The Future of Insurance Podcast - Chris Cheatham
VP of Product, Insurance Intelligence, Bold Penguin
Season 1, Episode 5, May 25th, 2021
Guest Bio
Chris Cheatham is the Vice President of Product at Bold Penguin, where he helps lead the Insurance Intelligence division. He has been in this position since October 2020. Bold Penguin is the world’s largest commercial insurance exchange, where agents can quote and bind small businesses in record time. In 2020, Bold Penguin was responsible for over 1 million quote starts.
Chris sits at the intersection of product and marketing, where he provides feedback and messaging between insurance professionals and Bold Penguin product development. In January 2021, Chris launched the Bold Penguin Agent Council to provide direct feedback between technical leadership and agents utilizing the Bold Penguin Terminal to quote and bind.
Prior to Bold Penguin, Chris was the Co-Founder and CEO of RiskGenius, where he created insurance policy review software that has processed over a million insurance clauses with the aid of artificial intelligence. Bold Penguin acquired RiskGenius in October 2020. Before launching his technology business, Chris was an insurance attorney in Washington, D.C. for five years.
Chris holds a bachelor’s degree in political science from the University of Kansas and a juris doctorate from the University of Texas at Austin.
Highlights from the Show
- Chris was struck by the need to understand what was and wasn’t covered and what the language in a policy meant from his work as an attorney
- He sought to bring out what the most common, lowest denominator was across competing policies
- That was the intention of RiskGenius, and he raised $13 million and hired 30 people along the way to understand insurance coverage by using computers
- They needed to figure out what the problem was that they needed to solve
- They tried to do it all, but Chris would have started smaller and put on blinders if he was doing it again because of all the ideas coming at you
- Budget for his customer vanished for a year, and you can’t survive that wait as a startup
- QBE came to him, having to understand all the wordings and coverage they had through the various acquisitions they had made to rationalize their policy forms
- Then the shifting focus on small business started to emerge, with more and more online quoting and binding activity
- That focus is why Bold Penguin has been so successful, and adding RiskGenius to their platform made sense in helping to identify the right coverage or help people select the right coverage
- One major hold back for the industry is carrier APIs, as many are too complex, limiting or hard to connect with
- It all comes back to the pipes (connecting different players in the ecosystem)
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Thank you to our sponsor
Special thanks to Medallia for sponsoring this episode.


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