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Bill Green’s Maine did a story on our Founder, Woodrow W. Cross.

Helping build the Cross Insurance Agency into what it is today, Royce Cross, President and CEO, reflects upon his ongoing successful career in the insurance business

Woodrow Cross built his business into one of New England’s largest insurers – and a partner of the Red Sox, Patriots and Bruins – while also being a major community supporter.

Agency Checklists’ article about our Founder & Chairman, Woodrow W. Cross.

With the addition of President Insurance Agency, located in Quincy, Massachusetts, Cross Insurance now has operations in more than a dozen offices throughout Massachusetts. A majority of operations exist in and around the Greater Boston region.

Cross Insurance has partnered with two boutique insurance agencies which specialize in writing personal lines insurance for high net worth individuals. Cross looks forward to growing its presence in the Connecticut marketplace with the addition of these two agencies.

Royce Cross was awarded for teaching students the financial and business skills they’ll need to succeed as adults.

For the second year in a row, Cross Insurance was included in The Largest Insurance Brokers of Massachusetts list produced by the Boston Business Journal. Cross Insurance moved up one spot from 8th place to 7th place.

On August 8th, Insurance Journal released its annual list of the Top 100 Independent Property/Casualty Agencies. Cross Insurance ranked 18th.

“Eric Jermyn is a terrific addition to the Cross Insurance team. With his extensive industry knowledge and sales experience, we expect Cross Employee Benefits to grow and prosper under his leadership,” said Jonathan Cross, Executive Vice President of Cross Insurance.

In 1923, Woodrow Cross, a 6-year-old living in the countryside of Maine, entered into the world of business. With a two-wheel wagon strapped to his pony and a bag of seed, young Woodrow took off around town selling seed to neighbors and farmers. It was at this young age that Woodrow began to develop the skills essential to becoming a businessman and his own boss.