Welcome to an insightful conversation with Simon Glairy, a renowned expert in insurance and InsurTech, with a deep focus on risk management and AI-driven risk assessment. With decades of experience in the global and Lloyd’s markets, Simon brings a wealth of knowledge on leadership transitions, strategic growth, and the evolving landscape of reinsurance. Today, we dive into themes such as navigating major corporate shifts, leveraging extensive industry experience for innovation, and envisioning the future of established firms in a competitive market. Let’s explore his perspectives on these critical topics.
What drew you to the idea of stepping into a leadership role at a well-established firm like MS Amlin, and what excites you most about such an opportunity?
I’ve always been fascinated by the chance to lead a company with a strong legacy and a solid reputation in the market. What excites me most is the opportunity to build on that foundation while driving innovation. A firm like MS Amlin has a unique position in the Lloyd’s market, and the prospect of steering it into its next chapter—blending tradition with forward-thinking strategies—is incredibly motivating. It’s about honoring the past while seizing new opportunities in a rapidly changing industry.
How would you approach building on a period of strong financial performance, such as the kind seen under a transformative leader?
Strong financial performance is a testament to solid strategy and execution, so my approach would be to first understand the key drivers behind those results. I’d focus on maintaining the momentum by reinforcing successful practices, whether that’s disciplined underwriting or smart capital allocation. At the same time, I’d look for areas to enhance efficiency or explore new growth avenues, like emerging risks or untapped markets. It’s about striking a balance between preserving what works and challenging the status quo to keep the business agile.
With over three decades in the reinsurance and insurance sector, what are some of the most valuable lessons you’ve learned that would guide your leadership?
One of the biggest lessons I’ve learned is the importance of adaptability. The industry has seen massive shifts over the years—whether it’s regulatory changes, technological advancements, or evolving risk profiles—and you have to be ready to pivot. Another key takeaway is the value of relationships. Trust and collaboration, whether with brokers, clients, or your own team, are the bedrock of this business. Finally, I’ve learned to never underestimate the power of data. Informed decision-making, especially in underwriting, can make or break a company, and that’s something I’d carry into any leadership role.
Having managed large, diverse portfolios in past roles, how do you think that experience would shape your strategy as a CEO?
Managing multi-line portfolios teaches you how to juggle competing priorities and risks, which is critical as a CEO. My experience has honed my ability to assess where to allocate resources for maximum impact, whether that’s investing in a particular line of business or pulling back from underperforming areas. It also taught me the importance of fostering a cohesive team culture across different functions. As a CEO, I’d use that insight to ensure alignment across the organization, making sure every department is pulling in the same direction while still respecting their unique challenges.
How do your past underwriting roles inform the way you’d tackle the broader responsibilities of leading a global insurer?
Underwriting roles ground you in the technical heart of the business—understanding risk, pricing it right, and managing exposure. That foundation is invaluable when you’re making high-level strategic decisions because you can see how they ripple down to the day-to-day operations. For instance, I’d be very focused on ensuring that our underwriting discipline aligns with our broader goals, like profitability or market expansion. At the same time, those roles taught me patience and precision, which are just as important when dealing with stakeholders or setting long-term visions as they are when analyzing a complex risk.
What’s your vision for taking a respected company to the next level of its development in today’s market?
My vision would center on sustainable growth and innovation. That means deepening our expertise in core areas while also exploring how technology—like AI for risk assessment—can give us an edge. I’d want to position the company as a leader in addressing emerging risks, whether that’s cyber threats or climate-related challenges. Additionally, I’d focus on strengthening our global presence by building strategic partnerships. Ultimately, it’s about creating a company that’s not just reacting to the market but shaping it, all while staying true to its reputation for reliability and excellence.
How do you see the support of a larger parent group influencing your strategic decisions as a leader?
Having the backing of a larger group is a tremendous advantage. It provides financial stability, access to broader resources, and often a wider network to tap into for expertise or opportunities. I’d leverage that support to take calculated risks—perhaps entering new markets or investing in tech—that might be harder for a standalone entity. At the same time, it’s crucial to maintain the company’s unique identity and agility. So, my strategy would involve close collaboration with the parent group to align on big-picture goals while ensuring we’re nimble enough to respond to local market dynamics.
Looking at the global reinsurance and insurance landscape, what do you see as the biggest challenges and opportunities ahead?
The biggest challenge right now is the increasing complexity of risks—think cyber attacks, climate change, and geopolitical instability. These are hard to model and can lead to significant volatility if not managed well. On the flip side, these same challenges present huge opportunities. Companies that can innovate in how they assess and price these risks, or develop new products to address them, will stand out. There’s also a massive opportunity in digital transformation—using data and AI to streamline operations and improve customer experience. The firms that get this right will lead the pack in the coming years.
How do you prepare for a significant leadership transition, especially when there’s a gap before officially starting the role?
Preparation is all about immersion and listening. Even before stepping into the role, I’d spend time studying the company’s performance, culture, and market position. I’d reach out to key stakeholders—employees, clients, and partners—to understand their perspectives and expectations. It’s also a time to reflect on my own goals and how they align with the company’s direction. I’d work closely with the outgoing leader to ensure continuity, asking for insights on what’s worked and where there’s room for improvement. That groundwork helps make the transition as seamless as possible.
What’s your forecast for the future of the global reinsurance market over the next decade?
I believe the global reinsurance market is headed for a period of significant transformation over the next ten years. We’ll see an acceleration in the use of technology—AI and machine learning will become standard for risk modeling and claims processing, making the industry more efficient but also more competitive. At the same time, the rise of non-traditional risks, like cyber and environmental challenges, will push reinsurers to rethink their offerings and capacity. I also expect consolidation to continue as firms seek scale to manage rising costs and capital demands. Ultimately, those who can balance innovation with disciplined underwriting will thrive in this evolving landscape.
