Caroline Thompson

Could you share a bit about your career journey and how you entered the field of underwriting?

I was exposed to insurance early on because my dad worked in the reinsurance industry. During university, I interned at Lloyd's and Hannover Re, which gave me a taste of the industry. After graduating, I applied to many insurance companies and eventually joined Beazley as a claims assistant. Over time, I moved into underwriting, focusing specifically on cyber.

Over time, I moved into underwriting, focusing specifically on cyber.

After gaining experience at traditional carriers, I joined Cowbell, where we built a cyber-focused MGA and established the underwriting function. I recently left Cowbell and I am now the Chief Underwriting Officer at Elixir. 

Congrats on the new role! What will be your main responsibilities at Elixir, and what excites you about joining the team?

Thank you! I'm really excited to get started. My primary responsibility will be to help the team acquire capacity by ensuring we find the right partner who aligns with our goals. In addition to that, I'll be focusing on developing key resources such as forms, guidelines, and underwriting processes to streamline operations. I'll also be responsible for connecting external vendors to Elixir, enhancing our overall capabilities.

What attracted me most to Elixir was its innovative use of AI and co-pilot tools, which significantly enhance efficiency and simplify workflows. Beyond the technology, I was also drawn to the caliber of the team—both co-founders bring outstanding expertise and leadership, with deep, impressive backgrounds in insurance.

Beyond the technology, I was also drawn to the caliber of the team.

With experience across different fields, what unique challenges do you see in cyber underwriting compared to other lines?

Cyber insurance comes with the ever-changing threat landscape and new vulnerabilities, so as underwriters we must stay updated on trends and threats.

Cyber insurance comes with the ever-changing threat landscape and new vulnerabilities, so as underwriters we must stay updated on trends and threats. It's essential to keep educating yourself and understanding the exposures out there. For example, the recent CrowdStrike incident reminded us that even non-malicious threats can affect systems across the country. 

A big part of the job is also making policies easier for clients to understand. Breaking it down in simple terms builds trust and keeps things clear for everyone involved.

When hiring underwriters, what questions do you like to ask to understand their approach to risk?

I like to ask about a challenging renewal risk they’ve handled because it gives me valuable insight into their risk tolerance and decision-making process. It reveals how they weigh the pros and cons of retaining or letting go of a client after a significant loss. If they chose to keep the client, I’m particularly interested in understanding what strategies they employed to help the client recover and improve their position post-loss. 

I like to ask about a challenging renewal risk they’ve handled because it gives me valuable insight into their risk tolerance and decision-making process.

This question not only highlights their ability to manage difficult situations but also shows their approach to long-term client relationships and problem-solving under pressure. It’s a great way to get a sense of their thought process and how they balance business risk with customer loyalty.

What role does innovation play in your approach to underwriting, especially in your new position?

Innovation needs to play a constant role.

As underwriting leaders, we can't be reactive—we need to find ways to identify exposures before they result in a loss. We should lean on data sets to get better terms out faster, with more precision. I'm always looking for ways to challenge the status quo and improve our processes.

As underwriting leaders, we can't be reactive — we need to find ways to identify exposures before they result in a loss.

Is there a piece of advice or a lesson you've learned that every aspiring underwriter should know?

Put your head down and do the work—there are no shortcuts. While some people might coast, it's the hard-working individuals who go further and are happier. 

Stay true to yourself and build your own personal brand. I once had someone tell me to ‘show up more professional,’ but I believe you can be both professional and authentic at the same time.

Also, stay true to yourself and build your own personal brand. I once had someone tell me to ‘show up more professional,’ but I believe you can be both professional and authentic at the same time. I choose to show up as myself, and that’s where my strength lies. So, get out there and build your personal brand—it will take you further than you imagine and give you a deep sense of pride in your career journey.

How do you stay grounded and confident, especially before big events like interviews or panels?

I have several tools in my toolkit, and one of the most important is meditation. Before any significant event—whether it’s a speaking engagement or an important meeting—I take some quiet time to center myself and mentally prepare.

Before any significant event — whether it’s a speaking engagement or an important meeting — I take some quiet time to center myself and mentally prepare.

This practice helps me focus and stay grounded, especially when facing larger audiences or high-pressure situations. I’ve been fortunate to have a strong support system of professional coaches, family, and friends who consistently lift me up. Even when they can’t be there in person, I know they’re rooting for me, and that sense of support makes all the difference.

As Chief Underwriting Officer, what part of the job do you find most fulfilling?

I’m focused on building and creating with a real sense of innovation. I love tackling challenges and connecting with others in the industry. Hiring the right people and helping them grow in their careers is something I care deeply about— it’s rewarding to see people succeed and know that I played a part, even if it was just a small one, in their process.

Hiring the right people and helping them grow in their careers is something I care deeply about.

How do you stay up-to-date with industry trends? Any blogs, podcasts, or newsletters you recommend?

LinkedIn is a great tool, though it's important to filter through all the noise. I also stay current by reading insurance news and following Insurtech updates. I really enjoy Alex Bond's podcast, The Leadership in Insurance — he and his team report on industry developments and Insurtech investments in a way that goes beyond just recruitment.

Do you have any book recommendations that have helped you in your career?

My favorite book is You Are a Badass by Jen Sincero. It's a motivating book about believing in yourself and executing on your goals. While I already held a lot of those beliefs, the book helped me expand on them and put them into action.

I would highly recommend it to anyone looking to grow, both professionally and personally.

What changes do you think we’ll see in the cyber industry in the next 5-10 years?

It’s exciting to see how much the world is beginning to understand the value of cyber insurance, and I believe education will drive even greater adoption.

I think we'll continue to see concerns around catastrophic exposure, but we've also seen resiliency in the face of systemic risks like the CrowdStrike incident. As the industry continues to educate clients and brokers, we'll see more cyber insurance being purchased. It’s exciting to see how much the world is beginning to understand the value of cyber insurance, and I believe education will drive even greater adoption.