I’m thrilled to sit down with Simon Glairy, a trailblazer in the world of insurance and Insurtech, whose expertise in risk management and AI-driven risk assessment has positioned him as a thought leader in modernizing highly regulated industries. With decades of hands-on experience, Simon has a unique perspective on how technology is reshaping the future of insurance and beyond. In this conversation, we dive into his journey, the transformative power of AI, the mission behind his ventures, and his insights on backing the next generation of innovators in complex markets. We also explore how he supports early-stage companies and what he sees as the biggest opportunities—and challenges—on the horizon.
Can you share a bit about your journey in the insurance industry and what motivated you to focus on innovation and venture capital?
Absolutely, I’ve spent over two decades immersed in the insurance world, starting with roles that gave me a ground-level view of how risk is managed and evolving into leadership positions where I could see the bigger picture. Some of the most defining moments came from navigating major industry shifts—like the increasing complexity of risks and the slow adoption of technology. I eventually ran a national brokerage and saw firsthand the gaps in how traditional systems handled modern challenges. That experience, combined with a passion for solving systemic problems, pushed me into venture capital. I wanted to empower founders who are building the tools to address these gaps and transform the industry for the better.
What drives the mission of your work in Insurtech, and how do you differentiate your approach from other players in the venture space?
At the core, my mission is to back early-stage companies that can bring real, lasting change to industries like insurance and healthcare—sectors where trust and reliability are non-negotiable. What sets my approach apart is a deep focus on highly regulated markets. These are spaces where innovation is hard but incredibly impactful when done right. I look for “transformational change,” which to me means solutions that don’t just tweak existing systems but fundamentally rethink how risk is understood and managed. It’s about resilience and creating tech that can handle the complexities of today’s world.
There’s a lot of buzz around AI, particularly generative AI, in insurance. Can you elaborate on why you see it as such a game-changer?
AI, and generative AI in particular, is a turning point for insurance because it tackles inefficiencies that have plagued the industry for years. Think about underwriting or claims processing—tasks that traditionally rely on mountains of data and manual effort. AI can analyze patterns at a scale and speed humans can’t match, leading to faster, more accurate decisions. It’s also opening doors to personalized policies and predictive risk models. That said, it’s not without challenges. The regulatory landscape is tight, and there’s always the risk of over-reliance on algorithms if they’re not transparent or well-tested. Balancing innovation with accountability is key.
When it comes to the companies you choose to invest in, what are the key traits or focuses you prioritize?
I’m drawn to early-stage companies that are solving real pain points in regulated industries. That often means tech-driven solutions in areas like insurance, financial services, or healthcare. Beyond the idea itself, I look for founders who have a clear vision and the grit to execute it. They need to understand the nuances of their market—regulation, trust, scalability. I also weigh the balance between cutting-edge innovation and practical reliability. A flashy tool is useless if it can’t be trusted in high-stakes environments.
You’ve made several investments already. Can you tell us about one or two that particularly excite you and why?
I’m thrilled about a couple of companies in my portfolio that embody the kind of change I want to see. One is focused on leveraging AI to streamline complex processes in insurance, which has the potential to save time and reduce errors on a massive scale. Another is building accessible solutions to help businesses manage risk in smarter ways. What excites me most is how these companies align with my vision of modernizing resilience—they’re not just innovating for the sake of it; they’re addressing foundational needs with tech that’s both forward-thinking and dependable.
Beyond financial backing, how do you support the startups in your portfolio to help them succeed?
Capital is just the starting point. I bring my industry experience to the table to help with things like go-to-market strategies, navigating regulatory mazes, and building the right team. For instance, I’ve worked closely with companies to refine how they position themselves to stakeholders in highly regulated spaces, ensuring they build trust early on. I’ve also connected founders with industry experts from my network to tackle specific hurdles, whether it’s a compliance issue or scaling operations. It’s about being a partner, not just an investor.
Looking back at some of your early successful investments, what do you think gave you the edge in identifying those opportunities?
I think it comes down to a mix of deep industry knowledge and pattern recognition. Having operated in insurance for so long, I can spot where the pain points are and which solutions have the potential to redefine a category. I also focus on founders who are obsessive about their problem space—they live and breathe it. Lessons from past investments have taught me to prioritize adaptability; markets like these shift fast, and companies need to pivot without losing sight of their core mission. That’s something I emphasize with every new investment.
What is your forecast for the future of Insurtech, especially with the rapid advancements in technology we’re seeing today?
I’m incredibly optimistic about Insurtech’s future, but it’s going to be a wild ride. Technology like AI and machine learning will continue to disrupt traditional models, making insurance more predictive, personalized, and efficient. We’ll see more integration of real-time data—think IoT devices feeding into risk assessments. But the flip side is that regulation will tighten as these technologies scale, and trust will remain a huge hurdle. My forecast is that the winners will be companies that can innovate while building robust, transparent systems that regulators and customers alike can rely on. It’s a challenging balance, but the potential for impact is enormous.
