I’m thrilled to sit down with Simon Glairy, a renowned expert in insurance and Insurtech, who brings a wealth of knowledge in risk management and AI-driven risk assessment. With a career spanning both carrier and distribution sides of the industry, Simon has a unique perspective on how technology is reshaping insurance for small businesses. In our conversation, we dive into the challenges small business owners face in securing coverage, the transformative role of technology in the insurance space, the empowerment of agents through Insurtech platforms, and the exciting opportunities created by ecosystem partnerships. Join us as we explore how the future of insurance is becoming faster, clearer, and more trust-driven.
How do you see the insurance landscape for small businesses in the U.S., and why do so many of them struggle to get adequate coverage?
The insurance landscape for small businesses in the U.S. is both a challenge and an opportunity. A staggering number of these businesses—often microbusinesses or sole proprietors—remain uninsured or underinsured, not because they don’t value protection, but because the system wasn’t designed with them in mind. Many owners are so focused on day-to-day operations that they lack the time or know-how to navigate complex insurance requirements. They often don’t know what coverage they need or who to trust, and that uncertainty can be paralyzing. Traditional models cater more to larger enterprises, leaving smaller players with limited affordable options despite real risks and contractual needs. It’s a gap that’s long overdue to be addressed.
What are some of the key obstacles small business owners face when trying to understand and meet their insurance needs?
One of the biggest obstacles is simply a lack of expertise. Small business owners are often wearing multiple hats—managing finances, operations, and customer relations—so diving into the nuances of insurance feels like a daunting task. They might not know the difference between general liability and professional liability, or how much coverage is enough. Additionally, the process can feel opaque; comparing options or understanding policy terms isn’t always straightforward. Cost is another hurdle—many assume insurance is out of reach financially, especially when traditional models aren’t tailored to their scale. This often leads to them overlooking critical protections.
In what ways is technology reshaping how insurance agents serve small business clients?
Technology is a game-changer for agents working with small businesses. Digital tools like quote-and-bind platforms and AI-powered underwriting are streamlining the entire process, making it faster and more accessible. Agents can now tap into a wider range of carrier options without the heavy administrative burden of redundant data entry or complex policy management. This means they can serve more clients in less time while still offering tailored advice. Beyond efficiency, tech creates a better customer experience—think digital-first quoting journeys that let business owners get coverage quickly, often without even picking up the phone, while still having access to a licensed expert when needed.
Can you share some specific examples of digital tools that are making insurance more accessible for small businesses?
Absolutely. Digital quote-and-bind platforms are a prime example; they allow business owners to get multiple quotes in minutes and finalize coverage online, which is a huge time-saver. AI-driven underwriting tools are another—by analyzing data quickly, they help assess risks and price policies more accurately for small businesses, even those with unique needs. Then there are automated workflows and digital documentation systems that cut down on paperwork, making the process smoother for both agents and clients. These tools aren’t just about speed; they’re about breaking down barriers that once made insurance feel out of reach for smaller operations.
How do Insurtech platforms help bridge the gap between traditional insurance agents and the modern needs of small business clients?
Insurtech platforms act as a vital link by combining the best of both worlds—traditional agent expertise and digital efficiency. They equip agents with tools to handle the digital demands of today’s small business owners, like instant quoting or centralized policy management, without losing the personal touch. These platforms allow agents to deliver a modern, responsive experience, where clients can engage on their terms—whether that’s online or through a conversation. At the same time, they maintain trust and personalization, which are cornerstones of agent-client relationships, ensuring that tech enhances rather than replaces the human element.
What role do ecosystem partnerships play in expanding access to insurance for small businesses?
Ecosystem partnerships are incredibly powerful because they meet small businesses where they already are. Instead of relying solely on traditional insurance channels, providers are integrating solutions into platforms like accounting software, payment systems, or contractor marketplaces that entrepreneurs use daily. These partnerships make insurance feel less like a standalone product and more like a natural part of running a business. They create touchpoints for offering relevant, timely coverage—think a contractor instantly sharing a certificate of insurance through a marketplace platform. It’s about solving real problems and building trust, not just pushing a sale.
Can you walk us through a specific example of how one of these partnerships has solved a real-world problem for small businesses?
Sure, let’s take the example of a contractor marketplace platform. These platforms often match contractors with homeowners for jobs, but there was a gap in visibility—neither party knew if the job progressed, if documents were exchanged, or if trust was established. By integrating a digital insurance solution, contractors could share certificates of insurance directly within the platform. This not only solved a documentation issue but also built trust with homeowners, showing proof of coverage instantly. It removed friction from the process and turned insurance into a seamless part of the transaction, benefiting everyone involved.
How do you see automation and human expertise working together in this evolving insurance model for small businesses?
Automation and human expertise are complementary in this new model. Automation handles the repetitive, time-consuming tasks—like data entry, initial quoting, or policy documentation—freeing up agents to focus on what they do best: advising clients. For small businesses, this means faster transactions; over 80% of policies are now bound without a phone call when the process is intuitive. But human expertise remains crucial for complex scenarios or when a business owner needs reassurance. It’s about balance—tech speeds things up, while agents provide the trust and tailored guidance that automation can’t replicate.
What’s your forecast for the future of small business insurance as technology and partnerships continue to evolve?
I’m incredibly optimistic about the future of small business insurance. As technology advances, we’ll see even more intuitive tools—think smarter AI for risk assessment or fully integrated platforms where insurance is just a click away in everyday business apps. Partnerships will deepen, embedding coverage into more ecosystems, making it a no-brainer for entrepreneurs. The focus will shift further toward transparency and trust, with digital-first experiences backed by human support. Ultimately, I believe we’re heading toward a landscape where no small business is left uninsured or underinsured, because the barriers of cost, complexity, and access will be dismantled through innovation and collaboration.
