Eligible

Caitlin Gleason's path to healthcare started with a restaurant job at 13 and a sales job at 20 selling for a business directory. She left that company because it would not improve a product that she could see was capable of much more. That frustration shaped the rest of her career. After years of acting, reading and odd jobs, she took a sales role at Dr. Crono in New York in 2010 on one condition: that she could be involved in the product.

At Dr. Crono she saw a trend that most people in the industry missed. Health plans were moving costs to patients through deductibles and co-insurance, but the billing systems focused on insurers paying providers. Nobody was building technology for patients paying providers. Caitlin has described this as crystal clear from day one.

She left Dr. Crono with about $5,000 in savings and a credit line of roughly $25,000. She paid it off before interest kicked in. She called this her investment in herself. She had no fallback, and that urgency pushed her to commit. She began by reading the HIPAA-related X12 EDI eligibility specification at her kitchen table, and she found a non-technical founder's advantage in focusing on user requirements rather than implementation.

Her first prototype was an iPhone app that showed patients exactly where they stood in their deductible. Working with an aggregator, she realized that an API built on JSON would be simpler than parsing the old formats. That decision created value for partners, who later told her the approach cut integration time sharply.

Early on she went door to door and found a provider in Mountain View willing to test the idea. She also partnered with an aggregator that had insurance connections. She later retired both the app and the aggregator so Eligible could build its own connections. Early customers paid a few thousand dollars a month. A major driver of growth was posting on Hacker News, which brought in many customers because the product was an integration that developers could adopt.

Compliance and security were the heavy costs. She described spending most of the company's investment over five years automating certifications, which slowed the team but also created a moat that competitors would have to pay too. Caitlin has said that the biggest mistake was not the early history but how she handled scaling, when she was too aggressive with a growing team across several countries. Her company later grew 8.4x, reached profitability, and then raised significant capital.

Eligible now processes billions of dollars in healthcare expenditures per month, roughly 20 million transactions, and has touched over 100,000 providers daily. Caitlin says category creation let the company raise prices sharply, with one pilot priced at about $26k per month against a previous payment of a few hundred dollars.