The cyber insurance market is evolving at a pace with which many brokers may struggle to keep up. With new threats emerging daily, the pressure is on to provide clients with policies that fully address their risks.
Jonathan Weekes (pictured) has spent years in the brokerage space and now finds himself on the underwriting side once again, this time as the newly appointed president of BOXX Insurance’s Canadian operations. Having worked closely with brokers at HUB International, he understands their challenges and the need for clear, open communication.
“The one thing I would encourage brokers to do is to communicate regularly with the underwriting community,” Weekes told Insurance Business.
“We generally do a pretty good job in cyber because it's such a small community. But I think there's always that hesitation to speak openly and freely with underwriters because there's that fear of underwriters making changes to their strategy or their appetite.”
Brokers often act as intermediaries between clients and insurers, yet they frequently find themselves navigating an inherently reactive industry. Weekes pointed out that the insurance sector relies on past trends to price risk, but cyber insurance doesn’t operate on a fixed model; it is a moving target.
For brokers, this means keeping up with these changes, understanding how policies are evolving, and ensuring clients aren’t left with outdated coverage. More than ever, brokers must push carriers for transparency in how they are adapting to new risks.
But Weekes stressed that communication has to be a two-way street. Underwriters need to listen to brokers, who are on the front lines with clients. They see the pain points, the gaps in coverage, and the practical challenges clients face when a claim arises.
“I tell my underwriting colleagues, listen to your brokers,” said Weekes. “They’re the first line of communication with clients. If we don't have those lines of communication and we aren't going to listen to their feedback, we won't be able to innovate our products.”
While the cyber insurance market continues to evolve, he said, the fundamentals remain the same: brokers who stay informed, communicate effectively with underwriters, and help clients understand their own risk will be the ones who succeed.
The sheer unpredictability of cyber risks requires brokers to be more proactive in their approach. It’s not enough to rely on outdated policy wordings or assume that insurers will adjust quickly.
Staying informed on emerging threats is also critical. One threat that has drawn Weekes’ attention is supply chain risks. “The CDK breach, which impacted quite a few auto dealers across Canada, is a really good example of how a single IT or technology vendor can ultimately impact several organizations, if not an entire industry,” he said.
That attack, along with others like the CrowdStrike outage, showed how fragile businesses are when a critical service provider is compromised. Brokers need to ensure their clients understand these risks and that their policies account for them.
The industry’s response to these evolving threats has been mixed. Some insurers have tightened terms, while others have broadened coverage, only to later scale it back when losses pile up.
“As a former broker, now in the underwriting side, I almost regret how much I pushed for these policies to be expanded and broadened over the years,” Weekes said. “But I do believe that cyber insurance policies are well-positioned to cover most of the losses or potential losses that our clients are hoping to transfer risk for.”
Coverage alone isn’t enough. The best brokers aren’t just selling policies; they’re working with clients to understand how they can mitigate risk before a claim even happens.
BOXX, for example, has built its business on a model that includes prediction and prevention as much as indemnification. For Weekes, this is where brokers can add significant value, guiding clients through the process of strengthening their security posture and reducing their exposure to cyber threats.
Weekes also mentioned that BOXX is constantly refining its offers in response to the broker feedback and its assessment of the market.
“You’ll find over the next few months, likely towards the end of Q2 and into Q3, we'll be making continuous micro adjustments to our product to ensure we're keeping up with trends based on claims data that we've collected and based on industry data in general,” Weekes said.
Do you agree that open communication is present in Canada’s cyber insurance market? What are some ways the industry can work toward more transparency? Please share a comment below.
