For 100-Year-Old Founder of Cross Insurance, Success Story is a Classic

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Below is the lead story from the Portland Press Herald on January 16th, 2017.  To see the full article, pictures, and a timeline of Woodrow’s life, click here to visit the Portland Press Herald.


BANGOR — Woodrow Cross, founder of Cross Insurance in Bangor, still plays an active role in Maine’s largest independently owned insurance company, visiting the office at least twice a week to offer advice and encouragement to staff.

Not bad for a guy who just celebrated his 100th birthday.

“To put it into perspective, his grandfather fought in the Civil War,” Cross Insurance President and CEO Royce Cross said about his father. “He was born during World War I. He was 12 years old when Wyatt Earp died.”

The Portland Press Herald interviewed the venerated entrepreneur Friday at Cross Insurance headquarters on Main Street in Bangor, next door to the large sports and entertainment venue that bears the company’s name. Woodrow Cross founded the insurance company in 1954, and it has since grown to more than 800 employees working out of 42 locations in five states. The company has $1.5 billion in premiums under management, making it one of the biggest insurance companies in New England.

Although his role in the business is more limited these days, Woodrow Cross remains a licensed insurance agent in Maine. Cross said that when he visits the office, he makes the rounds to talk with staff and offer his help.

“I like to meet the folks and let them know I’m there, and that I’m part of the organization still,” he said.


Cross started his first business venture when he was just 6 years old, selling seeds door-to-door in his hometown of Bradford.

By the time he was 10, he had transitioned into chicken farming. Even as a child, he began taking out small loans to purchase baby chicks, which he sold at a profit when they matured, allowing him to repay his creditors and grow the enterprise.

In his teens, Cross began working in his father’s general store, which he said further strengthened his work ethic and family values.

At 21, in the midst of the Great Depression, Cross’ father died, and he took on the responsibility of running the business and caring for his family. Cross said the challenge of keeping the business vital during such a difficult economic period had an impact on him that would last a lifetime.

“It’s very easy to get discouraged, but I always tried to figure out the problem,” he said. “I didn’t run from it, and if I needed help, I’d get it. If I needed to do more work, I did it.”

When the U.S. entered World War II, Cross enlisted in the Army, serving in the Pacific Theater with campaigns in New Guinea and the Philippines, as well as occupation duty in Japan. During that period he also married his wife, Janette, and began raising a family that grew to three sons and two daughters.

After he was discharged from the service, the Cross family relocated to Bangor. Cross worked various construction jobs, then decided it was time for a career change and applied for a license to sell insurance.

“I saw a fellow who was in insurance, and he had a nice property, a nice home,” Cross said.

He founded Cross Insurance and initially worked out of the family home. Nine years later, as the company continued to grow, Cross hired employees and moved the business to a downtown office. Cross Insurance completed its first acquisition of another agency in 1963 and has since acquired more than 100 agencies, growing into a regional powerhouse.

Two of Cross’ sons and two of his grandsons followed him into the business. Son Royce Cross is now the company’s president and CEO, and his late son Brent Cross served as executive vice president until his death in 2015. Grandson Jonathan Cross is now executive vice president, and grandson Woodrow “Woody” Cross works as a commercial account executive.


Royce Cross said he works closely with his father, who is as supportive and enthusiastic about the business as ever. Decisions they have made together include becoming the named sponsor of the Cross Insurance Center in Bangor and Cross Insurance Arena in Portland.

Those sponsorships are more about supporting local communities than they are about promoting the business, Royce Cross said, but they have helped make Cross Insurance a household name.

“We have no problem with name recognition, I can tell you that,” he said, an observation likely buoyed by the Cross Insurance signs that hang in TD Garden, at Gillette Stadium in Foxborough, Massachusetts, and at Fenway Park. Cross Insurance is an official insurance partner with the Red Sox, Patriots and Bruins.

On Friday, the father and son talked jovially about Woodrow Cross’ continued ambition to grow his business empire even at 100. The subject of Necco Wafers came up, a treat Woodrow Cross enjoyed as a child, and he joked that he would still like to buy the company.

“Anything he likes, he wants to buy the company,” Royce Cross said.

When asked for the secret to his longevity and how he has been able to remain so active for a century, Cross displayed his characteristic humility and matter-of-fact attitude.

“I just fell into it I guess,” he said. “I always liked my vegetables.”


Even at 100, Cross is still being recognized for his decades of effort and achievement.

In celebration of his recent birthday, the city of Bangor honored Cross with a key to the city to express its appreciation for his accomplishments and dedication to the area. The city issued a letter saying Cross is “living proof that with hard work, perseverance can really lead to positive change.”

On Jan. 27, the Bangor Region Chamber of Commerce will honor Cross with its most prestigious award, the Norbert X. Dowd Award for lifetime achievement, named after a former longtime chamber executive.

“Woodrow has long been an advocate for both business and employee development in the Bangor region and has successfully grown the insurance agency from a sole entrepreneur to a multi-office, multistate organization with over 800 employees,” the chamber said in its award notice. “Mentoring new hires of all ages, supporting professional growth and encouraging community involvement have always been his business practice. A strong work ethic, integrity, business acumen, perseverance and professionalism are but a few of the strengths we most admire in him. He is a longstanding member of his church and for decades a supporter of numerous civic and nonprofit organizations in and around Bangor.”


A recipient of many industry, community and personal accolades, Cross received an honorary Doctorate of Business Administration degree from Husson University in May 2006. He has long been an advocate for business and employee development in the Bangor region.

Chamber Chairman Lee Speronis said Cross has had numerous opportunities to relocate the insurance company to a larger metro area but chose to keep the bulk of those jobs in Maine.

“He’s kept the corporate headquarters right here in Bangor,” said Speronis, who is also director of the School of Hospitality, Sport and Tourism Management at Husson University in Bangor. “They could have easily gone to Greater Boston, but they didn’t. Mr. Cross is a gentleman of integrity and loyalty to his community.”

Cross said the secret of his success as a businessman is simple: He has always put his customers first, no matter what.

“That’s really important,” he said. “They knew they were going to be taken care of if they called, because I didn’t make any exceptions.”