Oscar Health’s New CEO Has a Tough Job—but Lyft’s New CEO Has It Worse

Mark Bertolini must be feeling pretty good. Since he was named the new CEO of Oscar Health on Tuesday, Oscar’s long-suffering stock has bounced 78%. OK, skeptics will point out that bounce was off a very low base—the stock was at $3.59 on Monday. And even after the rally, Oscar stock is still down 84% from its initial public offering price. But any stock lift is better than the alternative, which is what greeted Lyft’s new CEO, David Risher. Since Monday afternoon, when his appointment was announced, Lyft’s stock—which has been in the toilet so long it’s gotten lost in the plumbing—has fallen 6%. 

What to make of the diverging reactions? Both executives are taking the reins of long-struggling companies from founder-CEOs, Mario Schlosser at Oscar and Logan Green at Lyft. But investors seem to be more hopeful that Oscar’s new chief can make something of the tech-driven health insurer than they are that Lyft’s new CEO can turn around the ride-hailing firm. That’s presumably partly because Bertolini is a health insurance veteran who previously ran Aetna. And he’s operating in an industry that has demonstrated profitability is possible.