Our Founder, Woodrow Cross

The legacy of our late founder, Woodrow Cross, continues to be written. His legendary work ethic and inspiring entrepreneurism continue to be a tradition three generations later.


Even at a young age, Woodrow’s work ethic was evident. Raised in the small town of Bradford, Maine, Woodrow began selling seed to neighbors at the young age of six. Later he would raise chickens and sell those.  


In his teen years, Woodrow began working at his father’s store. His father passed away abruptly, leaving 21-year-old Woodrow in charge of running the store to support his mother and younger siblings.


Woodrow served in the Army during WWII in the Pacific Theatre. During the war he married his sweetheart, Janette Bean, and they would raise five children together.   


Woodrow sold his store to spend more time with his children. The family moved to Bangor, Maine. Woodrow worked a number of jobs while beginning to study insurance. Once he became licensed, he founded the Woodrow W. Cross Agency from his kitchen table.


The at-home agency finally moved to an office in downtown Bangor. Woodrow hired his first employee, and even acquired another agency.

“Woodrow Cross’s life exemplified the American dream in every way. He created an insurance empire from scratch and managed to do it with dignity and integrity.”

The Second Generation


Royce and Brent Cross, Woodrow’s sons, join the family agency.


Royce Cross was appointed President of Cross Insurance. The company completed nine acquisitions.


Cross Insurance expands into New Hampshire.


The agency continues to grow, moving into Massachusetts.


The Kraft Sports Group, including the New England Patriots, become a client.


The Cross Insurance Center opens, the company’s first naming partnership. Woodrow Cross, who had a hand constructing the original auditorium before the new one was built, is given the honor of being the first to take a seat in the new event center.


Brent Cross, Executive Vice President, passed away after a courageous battle with cancer. Brent saw the company grow from five employees to over 700, and was key to facilitating partnerships with the New England Patriots, Boston Red Sox, and the Boston Bruins.



Cross announces expansion into Connecticut, partnering with an agency in Fairfield County.

The Legacy Continues


Cross acquires its first agency in New York. 


Woodrow Cross passed away at the age of 103.


Jonathan Cross, Woodrow’s grandson, was named President and CEO of the company. Royce Cross continues to serve as Chairman.