Jennifer Hoolehan Kyung

Can you walk us through your career journey and what drew you to underwriting?

I started in property and casualty underwriting right out of college. I had a classmate from Northwestern University who was a year ahead of me and went into underwriting, and she encouraged me to explore it. So, I took a look, and it really clicked for me.

What I loved about it was that it felt like running my own business—you manage your own P&L, identify your prospects, create solutions, develop pricing, and manage the profitability of your book.

The complexity of insurance products was really interesting too, and before I knew it, I was hooked. I’ve since worked on both the consulting and carrier sides, always staying in underwriting because there’s never a shortage of problems to solve! 

You’ve held prominent roles in underwriting at Zurich North America, USAA, and EY, to name a few. Looking back on your career, what achievement are you most proud of?

‍That’s a great question! When I look back, I feel most proud of the teams I’ve worked with and developed—especially the women leaders I’ve seen grow into directors and executives in insurance. Watching them take on new challenges and flourish has been incredibly rewarding.

Another thing I’m proud of is my role in pushing underwriting into the future. I’ve consistently worked to drive the capabilities needed to shape the next generation of underwriting, and it’s been so fulfilling to have a voice in that movement.

What’s been the most surprising change you’ve witnessed in the underwriting industry during your 30 years in the industry?

‍If there’s one thing that stands out, it’s the level of volatility we’re dealing with now. Over the last 30 years, we’ve always managed risk, but today’s risks are unpredictable.

If there’s one thing that stands out, it’s the level of volatility we’re dealing with now. Over the last 30 years, we’ve always managed risk, but today’s risks are unpredictable.

The level of volatility and the amount of agility that underwriters need to keep pace is changing very rapidly. As underwriters, we’ve always been agile and skilled at mitigating and managing risk—that’s what we do. However, the pace of change and the level of volatility now are like nothing we’ve ever seen before.

For example:

1. On the property side, weather volatility is changing rapidly, and we don’t have models to help with that.
2. Supply chain and connectivity in our global environment have significant impacts on claim costs.
3. Legal system abuse and inflation related to social inflation are evolving and increasing at a rapid pace.

The level of volatility requires a whole new level of agility, creativity, and foresight to stay ahead.

How do you think the industry can better attract and retain the next generation of underwriting professionals?‍

We really need to rethink how we talk about the industry. Insurance doesn’t always have the most exciting reputation, but it’s an incredibly noble profession. We enable individuals, families, and businesses to get back on their feet and literally weather the storm, protecting their longevity. I think we need to highlight the purpose behind underwriting and the impact it has on society. 

Fresh thinking will help us solve industry problems.

I also think we have an opportunity to talk about all the exciting work we’re doing in the industry related to data, technology, and solutions. I think that fresh thinking from new folks coming into the industry without deep biases will help us develop completely new solutions for our customers, especially given the increase in consumer expectations.

Fresh thinking will help us solve industry problems.

If you could share one piece of advice with underwriters just starting out, what would it be?

I’d say take the time to learn the technical aspects of underwriting—things like policy language and manual rating. While I’m not suggesting people manually rate these days, understanding how it works and why it’s done is crucial. It builds a solid foundation for the challenges we face now, like volatility.

The best underwriters today are technically sound, curious, and ready to solve problems in creative ways. We can't just say no to everything. Instead, we need to find ways to say yes while managing risk. The key is combining technical knowledge with a problem-solving mindset to come up with new solutions that make a real difference for your customers.

What advice would you give to insurance organizations looking to implement AI or other technologies in their underwriting processes? What pitfalls should they avoid?

The biggest piece of advice I’d give is to focus on the business problems you’re trying to solve first. Far too often, organizations get excited about the shiny object of AI and rush to implement it without clearly understanding how it addresses their core business needs.

The biggest piece of advice I’d give is to focus on the business problems you’re trying to solve first.

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Start by identifying the problems you want to solve and the outcomes you want to achieve. Once you have that clarity, you can bring in the right technologies to match. Frame several use cases or business opportunities, and be clear about the potential benefits of addressing them.

Then, hold interactive sessions with your tech team, data team, and AI/ML teams to determine which solutions best align with those use cases. The key pitfall to avoid is chasing the “shiny object” just for the sake of it. Start with clear use cases and benefits, and work from there.

I’ve seen it work well when businesses lay out their needs first and work with data and analytics experts to figure out the best solutions. 

You’ve recently taken on an entrepreneurial role by starting your own consultancy. What inspired that decision?

‍After talking to a lot of carriers and insurtechs at recent conferences, I realized there was a need for someone with my experience to help them bridge the gap between technology and business opportunities. That’s when I decided to start NextGen Underwriting. It’s all about providing thought leadership, advisory, and consulting to underwriting teams.

With my background in underwriting and consulting, I feel well-equipped to help businesses implement underwriting strategies that drive profitability and growth. It’s a natural extension of the work I’ve been doing for years, but now I get to have a bigger impact on the industry as a whole.

Can you recommend a book that has been influential in your career or one you simply enjoy?  ‍

One book I highly recommend is StrengthsFinder by Tom Rath. It focuses on knowing your strengths and finding roles and opportunities that align with those strengths, which can lead to greater energy and success.

Another book that I find valuable is Quiet by Susan Cain, which explores the power of introverts and how to work with them.

Lastly, Never Eat Alone by Keith Ferrazzi is a fantastic book on networking, and it's something I live by as I love connecting people and maintaining a strong professional network.

How do you see the insurance underwriting landscape evolving this year?

The level of volatility we’re dealing with now means we need much better insights. I’m genuinely excited about what AI, advanced data sources, and data analytics can bring to the table.

The level of volatility we’re dealing with now means we need much better insights.

Here’s what stands out to me:

• New Data Sources: The availability and accuracy of data have evolved greatly, and new insurtechs and data providers are offering exciting perspectives on risk that we haven’t seen before.
• AI & ML: These tools give underwriters and analytics teams immediate access to insights about their book of business. This allows them to focus on high-value work, which is especially critical given resource scarcity in our industry.

Challenges remain around the rapidly changing risk landscape. The ultimate goal is to achieve profitable growth, which will require new insights and a greenfield approach that AI can help facilitate.