Diving into the dynamic world of excess and surplus (E&S) property insurance, we’re thrilled to sit down with Simon Glairy, a seasoned expert in insurance and Insurtech. With a deep background in risk management and AI-driven risk assessment, Simon brings a unique perspective on navigating complex challenges and leveraging technology to transform underwriting processes. Today, we’ll explore his journey through leadership hurdles, innovative strategies for managing high-pressure workloads, and the intersection of technology and human insight in the insurance industry.
How did you feel when you stepped into a leadership role in the E&S property underwriting space, especially knowing you were facing immediate challenges like staffing shortages?
I’ll never forget the mix of excitement and apprehension when I took on that role. Leading a team in E&S property underwriting is no small feat, especially when you’re starting with a smaller crew than expected. My team had shrunk significantly due to the fierce competition for talent, and I knew we had a mountain of work ahead. But honestly, it lit a fire under me. I saw it as a chance to rebuild, to rally the team, and to prove that we could still deliver exceptional results despite the odds. My first thought was to focus on trust—trust in each other and in the tools we had at our disposal.
What was your initial strategy for managing a heavy workload with a reduced team, and how did you adapt to keep things moving forward?
Right out of the gate, we were handling thousands of coverage requests annually with a lean team, which felt daunting. My strategy was twofold: streamline our focus and lean hard on efficiency. I worked to ensure the team wasn’t bogged down by tasks outside our core underwriting responsibilities. We prioritized decision-making speed by using the resources and training we had, and I made it a point to keep morale high. I’d check in regularly, not just about work but to show them I had their backs. Over time, we adapted by refining how we collaborated with other units to offload non-essential tasks, which let us zero in on what we do best—analyzing risks and closing deals.
How do you keep a team motivated when the pressure is on, especially with such a high volume of coverage requests to process?
Motivation under pressure is all about creating a sense of purpose and support. With a workload as intense as ours, I knew burnout was a real risk. I made it my mission to remind the team daily that their work mattered and that they weren’t alone in the grind. We celebrated small wins, whether it was hitting a weekly target or nailing a tough negotiation. I also encouraged open communication—if someone was struggling, I wanted to know so we could tackle it together. Building that trust and camaraderie was key; it turned a high-pressure environment into a space where everyone felt empowered to push through.
Can you share how analytical tools have shaped your team’s ability to make decisions, and what specific data or features you’ve found most impactful?
Analytical tools have been a game-changer for us. They allow us to process massive amounts of data quickly, which is critical when you’re juggling thousands of requests. For instance, we rely heavily on platforms that aggregate risk data and provide real-time insights into market trends and exposure levels. These tools help us assess risks with precision, whether it’s evaluating property vulnerabilities or pricing policies. The most impactful feature for me has been predictive modeling—it gives us a heads-up on potential issues before they become problems, letting us make proactive decisions rather than just reacting.
How do you strike a balance between trusting data-driven analytics and relying on your instincts when underwriting complex risks?
Balancing analytics and instinct is an art. Data gives you a solid foundation—it’s objective and cuts through the noise. But there are moments when the numbers don’t tell the whole story, and that’s where gut feeling comes in. I remember a case where the analytics flagged a deal as borderline, but something about the client’s history and the market conditions didn’t sit right with me. I dug deeper with my team, and we uncovered a pattern of claims that the model hadn’t fully weighted. We adjusted our terms, and sure enough, it saved us from a significant loss down the line. It’s about using data as your guide but never ignoring that inner voice honed by years of experience.
What was your process for identifying tasks to delegate to other units, and how did you get buy-in from those teams to take on additional responsibilities?
Identifying tasks to delegate started with a hard look at what truly required an underwriter’s expertise. Things like preliminary data entry or routine administrative work were eating up our time but didn’t need our specific skill set. I sat down with my team to map out every step of our workflow and pinpointed where we could offload without losing quality. Getting buy-in from other units wasn’t always easy—it took clear communication and a bit of diplomacy. I approached it as a partnership, explaining how this would benefit the broader organization by letting us focus on revenue-generating decisions. Building those relationships and showing mutual value was crucial to making it work.
Your team achieved an impressive financial milestone recently. What key strategies or collaborative efforts do you think drove that success?
Hitting a major financial target like $100 million in gross written premium doesn’t happen by accident. It was a combination of laser-focused strategy and teamwork. We doubled down on efficiency, ensuring every member knew their role and had the tools to execute it. Collaboration with other departments to streamline our workload played a huge part—we couldn’t have done it alone. But honestly, the real driver was the team’s grit. There were late nights and tough calls, but we kept pushing because we believed in the goal. Celebrating progress along the way kept everyone’s energy up, and that collective drive got us across the finish line.
As you’ve expanded your team, what traits or skills have you prioritized in new hires to ensure they mesh with your existing dynamic?
Growing the team meant finding people who not only had the technical chops but also fit our culture. I looked for curiosity—folks who ask questions and want to learn the ‘why’ behind what we do. Adaptability was huge too; E&S is fast-paced, and you’ve got to roll with the punches. I also valued communication skills because we’re a tight-knit group, and being able to express ideas or concerns openly is non-negotiable. During interviews, I’d often throw out real-world scenarios to see how they’d think through a problem. It’s not just about resumes; it’s about finding people who bring energy and balance to the table.
You’ve been involved in developing cutting-edge underwriting software. Can you walk us through the biggest hurdles in creating a tool tailored for underwriters’ needs?
Working on underwriting software, like a catastrophe aggregation platform, has been both exciting and challenging. The biggest hurdle is ensuring the tool is intuitive for underwriters who might not be tech-savvy. You’re dealing with complex data sets—think natural disaster risks or exposure modeling—and translating that into a user-friendly interface is no small task. There were times when early versions were too clunky or didn’t address the specific pain points we face daily. We had to iterate constantly, getting feedback from the team and pushing for simplicity without sacrificing depth. It’s a balancing act, but seeing it come together and save time on decisions makes it worth the effort.
How do you navigate the communication gap between IT, operations, and underwriting teams when developing tools, and what strategies have worked best for collaboration?
The communication gap between IT, operations, and underwriting is real—they often speak entirely different languages. IT thinks in code and systems, while underwriters are focused on risk and clients. My approach has been to act as a translator, breaking down jargon on both sides. I’ve found that regular face-to-face meetings or workshops help immensely—getting everyone in the same room to hash out needs and limitations. For example, when working on a risk analytics tool, I’d sketch out exactly what underwriters needed to see on the dashboard and then walk IT through why that mattered. Building that mutual understanding takes patience, but it’s the only way to ensure the end product works for everyone.
Can you share a specific instance where miscommunication between departments led to a challenge, and how you resolved it to keep a project on track?
Absolutely. Early on in developing an analytics tool, there was a disconnect between underwriting and IT about how data should be displayed. We wanted a specific risk metric front and center because it’s critical for quick decisions, but IT had buried it in a submenu, thinking it was less important based on their design logic. It slowed down testing and frustrated everyone. I stepped in and organized a quick sit-down where we walked through a day in an underwriter’s shoes, showing exactly why that metric mattered. IT got it instantly and reprioritized the layout. That experience taught me the value of showing, not just telling—real-world context cuts through assumptions every time.
As a leader, how do you tailor your approach to meet the unique needs of each team member, and why do you think this is so critical in your field?
Meeting people where they are is at the heart of my leadership style. Every team member brings different experiences, personalities, and career goals, and a one-size-fits-all approach just doesn’t cut it. For a junior hire, I might spend more time mentoring and breaking down complex concepts, while a seasoned underwriter might need visibility or strategic projects to grow. I figure this out by listening—really paying attention to how they communicate and what drives them. In E&S, where stress runs high, this tailored support builds trust and keeps everyone engaged. If I approached everyone the same way, I’d risk alienating half the team and stunting our growth as a unit.
What is your forecast for the future of technology in E&S property underwriting, and how do you see it shaping the industry in the coming years?
I’m incredibly optimistic about the role of technology in E&S property underwriting. We’re on the cusp of a revolution with AI and machine learning, which will take risk assessment to new levels of precision. Tools will not only predict exposures but also suggest tailored solutions in real time, cutting decision times dramatically. I also see automation handling more routine tasks, freeing underwriters to focus on strategy and client relationships. But the human element—judgment and intuition—will always be irreplaceable. My forecast is that over the next five to ten years, the firms that thrive will be those that blend cutting-edge tech with strong personal insight, creating a hybrid model that’s both efficient and empathetic.
