Woodrow Cross


About Woodrow

Over the last six decades, Woodrow Cross has built Cross Insurance into the largest independent insurance agency in New England, and one of the largest in the nation.

Hard work and perseverance have been part of Woodrow Cross’ life since he was a small boy, growing up on a farm in the small town of Bradford, ME.  At 6-years-old, Woodrow started his first business of selling seeds door-to-door.  He then started to take out small loans to purchase day-old chicks, and would sell them for a profit once they matured.  And later, he worked in his father’s general store, hauling huge blocks of ice up a ramp to a storage bin – a task that tested the strength of grown me.  Simply put, Woodrow was born to be a businessman and raised to be a hard worker.

During the Great Depression, Woodrow’s father suddenly passed away, leaving Woodrow, at 21-years-old, in charge of the general store his father owned.  After years of operating the store and then serving in World War II in the Pacific theater, including campaigns in New Guinea and the Philippines, as well as occupation duty in Japan, Woodrow married his wife, Janette.

The two raised a family of three sons and two daughters.  The family moved to Bangor, where Woodrow started Cross Insurance.  He started the company at his kitchen table, and worked from there for the next nine years, until hiring employees and moving to downtown Bangor, from where the company continued to grow.

Over the decades, Woodrow Cross established a reputation throughout the industry.  John Leonard, President and CEO of Maine Employer’s Mutual Insurance Company, said that Woodrow is “a legend in our business,” and that “there’s hardly anyone in Maine who’s been able to match his success.”  Leonard then spoke of the company Woodrow has created and said, “It’s an extremely well-run agency that excels in customer service, and that kind of culture doesn’t happen by accident.”

Despite his 98 years of age and 61 years in the business, Woodrow still plays an active role in day-to-day activities and remains Chairman of the agency.  He has been able to keep adapting to change, and often leads the management team into new ventures, particularly on the automation front. “His work and his family are what keep him going,” said one of his employees.

Family is important to Woodrow, and he considers himself a fortunate man to have two sons, Royce, President, and Brent, Executive Vice President, working with him each day.  Two of Woodrow’s grandsons also work with him in the Bangor office, Jonathan, Executive Vice President, and Woodrow, Commercial Lines Account Executive.

While proud of the business he has been able to build – a mainstay of the Bangor area economy, and respected throughout the region – Woodrow doesn’t minimize the skills and dedication that are needed to stay competitive.

“It’s very easy to get discouraged,” he said, “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.”