The Singularity Is Coming for the Corner Office

The New Executive Team

Douglass’s AI fleet has become an extension of his decision-making apparatus. He built Slacker monitors his Slack conversations and suggests action items, eliminating the mental overhead of tracking his to-do list. Salesy McSalesforce handles data analysis and quality assurance. Douglass uses at least three or four agents every day, with plans to build more by year’s end.

The impact goes beyond efficiency. “I delegate a lot less than I used to because all of a sudden, I can do these tasks so much faster,” Douglass said. The ability to handle more himself — from document review to “vibecoding” small applications through natural language prompts — keeps him closer to the business’s operational reality.

KC Estenson, CEO of GoNoodle, a kids’ health and wellness platform, takes a different approach. Rather than building task-specific agents, he uses Anthropic’s Claude to create digital doppelgangers of the people in his orbit. He has constructed personas representing employees, customers and stakeholders, then uses them to pressure-test ideas before bringing them to the real world.

The technique paid off before a recent board meeting. Estenson workshopped his presentation with a persona modeled on a particularly demanding private equity board member. The AI suggested cutting the meeting from three hours to 90 minutes. When Estenson made the change, the real board member — the one he’d modeled the persona on — told him it was the best meeting they’d had.

“It’s like having one of the best consultants you could ever have, who knows your business inside and out, and who never gets tired, sitting at your fingertips,” Estenson said. He even created a Brené Brown persona, prompting Claude to replicate the author’s thinking when he needs leadership advice.

Douglass and Estenson’s approaches converge on a common theme: AI is allowing CEOs to reclaim work they’d previously been forced to delegate.

Estenson pointed out that a CEO might rely on a chief of staff, a head of communications and an investor relations liaison to help shape decisions and messaging. Now, AI can assist leaders to do the same work “faster, in private and on-the-fly, in the margins of their day.” As a result, “I’ve become a much more effective CEO,” Estenson said.

Preparing for the Singularity

Douglass has found his rhythm with AI agents, but he knows this is just the beginning. He’s watching for something bigger: the moment when AI can handle not just his bug reports, but strategic decisions that currently require his judgment. When OpenAI released GPT-5 and it failed to deliver the massive leap many anticipated, he felt relief rather than disappointment. It gave him breathing room to prepare for the so-called singularity, when AI will theoretically be able to execute the core functions of leadership itself. But that breathing room is temporary.

“I think that’s the next wave: making them easier to use, not necessarily making them more powerful. But I do think it will happen. It is something I watch constantly,” Douglass said. Every major release triggers the same internal calculation: How big is this leap? To stay prepared, he believes CEOs need to understand AI’s building blocks well enough to make their own judgments, rather than relying entirely on advisers.

Estenson thinks about the post-singularity CEO often enough that he wrote a book on it. In “The Augmented Leader” he argues that as AI masters functions such as finance, data analysis, research and strategy, the executives who thrive will be those who can articulate bold visions, rather than manage daily operations. CEOs “who can use their imagination to peer around corners to make bets on the future, to strongly articulate a vision for their companies — AI will help those types of leaders in a compounding way,” said Estenson.

The Cognitive Trade-Off

Executives like Estenson and Douglass are cataloging what they stand to gain from AI. What remains less clear is what they might lose in the process.

Several studies have documented a troubling pattern: overreliance on AI leads people to engage in less critical thinking, with measurable deterioration in cognitive abilities and work processes.

“Convenience is silently reshaping our intellectual architecture,” wrote researcher Timothy Cook in Psychology Today. “Why do we so readily surrender our cognitive autonomy? Perhaps because delegation feels like empowerment. Each time AI completes a task we once performed manually, we experience a momentary efficiency gain.”

The efficiency Douglass and Estenson describe is real. But if current AI raises questions about which skills executives might be trading away, superintelligent AI would make those questions existential. In a world where AI can execute strategy and operations flawlessly, the only leadership skills that matter are the ones machines can’t replicate.

For now, Douglass keeps building his fleet of agents, watching for the next breakthrough. Estenson keeps creating personas and refining his vision of augmented leadership. Both are making the same bet: that the future belongs to executives who know when to think for themselves.