From Interview: Oscar Health CEO Mark Bertolini · · Asymmetric Investing by Travis Hoium
“We're a tech-first insurance company. We're digitally native. We have one platform. It's the first new platform in health insurance since 1972. We have one data set, so one version of the truth. So, for us implementing AI is a very simple thing. We have over 40 large language models on the back end of our business. And we have uh now three agentic AI bots on the front. Um where we interact with our members.”
On , Mark Bertolini, Former Chairman & Chief Executive Officer at AETNA INC, spoke about artificial intelligence during Interview: Oscar Health CEO Mark Bertolini on Asymmetric Investing by Travis Hoium.
Mark Bertolini, CEO of Oscar Health, has been discussing the company's technology-driven approach to health insurance and advocating for changes to the U.S. healthcare system. In a May 2026 interview, he described Oscar as a "tech-first insurance company" that is "digitally native" with a single platform and data set, and stated that the company uses over 40 large language models and three agentic AI bots. He said Oscar operates solely in the ACA marketplace, covering about 3 million lives across 21 states, and noted that the company has reduced operating costs by a billion dollars while growing from 750,000 to 3.5 million members with the same number of employees. Bertolini argued that Americans are "fed up" with current coverage and that the shift from defined benefit to defined contribution models, such as ICHRA, will happen faster than the transition from pensions to 401(k)s. In a February 2026 conversation, Bertolini criticized the current health insurance model, saying it "conflates financing with investment" and that healthcare is the most expensive household line item with no consumer shopping ability. He proposed separating financing from investment through Roth IRA-like HSA accounts, allowing individuals to buy networks and plan designs that fit their circumstances. Bertolini also discussed his personal experience as a caregiver for his son, who was diagnosed with terminal cancer, and said this informed his perspective. He highlighted a new platform called Lucie, which aims to create a shopping experience for healthcare, and noted that six states have passed legislation to support this model.