating payments with everyone who was owed. “It was sometimes only $5 a month, but they all got their money,” he said. He never considered bankruptcy, or, as he calls it, “going to probate,” but was always careful with his own money, and that of his business.

A friend who wrote insurance talked to him about buying his agency, and Cross at first wasn’t interested. “I knew nothing about the business,” he said. Yet the more he thought about it, the prospect of regular hours and time with his growing family had appeal. The deal fell through – his friend’s wife didn’t favor the sale – but he set up on his own shortly after.

Postwar boom

The post-war era was a good time to get into the business, said John Leonard, the veteran Traveler’s executive who became the first, and so far only, president of the Maine Employer’s Mutual Insurance Co., that writes most of the worker’s compensation business in Maine.

“The economy was expanding, the veterans were home, and there were opportunities,” Leonard said. The expansion of the highway system led to more driving, and the need for auto insurance. Meanwhile, the boom in home ownership made property insurance a big item, as well. “What we now know as the modern insurance business was largely created at that time,” he said.

Woodrow Cross was one of the most prominent of those in his generation, Leonard said. “There’s hardly anyone in Maine who’s been able to match his success. It’s an extremely well-run agency that excels in customer service, and that kind of culture doesn’t happen by accident.” He said that Woodrow Cross “is a legend in our business.”

Cross does not favor a lot of fuss. It was only recently that he was named to a business hall of fame, and received the honorary degree from Husson College. He attended back when it was the Maine School of Commerce, and studied with Chesley Husson himself, including mathematics and salesmanship. “I took all the courses I could, and learned all I could,” he said.

One of his first business purchases was a second-hand Royal typewriter that he used to write all his policies – “It was $102, including $2 for sales tax.” Two traveling representatives from The Hartford took an interest in him, and the company is still among many Cross Insurance does business with.

After a few years in insurance he was offered a job in a Bangor agency and was tempted. “It would have been easier, but I wasn’t sure it was the right move.”

He turned down the offer, but it again got him thinking about how to build his business. He bought his first agency in 1963, and housed the growing business in a succession of downtown offices before moving out to the mall area.

Modern risks, modern challenges

Insurance may seem like a simple proposition to some, he said, “But there’s a lot to it. It takes a lot of knowledge, and a lot of experience to do it right.”

Cross is proud that, when asked to write a policy to cover a business temporarily operating in Iraq, they were able to pull it off. “There was coverage for kidnap and ransom payments, and all sorts of things that agencies don’t usually cover,” he said. “We insure multi-million homes, and lots of things in between.”

He knows from experience both ends of the insurance spectrum. “I’ve had a small agency and a large agency, and it’s much better to have a large agency.”

The prospect of retirement doesn’t enter his mind. His wife died in 1992, and it is the business that keeps him going, said Melanie Campbell. “That, and family, are the things he lives for.”

Yet he is far from set in his ways, and it is his ability to adapt that most impresses his employees. Sandra Phinney said, “One of the amazing things about him it that he’s not afraid of change. When we had our last major computer conversion in December, he was the one leading. He knows what it takes to keep going.”

Cross said that running a business, small or large, is always going to be demanding. “It very easy to get discouraged, but I always tried to figure out the problem. I didn’t run from it, and if I needed help, I’d get it. And if I needed to do more work, I did it.”

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