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

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In the Fast-Paced World of Retail, This Risk Manager Strives to Mitigate Risks Proactively and Keep Senior Leaders Informed

Janine Kral works to identify and mitigate risks, building strong partnerships with leaders and ensuring they see her as support rather than a blocker. 
By: | October 29, 2018 • 4 min read

R&I: What was your first job?

My very first paid job was working on my uncle’s ranch in British Columbia in the summers. He had cattle, horses and grapes — an unusual combo. But my first real job out of college was as a multi-line claims adjuster at Liberty Mutual.

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

Right out of college I applied for a job that turned out to be a claims adjuster at Liberty Mutual. I accepted because they were offering six weeks of training in Southern California, and at the time that sounded really fun. I spent about three years at Liberty Mutual and then I spent a short period of time at a smaller regional insurance company that hired me to start a workers’ compensation claims administration program.

I was hired at Nordstrom as the Washington Region Risk Manager, which was my first job in risk management. When I started at Nordstrom, the risk management department had about five people, and over the years it has grown to about 75. I’ve been vice president for 11 years.

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

I would say that technology has probably been the biggest change. When I started many years ago, it was all paper and no RMIS.

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R&I: What risks does the retail industry face that are unique?

We deal with a lot of people — employees and customers. With physical brick and mortar settings, there are the unique exposures with people moving in and out in a public environment. And of course, with ecommerce, we have a lot of customer and employee data, which creates cyber risk — which is not necessarily a unique risk in today’s environment.

R&I: Can you describe your approach to working with senior leaders and front-line staff alike to further risk management initiatives?

It starts with keeping the pulse of what’s happening with the business. Retail moves really fast. In order to identify and mitigate risks proactively, we identify top risk areas and topics, and then we ensure that we have strong partnerships with the leaders responsible for those areas. Trust is critical, ensuring that leaders see us as a support rather than a blocker.

R&I: What role does technology play in your company’s approach to risk management?

Janine Kral, claims adjuster, Nordstrom

We have an internal risk management information system that all of our locations report events into — every type of incident is reported, whether insured or uninsured. Most of these events are managed internally by risk management, and our guidelines require that prevention be analyzed on each one. Having all event data in one system allows us to use the data for trending and also helps us better predict what may happen in the future, and who we need to work with to mitigate risks.

R&I: What advice might you give to students or other aspiring risk managers?

My son is a sophomore in college, and I tell him and his friends all the time not to rule out insurance as a career opportunity. My advice is to cast a wide net and do your homework. Research all the different types of opportunities. Read a lot — articles, industry magazines, LinkedIn. Be proactive and reach out to people you find interesting and ask them about their careers. Don’t be shy and wait for people and opportunities to come to you. Ask questions. Build networks. Be curious and keep an open mind.

R&I: What are your goals for the next five to 10 years of your career?

I have always been passionate about continuous improvement. I want to continue to find ways to add value to my company and to this industry.

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

My favorite book is Shantaram by Gregory David Roberts. It’s a true story about a man who was in prison in Australia after being convicted of armed robbery, and he escaped to India. While in India, he passed himself off as a doctor in a slum. It’s a really interesting story, because this is a convicted criminal who ends up helping others. I am not always successful in getting others to read the book because it’s 1,000 pages and definitely a commitment.

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

Fiorella’s in Newton, Massachusetts. Great Italian food and a great overall experience.

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R&I: What is your favorite drink?

“Sister Carol.” I have no idea what is in it, and I can only get it at a local bar in Seattle. It’s green but it’s delicious.

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

Skydiving. Not tandem and without any sort of communication from the ground. Scary standing on a wing of a plane, but very peaceful once the chute opened, slowly floating down by myself.

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

I can’t think of one individual person. For me, the real heroes are people who have a positive attitude in the face of adversity. People who are resilient no matter what life brings them.

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

It’s rewarding to help solve problems and help people. I am proud of the support that my team provides others. &




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