Risk Scenario

Midnight Blitz

On Cyber Monday, skilled hackers diminish an online retailer's credibility in mere minutes.
By: | November 13, 2014 • 8 min read
Risk Scenarios are created by Risk & Insurance editors along with leading industry partners. The hypothetical, yet realistic stories, showcase emerging risks that can result in significant losses if not properly addressed.

Disclaimer: The events depicted in this scenario are fictitious. Any similarity to any corporation or person, living or dead, is merely coincidental.

The Citadel

The October 2015 cover of the trade publication Retailer’s World featured a picture of Paul Vitez, general counsel for cloud host Va-Voom!, which rewrote the book on online shopping, making a billionaire of its founder, Teddy Houck.

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In glowing prose, the author of the Retailer’s World cover story related Vitez’ impressive academic record at Haverford College, his background in finance and his role in earning for Va-Voom! the nickname of “The Citadel” for its innovative, committed approach to cyber security.

Employing the “prison, not a castle” approach to cyber security, Vitez and Va-Voom! created “honey- pots” within the Va-Voom! system, decoys which looked like they contained important data but were not actually part of the internal network.

Moving much more swiftly than its competitors, Va-Voom! also spent millions to implement chip and pin credit card technology on its credit cards, a much more secure way to store sensitive financial and personal information than the traditional magnetic strip.

Again with an eye toward short-term investment in operations and a goal of long-term success, Vitez was given carte blanche by Teddy Houck and the Va-Voom! board of directors to spend top dollar for information technology talent that had honed their skills in the high-stakes environments of the CIA and the Department of Defense.

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From an information technology policy perspective, Va-Voom! was a demanding place to work. Under Vitez’ direction, the use of data encryption was heavily enforced. It also had a strict company policy barring employees from connecting personal devices to any computer equipment owned by Va-Voom! or to its network.

In 2014 and 2015, one by one, major retailers — even banking institutions — were hit by cyber attacks that undermined the public’s faith in those companies, doing serious mid- to long-term damage to their reputations. Retailers that learned only too well the degree to which they were vulnerable to attack found in Va-Voom! a business partner they felt they could trust.

Rather than being dampened by cyber fears, the trend of cyber attacks in 2014 and early 2015 actually increased the number of retailers that wanted to do business with Va-Voom!

The company’s insurance program was something of an anomaly, considering its position in the industry. Starting with a substantial retention, Va-Voom! carried property and professional liability coverage for its employees.

The company considered but never purchased coverage that would substantially indemnify the hundreds of retailers and other service providers that used its services, were Va-Voom! to be the victim of a cyber-security incident. It carried third-party liability insurance, but not as much as you would think a company of its size would carry.

“Really?” Vitez memorably said during a meeting with Steve Francis, the company’s chief risk officer and company CFO Maribel Kelly, when the subject of cyber security indemnification was broached by Va-Voom!’s broker, himself no slouch when it came to these matters.

With an eye to the merciless whims of stock market investors, Vitez and Kelly sided against Steve Francis when he argued that the cost of the premium, though it would put a slight dent in the company’s bottom line on a quarterly basis, was well worth the expense.

“Nobody manages this risk better than we do,” Vitez said, crossing his arms across his chest.

“We can and do own this risk,” he said.

Steve Francis looked at Vitez across the table but didn’t say what he was thinking. What he was thinking was, “You just bit off way more than you can chew, Mr. Haverford.”

The Blitz

Just before midnight on Nov. 30, 2015, the Monday after Thanksgiving, known in retailing as Cyber Monday, a highly sophisticated and well-coordinated cyber-attack began, erasing Va-Voom!’s considerable credibility in a matter of minutes.

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Here’s how it unfolded.

At five minutes to midnight, the websites of 10 of the largest retailers that sold on the Va-Voom! site went down. The retailers were so in the dark about what had happened to them that it took hours to put together that the source of the attack was coming from within Va-Voom!’s vaunted information technology system.

Precisely at midnight, unidentified hackers used the stolen e-mail addresses of the 10 retailers’ customers to send Trojan Horses to the personal computers of millions of online shoppers.

The customers didn’t need to click on the e-mails or download attachments to empower the Trojan Horses. After a mere half hour in their inboxes, the e-mails activated a cyber-locking mechanism that shut the users out of their own computers. The only visible content on their screen was the logo of the retailer whose customer information was stolen.

Angry consumers, shut out of their personal computers, pick up their handheld devices to vent their frustration in instant messages and Tweets aimed at the retailers whose logos were frozen on their now-useless computer screens.




Several of the affected companies went public within hours with their conviction that the Trojan Horses that caused so much havoc emanated from the Va-Voom! network.

“Are you seeing this?” said David Cohen, the equally miffed general counsel for one of the retailers, on a phone call with his law school buddy Paul Vitez, as they tried to sort out the hell that had broken loose.

“Yes I’m seeing it,” said Vitez.

Vitez, normally a man of action, but temporarily flummoxed, became as passive as any teenager with a handheld device in their hand as he sat, scrolling through the Tweets and Facebook posts that were savaging the retailers and Va-Voom!

“What are you doing?” Cohen said impatiently when Vitez fell silent.

“Are you playing with your iPhone? We have a serious situation here, Paul!” Cohen said.

“I’m not playing with my iPhone!” Vitez shouted back before putting down his mobile device and trying to regain control of his emotions.

“I know we have a problem David, I know we do,” Vitez said.

But all Vitez could do beyond that was run his hands through his hair, temporarily at a loss as to exactly what to do next.

On the afternoon of December 1, the New York Times published an online story, featuring quotes attributed to Wall Street analysts from the technology and retail sectors, estimating that damage to home computers and lost online retail sales from the coordinated and ongoing cyber attack could potentially exceed $1 billion.

Black Monday and Beyond

In the aftermath of what history and newspaper editors and writers would record as “Black Monday,” Vitez and the rest of the Va-Voom! team tried to take stock of their losses and rally themselves into a recovery. They had a very hard and very expensive road ahead of them.

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Paul Vitez had used the millions accorded to him to create Va-Voom’s “prison, not a castle” approach to cyber defense and he had employed that money in an admirable and innovative fashion.

But it was in a meeting with chief risk officer Steve Francis, CFO Marabel Kelly and Va-Voom!’s technology and general liability broker Brandon Fikes that Paul Vitez came to a better, albeit painful understanding about the best allocation of capital in the quest to manage risk.

The most immediate pain that Va-Voom! was feeling were notices from five attorneys general that investigations into the Black Monday breach were underway.

‘Well, the good news is that your regulatory defense is covered, as is your first party business interruption,” Fikes said.

“Great,” Vitez said. “What else?”

Steve Francis glanced at Vitez out of one corner of his eye. He felt the pain of the losses to the company as badly as anyone, but he couldn’t help but take a bit of perverse pleasure in the discomfort of Vitez, whose arrogance, in Francis’ estimation, was going to have significant consequences, consequences that could be measured in millions of dollars.

“The rest is somewhat of a mixed bag, unfortunately,” Fikes said.

“Go on,” said Vitez who shot Francis a quick sharp look, causing Francis to turn away quickly, lest his inner thoughts become outwardly visible.

“You had some third party liability coverage, but I don’t think it’s going to be enough to cover the losses of your business partners, not to mention the shoppers whose personal computers were damaged by this event,” Fikes said.

“How much …” Vitez managed to get out before Steve Francis stepped in.

“We could have multiples of millions in exposure here, Paul,” Francis said.

Vitez shot Francis another look but Francis diplomatically kept his mouth shut.

“I don’t think we’re ever going to get to the bottom of where this attack came from and who launched it,” said the CFO, Marabel Kelly.

“What’s your advice, Brandon, about spending money on forensics?” she asked.

“I think you spend it for a couple of reasons,” Fikes said.

“One, the cost is covered by insurance. But that’s not the best reason. The best reason is that you can use forensics to learn from the event and hopefully prevent anything else as bad as this going forward,” he said.

“All right,” Kelly said. “What else?”

“There’s reputation,” Steve Francis offered.

“Some say you can put a price on it, some say you can’t,” said Fikes.

“But one thing is for sure,” he said. “You had no coverage in place for that in any event.”

There was a pause, as the significance of that statement sunk in. In the extended, painfully awkward silence, Marabel Kelly shuffled the paperwork in front of her and shifted in her seat, visibly perturbed.

Within two weeks of that difficult conversation, the pain intensified for Paul Vitez and Va-Voom! Class action lawsuits were filed on behalf of the millions of home-computer owners who alleged pain and suffering in connection with the hassle of credit card replacement and property loss from their now-useless computers.

The 10 retailers affected, now known colloquially and to their ongoing irritation as the Black Monday Ten, also filed suit.

With Va-Voom!’s uninsured losses building from the millions to the tens of millions, Paul Vitez, once a magazine cover boy, resigned his position.

Bar-Lessons-Learned---Partner's-Content-V1b

Risk & Insurance® partnered with XL Group to produce this scenario. Below are XL Group’s recommendations on how to prevent the losses presented in the scenario. These “Lessons Learned” are not the editorial opinion of Risk & Insurance®.

1. Have a crisis management response plan in place – The consequences of a cyber-attack are too expensive and too damaging for companies not to have a clear idea how they are going to respond in the event their services, or the services of their business partners are interrupted.

2. Understand your risk profile – Different companies have different cyber-risk profiles depending on their industry. Understanding your cyber-risk profile and working in conjunction with an agent and underwriter to map out the best coverage is a crucial step in avoiding being underinsured or paying too much for coverage you don’t need.

3. You are next – The realm of cyber-security and cyber-attacks is one area where an “it can’t happen here” mentality could be catastrophic. The chilling fact of the matter is that the most well-financed companies with the most sophisticated cyber defenses are vulnerable.

4. Get help – Whether it be through your insurance coverage or some other funding mechanism, find and connect with the consultants you need to help you understand the threat and how you can protect yourself. This risk environment is changing day by day and no one can afford to be content with the status quo.

5. Enforce your IT policies – Having sensible IT policies in place to minimize the potential for an attack is not enough. Companies must be proactive in seeing that employees take seriously company rules and standards on data encryption, and the use of personal devices in the workplace or in connection with company networks.

Additional Partner Resources

XL Group Cyber Product Sheet

John Coletti, Underwriting Manager of Cyber Liability, discusses cyber coverage options.




Dan Reynolds is editor-in-chief of Risk & Insurance. He can be reached at dreynolds@lrp.com.

More from Risk & Insurance

More from Risk & Insurance

High Net Worth

High Net Worth Clients Live in CAT Zones. Here’s What Their Resiliency Plan Should Include

Having a resiliency plan and practicing it can make all the difference in a disaster.
By: | September 14, 2018 • 7 min read

Packed with state-of-the-art electronics, priceless collections and high-end furnishings, and situated in scenic, often remote locations, the dwellings of high net worth individuals and families pose particular challenges when it comes to disaster resiliency. But help is on the way.

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Armed with loss data, innovative new programs, technological advances, and a growing army of niche service-providers aimed at addressing an astonishingly diverse set of risks, insurers are increasingly determined to not just insure against their high net worth clients’ losses, but to prevent them.

Insurers have long been proactive in risk mitigation, but increasingly, after the recent surge in wildfire and storm losses, insureds are now, too.

“Before, insurance was considered the only step in risk management. Now, our client families realize it is one of the many imperative steps in an effective risk management strategy,” said Laura Sherman, founding partner at Baldwin Krystyn Sherman Partners.

And especially in the high net worth space, preventing that loss is vastly preferable to a payout, for insurers and insureds alike.

“If insurers can preserve even one house that’s 10 or 20 or 40 million dollars … whatever they have spent in a year is money well spent. Plus they’ve saved this important asset for the client,” said Bruce Gendelman, chairman and founder Bruce Gendelman Insurance Services.

High Net Worth Vulnerabilities

Laura Sherman, founding partner, Baldwin Krystyn Sherman Partners

As the number and size of luxury homes built in vulnerable areas has increased, so has the frequency and magnitude of extreme weather events, including hurricanes, harsh cold and winter storms, and wildfires.

“There is a growing desire to inhabit this riskier terrain,” said Jason Metzger, SVP Risk Management, PURE group of insurance companies. “In the western states alone, a little over a million homes are highly vulnerable to wildfires because of their proximity to forests that are fuller of fuel than they have been in years past.”

Such homes are often filled with expensive artwork and collections, from fine wine to rare books to couture to automobiles, each presenting unique challenges. The homes themselves present other vulnerabilities.

“Larger, more sophisticated homes are bristling with more technology than ever,” said Stephen Poux, SVP and head of Risk Management Services and Loss Prevention for AIG’s Private Client Group.

“A lightning strike can trash every electronic in the home.”

Niche Service Providers

A variety of niche service providers are stepping forward to help.

Secure facilities provide hurricane-proof, wildfire-proof off-site storage for artwork, antiques, and all manner of collectibles for seasonal or rotating storage, as well as ahead of impending disasters.

Other companies help manage such collections — a substantial challenge anytime, but especially during a crisis.

“Knowing where it is, is a huge part of mitigating the risk,” said Eric Kahan, founder of Collector Systems, a cloud-based collection management company that allows collectors to monitor their collections during loans to museums, transit between homes, or evacuation to secure storage.

“Before, insurance was considered the only step in risk management. Now, our client families realize it is one of the many imperative steps in an effective risk management strategy.” — Laura Sherman, founding partner, Baldwin Krystyn Sherman Partners

Insurers also employ specialists in-house. AIG employs four art curators who advise clients on how to protect and preserve their art collections.

Perhaps the best known and most striking example of this kind of direct insurer involvement are the fire teams insurers retain or employ to monitor fires and even spray retardant or water on threatened properties.

High-Level Service for High Net Worth

All high net worth carriers have programs that leverage expertise, loss data, and relationships with vendors to help clients avoid and recover from losses, employing the highest levels of customer service to accomplish this as unobtrusively as possible.

“What allows you to do your job best is when you develop that relationship with a client, where it’s the same people that are interacting with them on every front for their risk management,” said Steve Bitterman, chief risk services officer for Vault Insurance.

Site visits are an essential first step, allowing insurers to assess risks, make recommendations to reduce them, and establish plans in the event of a disaster.

“When you’re in a catastrophic situation, it’s high stress, time is of the essence, and people forget things,” said Sherman. “Having a written plan in place is paramount to success.”

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Another important component is knowing who will execute that plan in homes that are often unoccupied.

Domestic staff may lack the knowledge or authority to protect the homeowner’s assets, and during a disaster may be distracted dealing with threats to their own homes and families. Adequate planning includes ensuring that whoever is responsible has the training and authority to execute the plan.

Evaluating New Technology

Insurers use technologies like GPS and satellite imagery to determine which homes are directly threatened by storms or wildfires. They also assess and vet technologies that can be implemented by homeowners, from impact glass to alarm and monitoring systems, to more obscure but potentially more important options.

AIG’s Poux recommends two types of vents that mitigate important, and unexpected risks.

“There’s a fantastic technology called Smart Vent, which allows water to flow in and out of the foundation,” Poux said. “… The weight of water outside a foundation can push a foundation wall in. If you equalize that water inside and out at the same level, you negate that.”

Another wildfire risk — embers getting sucked into the attic — is, according to Poux, “typically the greatest cause of the destruction of homes.” But, he said, “Special ember-resisting venting, like Brandguard Vents, can remove that exposure altogether.”

Building Smart

Many disaster resiliency technologies can be applied at any time, but often the cost is fractional if implemented during initial construction. AIG’s Smart Build is a free program for new or remodeled homes that evolved out of AIG’s construction insurance programs.

Previously available only to homes valued at $5 million and up, Smart Build recently expanded to include homes of $1 million and up. Roughly 100 homes are enrolled, with an average value of $13 million.

“In the high net worth space, sometimes it takes longer potentially to recover, simply because there are limited contractors available to do specialty work.” — Curt Goetsch, head of underwriting, Private Client Group, Ironshore

“We know what goes wrong in high net worth homes,” said Poux, citing AIG’s decades of loss data.

“We’re incenting our client and by proxy their builder, their architects and their broker, to give us a seat at the design table. … That enables us to help tweak the architectural plans in ways that are very easy to do with a pencil, as opposed to after a home is built.”

Poux cites a remote ranch property in Texas.

Curt Goetsch, head of underwriting, Private Client Group, Ironshore

“The client was rebuilding a home but also installing new roads and grading and driveways. … The property was very far from the fire department and there wasn’t any available water on the property.”

Poux’s team was able to recommend underground water storage tanks, something that would have been prohibitively expensive after construction.

“But if the ground is open and you’ve got heavy equipment, it’s a relatively minor additional expense.”

Homes that graduate from the Smart Build program may be eligible for preferred pricing due to their added resilience, Poux said.

Recovery from Loss

A major component of disaster resiliency is still recovery from loss, and preparation is key to the prompt service expected by homeowners paying six- or seven-figure premiums.

Before Irma, PURE sent contact information for pre-assigned claim adjusters to insureds in the storm’s direct path.

“In the high net worth space, sometimes it takes longer potentially to recover, simply because there are limited contractors available to do specialty work,” said Curt Goetsch, head of underwriting for Ironshore’s Private Client Group.

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“If you’ve got custom construction or imported materials in your house, you’re not going to go down the street and just find somebody that can do that kind of work, or has those materials in stock.”

In the wake of disaster, even basic services can be scarce.

“Our claims and risk management departments have to work together in advance of the storm,” said Bitterman, “to have contractors and restoration companies and tarp and board services that are going to respond to our company’s clients, that will commit resources to us.”

And while local agents’ connections can be invaluable, Goetsch sees insurers taking more of that responsibility from the agent, to at least get the claim started.

“When there is a disaster, the agency’s staff may have to deal with personal losses,” Goetsch said. &

Jon McGoran is a novelist and magazine editor based outside of Philadelphia. He can be reached at riskletters@lrp.com.