Woodrow dabbled in other miniature business ventures in his childhood until he began working at his father’s country store as a teenager.  Woodrow worked with his father and learned from him, but for only a few short years.  In 1938, Woodrow’s father abruptly passed away, leaving Woodrow, at 21-years-old, in charge of running the store to support his mother and younger siblings.

Over the next 16 years, Woodrow ran the store, fought in World War II in the Pacific theater, married, and started a family.  It was in 1954 that Woodrow and his wife, Janette, decided to make some changes; Woodrow sold his store so he could spend more time with his children, and the family moved to Bangor, Maine so the children could attend better schools. 

While in Bangor, Woodrow sought out employment any way he could.  He worked at a local mill and worked nights ensuring that cement properly settled during the construction of the Bangor Auditorium – now rebuilt and named the Cross Insurance Center.  During this time, Woodrow chose to begin studying insurance, an area of work he had wanted to learn more about ever since a friend petitioned Woodrow to purchase his agency many years before.

After months of rigorous studying, Woodrow became licensed to sell Property & Casualty Insurance, Fire Insurance, and Life Insurance.  With license in hand and no office, Woodrow began the Woodrow W. Cross Agency – now known as Cross Insurance – from his kitchen table.  While working out of home, Woodrow established a network of carriers he could provide coverage through and picked up a book of business that belonged to an agency which had recently gone bankrupt.

In 1963, Woodrow moved his at-home agency to an office in downtown Bangor, hired his first employee and acquired his first agency.  Now, Cross Insurance is still headquartered in Bangor, but has more than 30 locations and more than 700 employees spread throughout New England, as a result of more than 110 acquisitions.

At the age of 98, Woodrow is still working full-time at Cross Insurance, where he remains Chairman and plays an active role in day-to-day activities.  Woodrow’s eldest son, Royce, who joined the agency in 1970, is President of the company, while Woodrow's younger son Brent, who joined in 1980, and grandson Jonathan, who joined in 1996, reside as Executive Vice Presidents.