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.


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

Risk Focus: Cyber

Expanding Cyber BI

Cyber business interruption insurance is a thriving market, but growth carries the threat of a mega-loss. 
By: | March 5, 2018 • 7 min read

Lingering hopes that large-scale cyber attack might be a once-in-a-lifetime event were dashed last year. The four-day WannaCry ransomware strike in May across 150 countries targeted more than 300,000 computers running Microsoft Windows. A month later, NotPetya hit multinationals ranging from Danish shipping firm Maersk to pharmaceutical giant Merck.


Maersk’s chairman, Jim Hagemann Snabe, revealed at this year’s Davos summit that NotPetya shut down most of the group’s network. While it was replacing 45,000 PCs and 4,000 servers, freight transactions had to be completed manually. The combined cost of business interruption and rebuilding the system was up to $300 million.

Merck’s CFO Robert Davis told investors that its NotPetya bill included $135 million in lost sales plus $175 million in additional costs. Fellow victims FedEx and French construction group Saint Gobain reported similar financial hits from lost business and clean-up costs.

The fast-expanding world of cryptocurrencies is also increasingly targeted. Echoes of the 2014 hack that triggered the collapse of Bitcoin exchange Mt. Gox emerged this January when Japanese cryptocurrency exchange Coincheck pledged to repay customers $500 million stolen by hackers in a cyber heist.

The size and scope of last summer’s attacks accelerated discussions on both sides of the Atlantic, between risk managers and brokers seeking more comprehensive cyber business interruption insurance products.

It also recently persuaded Pool Re, the UK’s terrorism reinsurance pool set up 25 years ago after bomb attacks in London’s financial quarter, to announce that from April its cover will extend to include material damage and direct BI resulting from acts of terrorism using a cyber trigger.

“The threat from a cyber attack is evident, and businesses have become increasingly concerned about the extensive repercussions these types of attacks could have on them,” said Pool Re’s chief, Julian Enoizi. “This was a clear gap in our coverage which left businesses potentially exposed.”

Shifting Focus

Development of cyber BI insurance to date reveals something of a transatlantic divide, said Hans Allnutt, head of cyber and data risk at international law firm DAC Beachcroft. The first U.S. mainstream cyber insurance products were a response to California’s data security and breach notification legislation in 2003.

Jimaan Sané, technology underwriter, Beazley

Of more recent vintage, Europe’s first cyber policies’ wordings initially reflected U.S. wordings, with the focus on data breaches. “So underwriters had to innovate and push hard on other areas of cyber cover, particularly BI and cyber crimes such as ransomware demands and distributed denial of service attacks,” said Allnut.

“Europe now has regulation coming up this May in the form of the General Data Protection Regulation across the EU, so the focus has essentially come full circle.”

Cyber insurance policies also provide a degree of cover for BI resulting from one of three main triggers, said Jimaan Sané, technology underwriter for specialist insurer Beazley. “First is the malicious-type trigger, where the system goes down or an outage results directly from a hack.

“Second is any incident involving negligence — the so-called ‘fat finger’ — where human or operational error causes a loss or there has been failure to upgrade or maintain the system. Third is any broader unplanned outage that hits either the company or anyone on which it relies, such as a service provider.”

The importance of cyber BI covering negligent acts in addition to phishing and social engineering attacks was underlined by last May’s IT meltdown suffered by airline BA.

This was triggered by a technician who switched off and then reconnected the power supply to BA’s data center, physically damaging servers and distribution panels.

Compensating delayed passengers cost the company around $80 million, although the bill fell short of the $461 million operational error loss suffered by Knight Capital in 2012, which pushed it close to bankruptcy and decimated its share price.

Mistaken Assumption

Awareness of potentially huge BI losses resulting from cyber attack was heightened by well-publicized hacks suffered by retailers such as Target and Home Depot in late 2013 and 2014, said Matt Kletzli, SVP and head of management liability at Victor O. Schinnerer & Company.


However, the incidents didn’t initially alarm smaller, less high-profile businesses, which assumed they wouldn’t be similarly targeted.

“But perpetrators employing bots and ransomware set out to expose any firms with weaknesses in their system,” he added.

“Suddenly, smaller firms found that even when they weren’t themselves targeted, many of those around them had fallen victim to attacks. Awareness started to lift, as the focus moved from large, headline-grabbing attacks to more everyday incidents.”

Publications such as the Director’s Handbook of Cyber-Risk Oversight, issued by the National Association of Corporate Directors and the Internet Security Alliance fixed the issue firmly on boardroom agendas.

“What’s possibly of greater concern is the sheer number of different businesses that can be affected by a single cyber attack and the cost of getting them up and running again quickly.” — Jimaan Sané, technology underwriter, Beazley

Reformed ex-hackers were recruited to offer board members their insights into the most vulnerable points across the company’s systems — in much the same way as forger-turned-security-expert Frank Abagnale Jr., subject of the Spielberg biopic “Catch Me If You Can.”

There also has been an increasing focus on systemic risk related to cyber attacks. Allnutt cites “Business Blackout,” a July 2015 study by Lloyd’s of London and the Cambridge University’s Centre for Risk Studies.

This detailed analysis of what could result from a major cyber attack on America’s power grid predicted a cost to the U.S. economy of hundreds of billions and claims to the insurance industry totalling upwards of $21.4 billion.

Lloyd’s described the scenario as both “technologically possible” and “improbable.” Three years on, however, it appears less fanciful.

In January, the head of the UK’s National Cyber Security Centre, Ciaran Martin, said the UK had been fortunate in so far averting a ‘category one’ attack. A C1 would shut down the financial services sector on which the country relies heavily and other vital infrastructure. It was a case of “when, not if” such an assault would be launched, he warned.

AI: Friend or Foe?

Despite daunting potential financial losses, pioneers of cyber BI insurance such as Beazley, Zurich, AIG and Chubb now see new competitors in the market. Capacity is growing steadily, said Allnutt.

“Not only is cyber insurance a new product, it also offers a new source of premium revenue so there is considerable appetite for taking it on,” he added. “However, whilst most insurers are comfortable with the liability aspects of cyber risk; not all insurers are covering loss of income.”

Matt Kletzli, SVP and head of management liability, Victor O. Schinnerer & Company

Kletzli added that available products include several well-written, broad cyber coverages that take into account all types of potential cyber attack and don’t attempt to limit cover by applying a narrow definition of BI loss.

“It’s a rapidly-evolving coverage — and needs to be — in order to keep up with changing circumstances,” he said.

The good news, according to a Fitch report, is that the cyber loss ratio has been reduced to 45 percent as more companies buy cover and the market continues to expand, bringing down the size of the average loss.

“The bad news is that at cyber events, talk is regularly turning to ‘what will be the Hurricane Katrina-type event’ for the cyber market?” said Kletzli.

“What’s worse is that with hurricane losses, underwriters know which regions are most at risk, whereas cyber is a global risk and insurers potentially face huge aggregation.”


Nor is the advent of robotics and artificial intelligence (AI) necessarily cause for optimism. As Allnutt noted, while AI can potentially be used to decode malware, by the same token sophisticated criminals can employ it to develop new malware and escalate the ‘computer versus computer’ battle.

“The trend towards greater automation of business means that we can expect more incidents involving loss of income,” said Sané. “What’s possibly of greater concern is the sheer number of different businesses that can be affected by a single cyber attack and the cost of getting them up and running again quickly.

“We’re likely to see a growing number of attacks where the aim is to cause disruption, rather than demand a ransom.

“The paradox of cyber BI is that the more sophisticated your organization and the more it embraces automation, the bigger the potential impact when an outage does occur. Those old-fashioned businesses still reliant on traditional processes generally aren’t affected as much and incur smaller losses.” &

Graham Buck is editor of He can be reached at