Woodrow Cross founded his namesake agency in 1954
Perseverance. Integrity. Values. These are three of the words that come to mind for many when they think of Woodrow Cross.
Over the Christmas holidays, Woodrow Cross, the founder and current Chairman of Cross Insurance, celebrated his 100th birthday with family, friends and the many employees of Cross Insurance. With Cross Insurance’s growing presence in the Massachusetts insurance marketplace, we thought it might be interesting and inspiring to Massachusetts agents to read about Mr. Cross and his surprising career in insurance.
While a Maine insurance agent for over 60 years, Mr. Cross did not grow up in insurance. Born a century ago in Bradford Maine, his father actually owned and ran the town’s country store. As such, Mr. Cross’ first foray into the business world was actually selling seed via a two-wheel wagon strapped to his pony as a six-year old. Once a teenager, however, he joined his father in running the family’s country store.
After the sudden passing of his father during the Great Depression, Mr. Cross took over the running of the store in order to support his mother and younger siblings. He was 21.
For the next 16 years, Mr. Cross ran the store, in addition to enlisting and fighting in the Pacific during World War II, getting married in 1945, and starting a family, which ultimately included five children. In 1954, however, looking for new opportunities and better schools for his children, Mr. Cross and his wife decided to sell the family store and move to the city of Bangor.
Once ensconced in Bangor, Mr. Cross set upon finding a new career. His first jobs in his new city included working at a local mill, and in construction. Ironically, his stint in construction included working nights to ensure the cement properly settled during the construction of the Bangor Auditorium – the same auditorium that is now named as the Cross Insurance Center.
Ultimately, as fate would have it, Mr. Cross settled on an insurance career. While never having studied the subject, he had always had an interest in learning about insurance since the day, way back when, a friend had offered to sell his agency to him. Embracing his new profession, Mr. Cross studied and became licensed as a producer eventually opening the Woodrow W. Cross Agency – now known as Cross Insurance – from his kitchen table in 1954. He was 37.
Working from home over the next nine years, Mr. Cross built up his agency’s business bit-by-bit. In 1963, the Cross agency left the family home for an office in downtown Bangor. That year also saw the agency hire its first employee as well as the acquisition of its first agency. In the 1970s, Mr. Cross’ sons joined the family business working alongside their father. The agency now also counts members of the third generation of the Cross family as well.
From those humble beginnings, Mr. Cross, and his family, have grown the agency from a one-person operation in 1954, to one of the largest family-owned agencies in the country. In 2017, the agency counts more than 35 branches and upwards of 800 employees throughout New England. If that is not impressive enough, the agency has also acquired over 110 agencies over the years.
And while having just completed 100 years, Mr. Cross is still as involved as ever in the company. While his son, Royce, is the actual president of Cross Insurance and his grandson Jonathon is Executive Vice President, Woodrow Cross still comes into the office a couple of days a week to check on things. As interested as ever in insurance, he also continues to talk about insurance and his agency even on his days off.
Well-wishes from around New England
It is a fitting testament to his career in insurance, that The Cross Insurance Facebook page is filled with well-wishes to Mr. Cross attesting to the mark he has made not only in the insurance industry around New England but with the many employees who work for him.
As such, we thought independent agents everywhere would be happy in hearing about this latest milestone of Mr. Cross’ as well as to join in wishing this fellow independent agent from Maine a many happy returns.
Happy 100th birthday Mr. Cross!