care-shift-jared-article-november-2026
November 11, 2026

New Episode of Care Shift with Jared Kaplan

This article was originally published on the Care Shift Substack: https://careshift.substack.com/p/new-episode-of-care-shift-with-jared.

Jared Kaplan is the Co-Founder and CEO of Indigo, an AI-powered medical malpractice insurance platform that recently raised $50 million in Series B funding in January 2026, led by Rubicon Founders.

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Main Takeaways

1.The most boring industries are the best places to innovate

Jared looks for old-school industries that lack strong product and data science talent and draw little private capital. Medical malpractice fit perfectly: a $13 billion market dominated by a handful of incumbents with almost no technology.

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2.Coming from outside the industry is an advantage, if you pair it with insiders

Not having a healthcare background meant Jared had no biases about how things “should” be done. He balances that by surrounding himself with 20 to 30 year industry veterans who tell him which of his ideas won’t work.

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3.Automate only as fast as your confidence allows

Indigo started with humans in every step and slowly reduced their time as the models proved accurate, reaching about 40% autonomous underwriting today. With million-dollar policies on the line, Jared would rather move carefully than blow up

the book chasing growth.

4.Better data beats the industry’s old pricing model

Incumbents price doctors on roughly four data points, while Indigo’s Lux platform pulls 1,500 attributes with no application required. That lets Indigo quote in under a day and identify the 20% of physicians likely to drive 60% of next year’s claims.

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5.Tech doesn’t replace trust in a people business

On launch day, Indigo got exactly one submission, which taught Jared that brokers and physicians need to believe you’re credible and here to stay. Indigo now invests heavily in its BD team and broker relationships, and often wins customers on the second or third time they hear the name.

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6.Raise what you need, not everything you can

Indigo’s Series B was oversubscribed, but Jared capped it because too much capital leads to bad decisions and dilution hurts every employee owner. He prefers setting realistic expectations and beating them over chasing short-term growth.

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7.Culture is how your team feels on Sunday night

Indigo defines culture as whether employees are excited to come to work on Monday morning. Jared believes losing your best people is the fastest way to kill a business, so everything they do centers on recruiting top talent and keeping it.

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Links to the episode

Youtube

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Spotify

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Apple Podcasts

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Image from original article.

Further Reading