The Future of Insurance Podcast - Kyle Nakatsuji
CEO & Co-Founder, Clearcover
Season 1, Episode 7, June 8th, 2021
Guest Bio
Kyle is the co-founder and CEO of Clearcover, the smarter car insurance company. Under Kyle’s leadership, Clearcover has raised more than $300 million to date and currently operates in 15 states with more on the way.
Before founding Clearcover, Kyle was a founding member of American Family Ventures where he was responsible for sourcing, evaluating and structuring over 50 equity and debt venture capital investments in nationally-based tech startups.
Prior to this role, Kyle was a corporate attorney focused on emerging company business matters at AlphaTech Counsel. Kyle has a law degree and an MBA from the University of Wisconsin.
Highlights from the Show
- Kyle Nakatsuji helped start the venture team at American Family in early days in InsurTech and CVC in the industry
- To be successful as an InsurTech company requires a hundred things that need to be done right to succeed, with a fundamental need for an advantaged cost structure and enabling technology at the core
- Customer want to come away from interacting with you feeling confident in the choice they made to do so, which takes four ingredients
- Transparency
- Convenience
- Low Prices
- Superior Value
- They use their fundamentally advantaged cost structure enabled by their technology to deliver a truly customer-centric insurance organization that is differentiated in each of those four ingredients
- For example, they are decidedly multi-channel to transact where customers want to
- These four ingredients together create a virtuous cycle where they can differentiate more and create more value as they deliver
- For example, giving convenient, transparent claims service quickly means they are lowering their prices, which enhances the value to customers and allows them to lower prices (or provide other valuable things to customers)
- Embedded Insurance is a major piece of their story, but it isn’t the whole story
- Being a startup means you have the advantage of a blank piece of paper, which means you don’t need to rationalize your actions the same way that an existing carrier might have to
- Running a technology company in insurance means effectively running two kinds of companies under one roof at the same time, with world class technology talent and insurance talent, which are very different
- The essence of startups is risk, you’re supposed to be able to fall off the high wire and die. If that wasn’t the case, everyone would do these things and startups wouldn’t exist
- Kyle sees three waves of InsurTech
- The first wave are growing up now, and the next companies will have to solve different problems
- The second wave is the solution providers helping the industry overall
- The third wave are solving for white spaces that are still developing and unclear that are hard to even imagine right now
- The market is so big that even the edges of it are still huge opportunities.
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Thank you to our sponsor
Special thanks to Medallia for sponsoring this episode.


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