Hello and welcome to Modern CEO! I’m Stephanie Mehta, CEO and chief content officer of Mansueto Ventures. Each week this newsletter explores inclusive approaches to leadership drawn from conversations with executives and entrepreneurs, and from the pages of Inc. and Fast Company. If you received this newsletter from a friend, you can sign up to get it yourself every Monday morning.
Mark Bertolini is no stranger to scale. When he was CEO of Aetna, he helped orchestrate the health insurer’s 2018 sale to CVS Health for $69 billion. In 2022, he became co-CEO of the hedge fund Bridgewater, which had $168 billion in assets under management at the time. He’s currently chairman of the board of Verizon, which boasts a $177 billion market capitalization.
Bertolini also leads Oscar Health, which provides insurance to individuals, families, employers, and employees through the individual market. Oscar, which last year reported revenue of $11.7 billion and whose market value is $8.5 billion, is small compared with Bertolini’s other stops. But Bertolini, who joined as CEO in 2023, says he accepted the job because he saw an opportunity to transform a flawed system. “We have a shot at actually figuring out how to make healthcare work for all Americans,” he says. “That’s why I’m there.”
Tailored, tech-first networks
Oscar Health, founded in 2012 by Joshua Kushner, Kevin Nazemi, and Mario Schlosser, builds provider networks tailored to local communities rather than tapping the broad commercial networks used by legacy carriers. Bertolini says this strategy, coupled with a technology-first approach, delivers better cost control and customer care.
Last year, the company introduced Oswell, a personal AI health assistant powered by OpenAI models. Oswell can help patients with tasks such as tracking medications and appointments and answering questions about lab results. Oscar clinicians can also use the tool to review treatment options. Earlier this year, Oscar launched Lucie Health Marketplace, a platform Bertolini has described as “Airbnb for healthcare.”
Since Bertolini’s arrival, Oscar has increased its membership from about 1 million to about 3 million. The company reported a 53% increase in first-quarter revenue to $4.6 billion and affirmed that it would be profitable in 2026, reversing a loss in 2025. The stock price has more than doubled this year despite the expiration of Affordable Care Act subsidies. The company says it responded to the sunsetting of the tax credits by launching new low-cost products during open enrollment 2026 for consumers losing enhanced premium tax credits.
Hedging against unexpected bumps
Bertolini marries a startup CEO’s idealism with a corporate veteran’s leadership acumen. He professes that curiosity is important to solve big challenges like healthcare affordability, and he reinforces and rewards inquisitiveness through processes and norms. The company builds operating and strategic plans factoring in risks, or what Bertolini calls “things that go bump in the night.” And when things do go bump in the night, Bertolini says, leaders should “deliver bad news early and personally so we can get on [solving] it.”
Indeed, Bertolini believes success can lead to complacency. At monthly operational meetings with leadership, he reviews key numbers and metrics to understand market conditions and how Oscar should adjust.
Finally, he urges everyone in the company to assume positive intent in others’ actions, including those of competitors and regulators. He believes this openness is another opportunity for curiosity. “We should call on ourselves and ask, ‘What is it that that person’s trying to teach me that I don’t yet understand?’” he says.
How curiosity fuels a growth mindset
Bertolini’s codification of curiosity feels reminiscent of Satya Nadella’s growth mindset work at Microsoft or of Amazon’s leadership principles. Does your company value curiosity, and how do you reinforce it? Send your insights to me at stephaniemehta@mansueto.com, and we’ll publish some of the best ideas in a future newsletter.
Read more: curiosity
- Why coming in second may be the best thing that ever happened to you
- Embracing this mindset actually rewires your brain
- AI is making answers cheap. Curiosity is priceless
