Simon Glairy stands at the intersection of traditional insurance wisdom and the cutting-edge frontier of Insurtech. As a recognized authority in AI-driven risk assessment, he has spent his career dissecting how data can be transformed into a shield against corporate volatility. With the landscape of global risk shifting from isolated incidents to interconnected crises, Glairy’s perspective offers a vital roadmap for businesses navigating an increasingly unpredictable world. He understands that in today’s market, simply buying a policy is no longer enough; survival requires a deep, comparative understanding of one’s own vulnerabilities.
This discussion delves into the seismic shift occurring in the insurance industry, where the focus is moving from purely transactional broking to holistic risk advisory. We explore the erosion of departmental silos, the critical “confidence gap” in cyber preparedness among small businesses, and why industry-wide benchmarking has become the primary tool for modern resilience. By examining the integration of climate, geopolitical, and technological exposures, the interview highlights how advanced analytics are reshaping the relationship between brokers, insurers, and the clients they protect.
The traditional corporate model often separates cyber, property, and climate risks into entirely different departments, but we are seeing those walls start to crumble. How is the industry moving toward a more unified, organizational-level view of risk?
The fragmentation we used to see, where IT focused on firewalls while facilities focused on fire sprinklers, is finally becoming a thing of the past. Recent data from a survey of 3,500 leaders across the US, UK, Canada, and Europe confirms this shift, with a staggering 94% of global businesses planning to integrate their insurance and risk management strategies to build resilience by 2026. We are witnessing a moment where environmental, geopolitical, and technological exposures are no longer viewed in isolation but are treated as a single, interconnected pressure point on the board of directors. It is a transition toward portfolio-level thinking that acknowledges a breach in a digital server can be just as devastating to physical operations as a storm. Leaders are moving away from asking if a specific line of business is covered and are instead looking at the health of the total organization. This holistic approach is the only way to survive in a landscape where risks are constantly merging and feeding off one another.
Brokers seem to be moving away from just selling policies toward a role that looks more like strategic consulting. How is the use of data and benchmarking changing the way advice is given to clients?
We are entering what I call the “advisory battleground,” where the most valuable asset a broker provides is no longer the policy itself, but the data-driven insight behind it. According to reports from Q4 2025, there is a clear pivot from transactional broking to a holistic, portfolio-based advisory model that uses advanced analytics to optimize the total cost of risk. By leveraging decades of loss experience across specific sectors, we can now offer a manufacturer or a construction firm a mirror that shows exactly where they stand compared to their peers. This industry benchmarking allows us to challenge historic program designs and stress test earnings at risk with a level of precision we simply didn’t have five years ago. It’s about moving beyond the “what if” scenarios to a concrete “here is how you compare,” which provides a much more compelling narrative for a board of directors looking to justify their mitigation spend.
There is a powerful argument being made that insurance should be more about prevention than recovery. Why is the industry focusing so heavily on stopping events before they happen rather than just paying out claims?
The reality is that by the time you are relying on risk transfer, the worst has already happened, and the emotional and operational toll on a company can be catastrophic even if the check clears. The shift toward prevention is rooted in the idea that comparative data can act as a diagnostic tool to identify vulnerabilities before they are exploited. For example, by using scenario modeling, we can show a client how a specific operational weakness might lead to a total shutdown, allowing them to direct their budget toward mitigation rather than just premiums. This is about strengthening the entire program so that the business is resilient enough to avoid the loss entirely. There is a certain peace of mind that comes from knowing you’ve mitigated a risk based on the hard-earned lessons of others in your industry. When the broker, the client, and the insurer all share a common interest in risk reduction, the entire ecosystem becomes more stable and efficient.
The disparity between how prepared small businesses feel and how prepared they actually are regarding cyber threats is alarming. What do the numbers tell us about this “confidence gap”?
The disconnect in the mid-market and SME space is one of the most dangerous trends I’ve seen in my career. In the United States, 71% of small and mid-sized businesses believe they are fully prepared to handle a cyber incident, yet when you look at the actual data, only 22% report having what we would consider an advanced cybersecurity posture. This false sense of security is a recipe for disaster, especially considering that 43% of all cyberattacks are now targeting small businesses. Even more concerning is the fact that 47% of firms with fewer than 50 employees have no cybersecurity budget at all, and only 17% of US small businesses carry any form of cyber insurance. Cyber isn’t just one person’s job in the IT basement anymore; it’s a multi-layered organizational responsibility that needs to be addressed from the front desk to the executive suite. Benchmarking is essential here because it strips away the overconfidence and shows these firms the reality of the threats their peers are already facing.
Third-party dependencies are becoming a primary vector for breaches, particularly in manufacturing. How does a benchmarking approach help manage the risks that come from outside an organization’s direct control?
The web of vendor dependencies has become so complex that third-party risk has doubled, now accounting for 30% of all recorded breaches. For a manufacturer, your resilience is only as strong as the weakest link in your supply chain, and generic assessments simply don’t capture the nuance of those specific connections. Every organization carries a different set of vendor risks, and that’s where benchmarking adds incredible value by highlighting how others in the same sector are managing similar dependencies. It allows a company to see if their supply chain management is an outlier or if they are following best practices that have protected their competitors from cascading failures. This level of insight is crucial because it moves the conversation from a vague fear of “the unknown” to a targeted strategy for managing specific vendor vulnerabilities. We have to treat our partners’ security as our own, because when they go down, the impact on our operations is immediate and often severe.
With cyber and geopolitics dominating the headlines, there’s a concern that climate risk is being overlooked. How can insurers use their historical data to keep environmental resilience on the corporate agenda?
It is true that climate risk has occasionally fallen by the wayside as boards scramble to react to the latest cyberattack or geopolitical flare-up, but the insurance sector’s analytical assets are the perfect tool to bring it back to the forefront. We have catastrophe models and decades of loss data that allow us to build forward-looking scenarios, testing how something like a prolonged drought or extreme rainfall might ripple through a company’s global operations. It’s not just about the physical damage to a building; it’s about the subtle ways climate change cascades through the supply chain and affects long-term viability. By presenting these risks through the lens of integrated, comparative resilience, we can show executives that climate is not a distant problem, but a current operational threat. The goal is to move from reactive coverage—buying a flood policy after the water is in the lobby—to a proactive stance where the company is built to withstand the weather patterns of the next decade.
What is your forecast for the evolution of risk benchmarking over the next few years?
I believe that within the next three to five years, benchmarking will evolve from an optional advisory service into the foundational standard for every insurance placement in the market. We will see real-time data feeds and AI-driven analytics replace static annual reports, allowing companies to see their risk profile fluctuate in relation to their peers on a week-to-week basis. This transparency will force a massive upgrade in maturity for the SME sector, as the data will make it impossible to ignore the gaps in their cybersecurity and climate preparedness. Ultimately, the role of the broker will be fully redefined as a “resilience architect” who uses these benchmarks to build a fortress around their clients’ balance sheets. The winners in this new era will be those who embrace the data early and treat risk management not as a cost center, but as a primary competitive advantage.
