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Brokers

Decades Spent Serving Clients

With a lifetime of accomplishments under his belt, Woodrow Cross wants to keep going.
By: | January 17, 2017 • 4 min read
Topics: Brokerage

At the age of 100, Woodrow Cross has no plans to retire.

The founder and chairman an of Cross Insurance – the Bangor, Maine-based independent insurance provider that employs 800 people at 40 locations in five states – still goes to work a few days per week to schmooze with his staff, service his insurance clients and grow the business.

He won’t retire, Cross said, because running his insurance dynasty is more fun than anything else.

“I like the challenge,” he said. “I like growing the business. I like the people.”

A Sociable Man

Cross has made a few concessions to age, such as moving to an assisted living facility, employing a driver and using a wheelchair. His hearing isn’t what it used to be. When he walks, or rolls, into his office, he makes the rounds of hellos and well wishes from the staff, which include his son Royce, president and CEO; grandson Jonathan, executive vice president; and grandson Woodrow, commercial lines account executive. His late son Brent served as executive vice president.

The Cross family, from left, Jonathan Cross (grandson); Royce Cross (son); the late Brent Cross (son); Woodrow Cross; and grandson Woodrow Cross. Photo taken in 2014.

“It’s exhilarating,” he said to see his family thriving and contributing. It makes his heart swell with pride and joy.

He is a sociable man. When Cross was proprietor of a country store in the tiny hamlet of Bradford, Maine, during the Depression, the store’s wood stove served as the town’s meeting spot.

There was no television and few radios, said his son Royce. No alcohol because of Prohibition, although a few men occasionally bought large quantities of vanilla extract, putatively to bake a cake.

“The entertainment was visiting with each other in the store,” Royce Cross said, “and Woodrow was at the center.”

His personality continues to bring in business. At a recent event recognizing his business and civic accomplishments, Woodrow Cross and another honoree made their acquaintance – in whispers – at the rear of the stage as a speaker delivered his speech at the podium.

“They really hit it off,” Royce Cross said.

The new acquaintance, it turned out, was part of a large national organization, and he was so impressed that he moved the company’s sizable insurance accounts to Cross Insurance.

“Sales is what I love,” Woodrow Cross said. “I haven’t lost the excitement. I hope I’m improving.”

Servicing Clients

Cross also takes pleasure in doing right by his clients, Royce said. For example, when a client’s property burned one Christmas Eve after the office had closed early for the holiday, Cross took Royce to the property to work on the claim, delaying their own festivities.

“That was a good Christmas. When you help someone, that’s rewarding,” Royce said.

“We were brought up to help,” he said.

Without resorting to intimidation, despotism or tyranny, Cross is a perfectionist when it comes to service, Royce said. “He taught us, ‘There’s a limited amount you can do for your clients on pricing, so come back on service.’ ”

Woodrow Cross in a University of Maine Hockey jersey.

When banks and real estate agencies need binders for closing, Cross taught his sons to “move quickly. Close the deal before they can go to the competition,” Royce said.

Woodrow Cross built the largest independent insurance provider in the Northeast, acquired more than 100 agencies, has buildings in Bangor and Portland bearing his name, was awarded an honorary doctorate and is generally considered a bastion of Bangor’s economy.

But it’s also important to him that he remembers his first business of selling seed door to door at age 6, and his teenage entrepreneurial venture of raising baby chickens and selling them at a profit.

“He doesn’t see himself as a big important guy, and he doesn’t permit grandiosity in his children,” Royce said. “I speak to him every day of my life, and I can’t recall a conversation when we talked about ourselves as pretty special. He wouldn’t like it.”

The combination of ambition for future accomplishments and modesty about past ones is the mainspring behind the company’s growth.

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The company that Cross started in 1954 at his kitchen table now sells and services personal and commercial insurance lines, employee benefits, surety bonds, comprehensive risk management advice and counsel, and specialized products focused on higher education and high net worth needs.

Cross’ extroversion, ambition, love of family and community, resourcefulness and honesty is a perfect fit for his profession, said Royce, who joined the company in the 1970s.

Indeed, Woodrow Cross said, no pleasure associated with retirement would deliver the shot of joy, pride and adrenaline that he gets from his work.

Does he have any regrets for trips not taken or golf not played?

“No regrets,” Cross said. “No bucket list.” &

Susannah Levine writes about health care, education and technology. She can be reached at [email protected]

More from Risk & Insurance

More from Risk & Insurance

The Profession

Curt Gross

This director of risk management sees cyber, IP and reputation risks as evolving threats, but more formal education may make emerging risk professionals better prepared.
By: | June 1, 2018 • 4 min read

R&I: What was your first job?

My first non-professional job was working at Burger King in high school. I learned some valuable life lessons there.

R&I: How did you come to work in risk management?

After taking some accounting classes in high school, I originally thought I wanted to be an accountant. After working on a few Widgets Inc. projects in college, I figured out that wasn’t what I really wanted to do. Risk management found me. The rest is history. Looking back, I am pleased with how things worked out.

R&I: What is the risk management community doing right?

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I think we do a nice job on post graduate education. I think the ARM and CPCU designations give credibility to the profession. Plus, formal college risk management degrees are becoming more popular these days. I know The University of Akron just launched a new risk management bachelor’s program in the fall of 2017 within the business school.

R&I: What could the risk management community be doing a better job of?

I think we could do a better job with streamlining certificates of insurance or, better yet, evaluating if they are even necessary. It just seems to me that there is a significant amount of time and expense around generating certificates. There has to be a more efficient way.

R&I: What was the best location and year for the RIMS conference and why?

Selfishly, I prefer a destination with a direct flight when possible. RIMS does a nice job of selecting various locations throughout the country. It is a big job to successfully pull off a conference of that size.

Curt Gross, Director of Risk Management, Parker Hannifin Corp.

R&I: What’s been the biggest change in the risk management and insurance industry since you’ve been in it?

Definitely the change in nontraditional property & casualty exposures such as intellectual property and reputational risk. Those exposures existed way back when but in different ways. As computer networks become more and more connected and news travels at a more rapid pace, it just amplifies these types of exposures. Sometimes we have to think like the perpetrator, which can be difficult to do.

R&I: What emerging commercial risk most concerns you?

I hate to sound cliché — it’s quite the buzz these days — but I would have to say cyber. It’s such a complex risk involving nontraditional players and motives. Definitely a challenging exposure to get your arms around. Unfortunately, I don’t think we’ll really know the true exposure until there is more claim development.

R&I: What insurance carrier do you have the highest opinion of?

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Our captive insurance company. I’ve been fortunate to work for several companies with a captive, each one with a different operating objective. I view a captive as an essential tool for a successful risk management program.

R&I: Who is your mentor and why?

I can’t point to just one. I have and continue to be lucky to work for really good managers throughout my career. Each one has taken the time and interest to develop me as a professional. I certainly haven’t arrived yet and welcome feedback to continue to try to be the best I can be every day.

R&I: What have you accomplished that you are proudest of?

I would like to think I have and continue to bring meaningful value to my company. However, I would have to say my family is my proudest accomplishment.

R&I: What is your favorite book or movie?

Favorite movie is definitely “Good Will Hunting.”

R&I: What’s the best restaurant you’ve ever eaten at?

Tough question to narrow down. If my wife ran a restaurant, it would be hers. We try to have dinner as a family as much as possible. If I had to pick one restaurant though, I would say Fire Food & Drink in Cleveland, Ohio. Chef Katz is a culinary genius.

R&I: What is the most unusual/interesting place you have ever visited?

The Grand Canyon. It is just so vast. A close second is Stonehenge.

R&I: What is the riskiest activity you ever engaged in?

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A few, actually. Up until a few years ago, I owned a sport bike (motorcycle). Of course, I wore the proper gear, took a safety course and read a motorcycle safety book. Also, I have taken a few laps in a NASCAR [race car] around Daytona International Speedway at 180 mph. Most recently, trying to ride my daughter’s skateboard.

R&I: If the world has a modern hero, who is it and why?

The Dalai Lama. A world full of compassion, tolerance and patience and free of discrimination, racism and violence, while perhaps idealistic, sounds like a wonderful place to me.

R&I: What about this work do you find the most fulfilling or rewarding?

I really enjoy the company I work for and my role, because I get the opportunity to work with various functions. For example, while mostly finance, I get to interact with legal, human resources, employee health and safety, to name a few.

R&I: What do your friends and family think you do?

I asked my son. He said, “Risk management and insurance.” (He’s had the benefit of bring-your-kid-to-work day.)

Katie Dwyer is an associate editor at Risk & Insurance®. She can be reached at [email protected]