Sixty-three years ago, Woodrow Cross founded Bangor, Maine-based Cross Insurance and after celebrating his 100th birthday on Dec. 29, 2016, he is still actively involved in the company.

The father of five, grandfather of 14 and great-grandfather of 13 continues to oversee Cross Insurance, still makes frequent trips to the office and works closely with his son, Royce, now CEO. Additionally, Woodrow Cross remains a licensed insurance agent with big plans to grow the business — because “there is a lot more business left to do,” he says.

Woodrow Cross celebrates his 100th birthday recently.
Woodrow Cross celebrates his 100th birthday recently.

At six years old, he sold seeds door to door. By the time he turned 10, he had ventured into chicken farming and learned to leverage his business’s potential. He began taking out loans to purchase baby chicks, which he sold at a profit when they matured, allowing him to repay his creditors and continue to grow his enterprise. In his teens, he transitioned to working in his father’s general store.

In the midst of the Great Depression, Woodrow’s father died. Twenty-one-year-old Woodrow assumed responsibility for running the business and caring for the Cross family. It was a personal challenge for him to keep the business vital during difficult economic times and it made an impact on the young man that would last a lifetime.

When the United States entered into World War II, Cross enlisted in the Army, serving as a staff sergeant in the Pacific theater, including campaigns in New Guinea and the Philippines, as well as occupation duty in Japan.

Upon his discharge, Cross relocated his family to Bangor. While working at various construction jobs to support his family, he decided it was time for a career change. He obtained his license to sell insurance.

Cross sold his first insurance policy for $7 with a commission of $1.50. Nine years later, as the company continued to grow and he hired employees, he moved the business to a downtown office space. He acquired his first agency in 1963. Since then, Cross insurance has acquired more than 100 agencies.

Over the years, two of his sons and two of his grandsons have followed him into the business. Royce serves as company President and CEO, and his late son Brent served as executive vice president. Grandson Jonathan serves as executive vice president and grandson Woodrow II works as a commercial lines account executive.

pictured L-R: Jonathan Cross (grandson); Royce Cross (son); the late Brent Cross (son); Woodrow Cross; and grandson Woodrow Cross.
pictured L-R: Jonathan Cross (grandson); Royce Cross (son); the late Brent Cross (son); Woodrow Cross; and grandson Woodrow Cross.

EBA spoke with Cross about his career that has spanned the election of 18 U.S. presidents, the invention of the computer and the World Wide Web. This is an edited version of the discussion.

EBA: What is the biggest lesson you’ve learned?

Cross: Health insurance … is one of the most sacred products we sell. To be blunt, if we don’t have our health, little else matters. We need to demonstrate to people we care.

EBA: What is your outlook on the future of the employee benefits space? The independent brokerage model?

Cross: People will always recognize they need an independent broker to guide them through the maze of what insurance companies offer what for products. Recently, our role has evolved to guidance on complying with government regulations. So today when we make a presentation it leans more to a compliance discussion as opposed to about our insurance products.

EBA: What is the greatest advice you can offer to those thinking of joining or starting an employee benefit brokerage?

Cross: Without question, become a student of governmental compliance laws. Second thing: Care. Help businesses understand what they need to do to comply with the laws. They want to obey the law — show them how. Also, the healthcare of the employees and their families gets about as personal as it gets. Third thing: Do your best to make all of this affordable.

EBA: What motivates you to work at 100 years old?

Cross: The thrill of the game. It’s been exciting and fun to work with my family and others. It’s been rewarding to provide a product to help so many. It’s been incredibly rewarding to watch the business. I’ve enjoyed it and still enjoy it and have no plans to leave the business.

EBA: How has regulation of the employee benefits/401(k) space changed?

Cross: I almost don’t know where to stop on this one. Living to 100, I can remember no or at the very most little regulation to an industry now that is heavily regulated.

EBA: After so many years in the industry, would you do it all again?

Cross: I’ve enjoyed my life and said it many times, I would be happy to start all over and live my life again. Of course a few things I’d change, but it’s been great.

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