Breaking systems: one industry professional’s journey into cyber insurance

A knack for “breaking systems” as a teenager set Neal Jardine on a path into the cyber insurance space.

During his university years, Jardine, chief cyber intelligence and claims officer at BOXX Insurance, was hired to maintain the student network and provide help and support to teachers across campus. After university, he joined CGI, an information technology consulting company, building software, processes, and scripts.

Within a short time, Jardine says he “just got tired of sitting in a server room. I always say, ‘Great air conditioning, no windows.’

“So, you’re sitting there in this room focused on computers and I found the part I really liked about the computers was helping people understand how to use them and get out of problems [using] them.”

That realization inspired his move into insurance, where he saw an opportunity to help translate complex systems and technologies into real-world solutions.

When Jardine spotted a job posting for a property road adjuster, he made his move. “I knew this would get me out of the server rooms and in front of people again doing what I enjoyed, blending technology and people,” Jardine says.

This year, he’s one of six winners of the Insurance Institute of Canada’s 2025 National Leadership Awards in the Emerging Leaders category.

Jardine ended up at Crawford & Company (Canada) Inc. working on construction and infrastructure claims in the field. When IT-related losses or complex digital claims arose, he was the go-to expert. In 2014, Jardine played a key leadership role in building Crawford’s cyber practice across both Canada and the U.S.

“I quickly fell in love with cyber,” he says. “Here I was back in my realm of investigating how attackers got into servers and systems, understanding the attack, and understanding the effect on the businesses.”

After several years, he was approached by BOXX Insurance, which was looking to tackle cyber risk in a new, more proactive way.

“We know that many clients have never experienced a cyberattack before, so we needed a new approach to claims handling that allowed clients to report a potential event and receive help without making a claim,” Jardine says. “The process we built is very much around reaching out to a client throughout the policy period, engaging with them, letting them know what we see, letting them know what hackers see, and trying to stop those events before they happen.

“We’re essentially the day and night security guard watching the entrances to their digital world,” he says. “Looking back it makes me smile; it’s a lot of what I was doing in my university days, trying to catch the cybercriminals who were using the university network to trade movies online or take advantage of our high speed internet.”

As for trends in the cyber space, Jardine says he’s now seeing artificial intelligence being weaponized to identify relationships between companies to better exploit them. At the same time, cyber policies are expanding to protect clients throughout the entire policy term by adding in threat intelligence and risk coaching, for example.

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“It means the small businesses aren’t having to spend thousands of dollars on having threat intelligence feeds, they’re getting all that through their insurance policy at no extra cost leaving them with more money to invest in their business,” Jardine says.

He also sees insurance’s reputation changing as it continues to help policyholders, whether they experience a cyberattack, wildfire, flood or other disaster. “We’re going to see the expansion of insurance in people’s worlds as climate change increases and we move more and more into a digital world requiring more protection.”

While insurance will be more in front of people as it evolves, a lot is going on behind the scenes.

“A big part of what I love about the industry is just how interconnected we are and how well we all communicate risks,” Jardine says. “That’s the part that I find is most rewarding and impactful: doing what insurance does best, helping people and businesses in their time of need.”

Jason Contant

Jason has been an award-winning journalist with Canadian Underwriter for more than a decade, including the past three years as associate editor and, before that, as digital editor for seven years.