Okta’s President and COO says companies are in denial about the hardest part of the AI revolution: redesigning work itself

Eric Kelleher has a problem that no amount of AI can solve for him.

The President and COO of Okta has agents on his team. He’s named them—Leo, Sloan, Hank, Walker—and they show up in business reviews alongside his human staff. He’s personally booked a flight to Bangalore and spent the entire trip standing up an open-source agent on a separate machine, a deliberate act of immersion he then assigned to every member of his leadership team. “That flight to me was transformative in how I recognized what the capabilities of this technology are,” he told a roomful of top operations executives at the COO Summit this week.

And yet, he added, the hardest part isn’t the technology. It’s the managers.

“We have trained every manager in the world to think about one thing and that is: what’s their headcount,” Kelleher said. “Our managers have spent decades learning how to think about headcounts and payroll.” The shift he’s advocating for at Okta — getting managers to budget explicitly for both human labor and digital labor, to think about work charts that include AI agents as genuine colleagues—is, he said, “a much harder problem than getting people to experiment with Claude Code.”

“One of the things I’m really advocating for within Okta is to get our managers thinking about how to design work to include human workers and digital ...