Reinventing a career, one bold step at a time

Kristi, your career path into insurance wasn’t exactly traditional. How did it all begin?  

My background is in psychology and sports management. I spent the early part of my career working in sports, everything from operations to marketing and community relations. I loved the industry, but I quickly realized the work‑life balance wasn’t sustainable if I wanted a family.  

From there, life made a few decisions for me. My husband’s job required a move, and that pushed me to explore other industries. I worked in healthcare marketing and then sales, so most of my career always had some element of people, persuasion, and relationship‑building. Insurance wasn’t on my radar...until it was.   

That shift into insurance came in an unexpected way?  

Very unexpected. I was talking to my local insurance agent to move my own policies, and during our conversation she said, “Have you ever thought about selling insurance?” I hadn’t, but she saw something in me and kept encouraging the idea.  

I did try it briefly on the property and casualty side, which I realised wasn’t for me, but I loved the stability insurance offered: the benefits, the hours, the structure. When a friend later told me about an opening at Sompo in Surety - something I admittedly knew nothing about - it immediately felt like an opportunity worth taking.   

What made Sompo the right choice at that point in your life?   

Sompo is a large, well‑established company, but it offered exactly what I was looking for: opportunity, support and long‑term stability. I joined as an underwriting assistant in Surety, fully aware that I was stepping back in my career in order to move forward. I had no experience in surety and had to learn everything from the ground up, but that wasn’t intimidating. Reinventing myself was something I’d done before.    

Your progression since then has been impressive. How did that happen?   

The short answer is people. I have never worked anywhere else where I felt so included, valued and genuinely heard. Sompo is extremely merit‑based, and I’ve always been someone who commits fully, if I’m doing something, I’m giving it 100%.   

From day one, leaders were asking me about my aspirations. They wanted to know where I saw myself growing. Initially, I didn’t have all the answers, I was still learning the business, but I knew I enjoyed the operational and support side more than underwriting itself.   

Just over a year in, a team lead position became available. I had leadership experience from previous roles, so I put my name forward, even though I wasn’t sure if I was “ready” yet. I was offered the role, and from there everything accelerated.   

How did you feel about your early days in the world of surety?    

Surety was undergoing significant evolution, and I had the chance to be deeply involved. Not just as a people leader, but in shaping how the transactional side of the business worked.   

That’s how I became closely involved with the Digital Hub project. Being part of something transformational, while also learning how leadership works in a corporate environment, was a huge opportunity.   

For those unfamiliar with surety, how would you explain what you do today?

I usually start with a very basic idea of surety. For example, when you hire a contractor and hear they’re “licensed and bonded,” the bonded part is us. Surety bonds act as a guarantee that contractors will fulfil their obligations. 

That protection is especially critical for public projects, things like schools or government infrastructure. My team supports underwriters by handling policy administration, billing, changes, and agent support. Essentially, we enable underwriters and agents to focus on bringing in and executing business effectively.   

What part of the role do you find most rewarding?  

People, without question. Leadership is a double-sided coin – it can be challenging, but it’s also incredibly fulfilling. Seeing people grow, develop, and succeed is a privilege.   

You’ve spoken with pride about the Surety Digital Hub. Why is it such an important achievement for you?   

The Digital Hub is an agent‑facing portal that allows agents to quote and execute bonds quickly, often while clients are sitting right in their office. It dramatically improves customer experience and gives agents more autonomy and confidence.   

What really makes me proud is the impact. Every month last year, production through the Digital Hub more than doubled what we’d seen on previous platforms. It’s not just technology for technology’s sake, it’s enabling growth, efficiency and better relationships with agents.  

Looking ahead, what excites you most about the future?   

I’m excited about learning more. My recent promotion will allow me to deepen my understanding of underwriting within the Digital Hub, and that’s an area I’m really looking forward to expanding into.   

More broadly, unless something truly drastic changes, I can honestly say I’d love to retire at Sompo. The leadership, the culture, and the opportunity to keep growing make this a place I can see myself staying long‑term.   

Finally, how would you inspire others to look into insurance as a viable and long-term career choice?    

I’d talk about balance, challenge, and opportunity. Insurance offers meaningful careers that still leave room for family, travel and life outside work.   

It’s about sharing real stories, showing how this industry can offer stability without boredom, and growth without burnout.   

Life 'on the Edge' - visiting NYC with family

And outside of work, what keeps you grounded?   

My family. My husband, my son, and our Boston Terrier are my world. We love traveling, hiking, trying new food, visiting family in Alabama, and making the most of our time together. We work hard to play hard.    

Kristi, thank you very much for opening the door to your interesting career journey.