How Olive pivoted 27 times on its way to a $4 billion valuation

Olive is a homegrown Columbus, Ohio unicorn; hear from the CEO and lead investor how the company was founded and grew into an industry leader.

Sean Lane co-founded Olive in 2012, and signed on Chris Olsen from Drive Capital as the company’s first investors. Now, nearly 10 years later, Olive has raised $856.3 million on its way to being a driving force in using artificial intelligence in the healthcare industry. But the company’s path to success wasn’t a straight line. As CEO Sean Lane explains on this special TechCrunch Live event, the company pivoted 27 times before finding its current product market fit.

Lane explains the strategy behind changing a company’s direction and the emotional toil it takes on everyone involved — from employees to executives to the investors.


Missed the event? Watch the rest of the panels here.

Techcrunch event

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Join 10k+ tech and VC leaders for growth and connections at Disrupt 2025

Netflix, Box, a16z, ElevenLabs, Wayve, Hugging Face, Elad Gil, Vinod Khosla — just some of the 250+ heavy hitters leading 200+ sessions designed to deliver the insights that fuel startup growth and sharpen your edge. Don’t miss a chance to learn from the top voices in tech. Grab your ticket before doors open to save up to $444.

San Francisco | October 27-29, 2025

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