A passionate leader with a ‘teaching soul’

Simon, you’ve been with the company for more than a decade. How did your journey begin?   

I joined the company back in 2014, coming from a broking company where I was an AVP, still relatively early in my career. Reinsurance is a very small industry, and reputation travels fast. I remember my first day vividly: people already had expectations of me, even stories about things I’d done before I’d ever met them. It was surreal but also motivating. I felt a strong responsibility to live up to that trust. The team I joined was small, and I was one of the younger people there, which pushed me to prove myself, not just technically, but as a collaborator.   

Can you take us through your development over the years and what shaped your progress at Sompo?  

From early on, I made a conscious effort not to stay siloed. Actuarial roles are often seen as purely functional, but I wanted to be engaged with the wider business, with underwriting, claims, accounting, operations, legal. 

That approach really shaped my career. As the business went through acquisitions, the culture stayed largely intact, but the scale and ambition changed. Around that time, I was promoted to VP, which felt like a real shift. It wasn’t just a title change; the responsibilities were fundamentally different.   

Then, after several years, I was promoted to SVP. That one truly caught me by surprise. It brought back that same feeling from my first day – honor, pressure, and reflection about why I’d been trusted with that role.   

How would you explain what you do to someone without knowledge of reinsurance and actuarial?   

I usually explain it in layers. First, reinsurance itself - insurance for insurance companies. It helps carriers manage extreme risks like hurricanes or earthquakes by spreading that exposure across multiple companies.   

Then there’s the actuarial side. In this math-related field, I use statistics, data and business knowledge to help the company understand risk: how often losses might happen, how big they could be, and how we should price for them. We also validate whether things are working as expected and flag areas of concern.   

Finally, as an SVP, a large part of my role is leadership – managing, mentoring and developing people. Increasingly, that means teaching communication, business thinking and collaboration, not just technical skills.   

What part of your role do you enjoy most?   

Training, without question. Early in my career, I loved teaching technical concepts and breaking down complex ideas. Over time, that evolved into something deeper. Now I spend much more time teaching soft skills: how to communicate clearly, how to support others, how to think holistically about the business.   

I’ve always had a ‘teaching soul’. When I was younger, I wanted to be a teacher. I didn’t end up following that path formally, but I get to live that passion every day. Seeing someone grasp a difficult concept, that moment when the light bulb goes on is incredibly rewarding.   

It truly would be hard to find something better than that ‘light bulb’ moment.    

There is something even better. When someone I’ve trained becomes better than me at something. That’s the best outcome possible. It means I’ve done my job well.   

Beyond technical expertise, how do you think you add value to your team and the Company?    

That’s something I reflected on deeply when I became an SVP. The conclusion I reached was that my value isn’t purely technical, there are many people who can provide that technical expertise or be trained to do so.    

My real contribution is connection. I build strong relationships across underwriting, claims, operations, legal, and other departments. I actively look for ways to connect people and ideas. Sometimes that starts with something as simple as walking the floor and saying hello to everyone each morning.   

Those connections create opportunities – new initiatives, better collaboration, better decisions. I see myself as a bridge between parts of the organization that might not otherwise interact.   

You have had not only a successful, but also long career at Sompo. What keeps you at the Company?    

People, first and foremost. The environment here is collaborative and intellectually stimulating. This is not your stereotypical actuarial job, where you sit alone crunching numbers all day. You solve problems together.   

I also have a lot of respect for the leadership team. They invest in people, they’re fair, and they reward effort and curiosity. I’ve seen that not just in my own career, but across the organization.   

What does Sompo do particularly well when it comes to retaining talent?   

They don’t let careers go stale. Instead of forcing people into fixed roles, they create opportunities that align with what individuals are good at and excited about, even if that means inventing something new.   

You see actuaries move into ceded (reinsurance) or into underwriting, underwriting assistants move into business development, people stepping into leadership earlier than they expected. That flexibility keeps people engaged.    

A magical reinsurance offsite at Disney World

What excites you about the future?   

We’ve reached a scale where we’re significant, but we still operate with a small‑company mindset in terms of how we approach innovation and adopting new ideas to do things better. There’s enormous potential in how technology, AI, and cross‑functional collaboration will shape the next phase. 

Personally, I’m most excited about seeing my team grow. Many of the people I’ve trained started at entry level. Watching them step into senior roles and leadership positions and earning their chance to shine - that feels like the natural continuation of my teaching soul.  

And outside work- what brings you joy?   

Puzzles, board games, escape rooms – anything mentally stimulating. I even track escape room success rates in a spreadsheet.    

On the other end of the spectrum, I’ve practiced martial arts for nearly twenty years and currently train in Brazilian Jiu‑Jitsu. It’s a balance of mind and body, strategy, and discipline.    

Simon, thank you for explaining everything in such a clear and concise way. Regarding those escape room spreadsheets, we are going to need to see them to believe them.