Fortune 500 Firms Suffer 'Learned Helplessness' on AI, Futurist Amy Webb Says

Fortune 500 companies are pouring "enormous amounts of capital" into AI pilots "with no strategy ahead of them," futurist Amy Webb said at the Fortune AIQ Summit on Thursday, in conversation with Fortune's AI editor Jeremy Kahn.

Webb, founder and CEO of the consulting firm Future Today Strategy Group, did not mince words about where large enterprises stand. "Let's be fair, Fortune 500 companies are pretty late to the party on this," she said. "Artificial intelligence didn't just show up a couple of years ago."

The pattern she described is familiar and dysfunctional. Companies fund pilots, then argue with their security teams, and end up with orphaned projects that never deliver anything. Some executives hand the building of what becomes proprietary technology to third parties — and then get stuck. Employees grow frustrated and start building their own tools on the side.

Webb compared the state of corporate AI adoption to riding in a New York City cab and being handed a phone to type in an address, a pattern she estimated has held for about two years. Drivers have become so reliant on navigation tools, she said, that there is "a certain amount of learned helplessness" — just like some leaders in the current moment.

Her advice was not for companies to aim to be "AI native." The goal, she argued, is "being flexible," and companies must build mechanisms to make that possible. She said she has not yet seen large companies do so, even as many CEOs work to understand the technology.

Why the gains don't add up

Webb said part of the reason individual productivity gains fail to add up across a company is how firms define return on investment. Most apply AI straight to the bottom line. She contrasted that approach with Runway, the AI video company, whose strategy she considers a clear vision of the future that its tools help advance.

She told a story about a friend at a giant company she would not name. When the chief technology officer refused to approve a secure sandbox, the friend went directly to the CEO, built his own instance, secured access to a supercomputer and assembled a team. Webb said the group now plans to spend a couple hundred million dollars on AI tokens. She blamed the episode on a lack of "strong leadership and planning" and said many companies lead with "fear and FOMO."

Runway's counterexample

Michelle Kwon, Runway's chief operating officer, described a company built the opposite way. Runway was founded about nine years ago by three NYU graduates. It uses AI in "essentially every part of what we do," she said, and its entire staff writes code.

Since earlier this year, employees have built about 215 apps for an internal app store, including teams outside engineering. The company's newest product came out of that approach, she said. Runway announced a pilot for an autonomous ad agent the day before the panel; one worker built it in "a handful of weeks," and it raised ad output by more than 1,000% from a very small base. It is now being released publicly.

Runway still buys what is not central to the business, Kwon said. It will not build its own payment system or HR compliance software.

On productivity, Kwon drew a hard line. "Just because you are using AI, that is not a proxy for your productivity or you doing a good job at work," she said. AI should be a core part of how people work — as long as it is "responsible" and "doesn't create work for other people."

"It's not helpful if I receive a 100-slide deck," Kwon said. "What is someone asking me to do with that?" The same applies to chatbot output, which Runway sometimes receives: people "just copy and paste the output without having thought about: how do I synthesize this?" That, she said, just "isn't a productive use of anyone's time."

From the audience, Peloton's chief technology officer, Francis Shanahan, flagged the opposite problem. Employees are "inundated now because they can literally build anything," he said, and he is finding "burnout to be more and more of an issue."

Kwon responded that Runway makes a point to "celebrate the wins" and "shout people out." The company gives everyone the same day off, not tied to a holiday, because with summer Fridays it is hard to track who takes a half day and who takes a full one. When Kahn joked that AI agents could keep working on those days, Kwon replied: "They can work tirelessly."

Risk and liability

Matt Maher, founder of M7 Innovations and a consortium partner with MIT Media Lab, asked who is liable when an AI agent breaches a contract or causes other harm. Webb answered with a story of her own: a coding project she once built spammed 1,000 people after she put it in a live environment with a loop in it. Such failures, she said, are ordinary human errors, not AI "waking up." Executives, she argued, must "stop anthropomorphizing" AI.

Webb added that security and risk officers should say "tell me more" before they say no, and that leaders should give them leeway. She also warned that a wave of connected devices — glasses and charms that listen — will arrive over the next 18 months with little planning behind them.

Asked about boards using AI, Webb said her firm has used it for a decade, but it is useless if directors do not understand what the data show. She compared the situation to her own cycling sensors. "You can't disassociate from what's happening," she said, "or you are liable."

Webb's message sets a clear bar for the next 18 months: companies that treat AI as a bolt-on to the bottom line will keep producing orphaned pilots, while those that build flexibility into how people actually work — as Runway claims to have done — will pull ahead.