A career that started as a placeholder and became the master plan

Stephen, before insurance entered the picture, where did you imagine your career heading?   

I studied criminal justice at university and was seriously considering law school. After graduating, I had some time to think things through, took my LSATs, and started working in the meantime.   

That’s how insurance entered the picture. I took a role with an insurance company in personal lines, mainly to earn and buy myself some thinking time. What I didn’t expect was that an opportunity would come up shortly after to join Endurance, back in 2014, before the Sompo acquisition.   

What drew you to that opportunity at the time?   

It felt like a chance to build something. The Company was starting its Retail Property group, and I joined as a technical assistant to a very small team, there were just three of us at the time. I had limited exposure to commercial insurance, so I was learning everything from the ground up.  

Very quickly, I realized this was a career path I wanted to pursue. The work was interesting, the learning curve was steep, and from a work‑life balance perspective, it felt sustainable, not just for the moment, but long term. Once I committed to it, I never really looked back.  

You were part of our very first trainee program. What was that experience like?   

About a year or so into my role, the company decided to launch its first trainee program. I put my name forward and was selected as part of the inaugural class. It was an eighteen‑month program and still taking shape as we went through it.  

But it was invaluable. It gave me a structured foundation in underwriting and accelerated my development. I became part of the first graduating class, and that experience set the tone for everything that followed in my career.  

After the program, you found yourself in a different team. How did that happen?   

Instead of going back into shared and layered retail property, I made the decision to pivot into a new team that was just being set up - the middle market retail property group. It felt familiar in a good way, another opportunity to plant a flag and help build something from scratch.   

I spent around five years in that group. We started with zero premium, and by the time I moved on, the book had grown significantly. There was a strong team around it and being part of that growth was incredibly rewarding.   

After the middle market build‑out, I was asked to help establish a non‑catastrophe product within the E&S Property team. That’s where I am today.    

How do you explain your role to someone unfamiliar with insurance?   

I usually say that I assess risk and help provide insurance solutions for commercial properties. That can mean anything from small family‑owned businesses to global corporations with billions in insured values.   

The accounts I typically see are complex. Many have natural catastrophe exposure or fire hazards that make them difficult to insure. Often, no single carrier wants to take the entire risk, so the solution involves structuring and sharing that exposure thoughtfully.   

A big part of my job is working closely with brokers - reviewing submissions, engineering reports, catastrophe modelling, and then shaping policy terms and pricing to come up with a solution that works for everyone involved.   

What do you enjoy most about your work?   

Honestly, it’s the combination of people and problem‑solving. The relationship side of the job is great. Building long‑term partnerships with brokers, getting to know them beyond transactions, and collaborating on tough accounts.   

At the same time, the analytical side keeps things interesting. I work on technical manufacturing risks, so one day I might be observing how steel rebar is produced, and next I’m reviewing a semiconductor fabrication plant or a food manufacturing operation. The variety means no two days feel the same.   

What do you think you bring to the business personally?   

I think my value lies in experience and perspective. I’ve worked across shared and layered property, middle market, and now E&S, which gives me a broad understanding of how different pieces fit together.   

I’ve also spent a lot of time training others—walking teammates through complex accounts, helping them think creatively about structure, pricing and wording. Being able to draw on past experience and pass that knowledge on is something I take pride in.   

After more than a decade, what keeps you at the Company?   

I’ve always felt supported. I’ve raised my hand for initiatives, even when they weren’t directly in my job description, and the company has consistently recognized that.   

Sompo rewards people who are willing to get involved, whether that’s new systems, rating platforms, or broader projects. Those contributions don’t go unnoticed, and they lead to growth, promotions, and new opportunities.   

What sets Sompo apart for you, especially in a competitive market?   

Despite its size, the organization still feels relatively flat. There’s an entrepreneurial mentality that hasn’t been lost, even as the business has grown.    

Many people here have come from larger institutions, but there’s still a sense that you can make an impact, be seen, and shape outcomes. That balance of scale and agility is something I don’t take for granted.   

Looking ahead, what keeps you excited about the future?   

There’s still so much ahead. In the US especially, it feels like we’re only scratching the surface of what Sompo can become. Every year brings something new - new products, new teams, new initiatives. If you enjoy building and evolving, there’s always another chapter starting.   

A sunny day in Barcelona

And outside of work, what does life look like?   

My wife and I live in Jersey City with our young son, and that’s where most of my time goes outside work. I enjoy cooking – pizza is a particular passion, and experimenting with recipes. Travel, seeing friends, and spending weekends together help keep things balanced. It’s important to me that my career supports, rather than competes with life outside the office.   

Final question. Pineapple on a pizza?    

Absolutely not.    

Thank you for this insightful conversation, Stephen.