How to pivot your startup, save cash and maintain trust with investors and customers

A few years ago, founder Sean Lane thought he'd achieved product-market fit.

Speaking to attendees at TechCrunch's Early Stage virtual event, Lane said Queue, a secure digital check-in tablet for hospital waiting rooms that reduced wait times by uniting and correcting electronic medical records, was selling like hotcakes." But once Lane realized it would only ever address one piece of a much bigger market opportunity, he sold off the product, laid off two-thirds of the people affiliated with it and redirected the employees who were left.

Lane explained that what he really wanted to build is what his company - since renamed Olive - has now become, a robotic process automation (RPA) company that takes on hospital workers' most tedious tasks so nurses and physicians can spend more time with patients.

Customers seem to like it. According to Lane, more than 600 hospitals use the service to assist employees with tasks like prior authorizations and patient verifications.

Investors clearly approve of what Olive is selling, too: Last year, the company raised three rounds of funding totaling roughly $380 million and valuing the company at $1.5 billion. According to Crunchbase, it's raised a total of $456 million altogether.

In fact, VCs think so much of Lane that in February, they invested $50 million in another company that Lane runs simultaneously called Circulo, a startup that describes itself as building the Medicaid insurance company of the future."

Still, the path from point A to B was painful, and it might not have happened if Lane didn't have a few things going for him, including a deeply personal reason to build something that could have greater impact on the U.S. healthcare system.