As fears mount over AI replacing jobs—or workers being outpaced by more AI-savvy peers—standing still has become a liability. For Winston Weinberg, the CEO of AI legal startup Harvey—now valued at $11 billion—that reality isn’t theoretical, it’s how he runs his company.
“You have to re-earn your position every six months; you need to re-earn your role at Harvey every six months,” Weinberg said on the latest episode of Fortune’s Term Sheet podcast. “It includes me, 100%.”
The mandate isn’t about churn for the sake of it—it’s about survival in an era where innovation is compounding quickly and falling behind can lead to dire consequences. That pressure is especially acute in Silicon Valley, where startups are racing not just against time, but against each other to build the defining AI companies of the next decade. For Harvey, that’s top of mind.
“If you don’t reinvent yourself as a company and as a leader, and whatever your role is at a company right now, fast enough, you will lose,” Weinberg added in the interview with Fortune’s Allie Garfinkle.
Weinberg, a lawyer by training, cofounded Harvey in 2022 alongside Gabriel Pereyra, a former Meta and Google DeepMind AI research scientist. In the company’s early days, the pair notably cold-emailed OpenAI CEO Sam Altman—an outreach that eventually helped them secure early access to GPT-4 and backing from the OpenAI Startup Fund. Harvey, which builds AI tools for law firms and in-house legal teams, has also attracted investment from Sequoia and Kleiner Perkins.
From the beginning, Weinberg said, the company survived depending on more than the technology—it required a culture that could move fast and adapt constantly: “The thing that I care the most about with our culture is decisiveness,” he said. “I think you have to basically build a company that has a culture of making decisions very quickly and being OK to make mistakes.”
Adaptability has been critical to Harvey’s $11 billion scale
That willingness to take risks and learn from them, Weinberg added, has been central to distinguishing Harvey from the influx of AI startups—and to helping it scale into a multi-billion-dollar business.
“The reality is, the folks that I have found that haven’t scaled—and when I myself think that I’m not scaling—it’s because I haven’t learned enough in the past couple of months,” he added.
So, when evaluating hires or emerging leaders, Weinberg looks for people who can grow quickly with the company—those who can go from managing no one to leading teams of 20, 50, or even 100.
“The main thing I look at is, can they make decisions, own that decision, and then pivot when they make a mistake?” he said. “Instead of penalizing the mistake, penalize not making the decision or not learning from that mistake going forward.”
A need for constant reinvention and learning is something other top executives have long echoed.
Accenture CEO Julie Sweet told Fortune last year that AI is creating a need to fundamentally change business processes.
“In order to capture the opportunity with AI, you really have to be willing to rewire your company,” Sweet said on the inaugural episode of the Fortune 500 Titans and Disruptors of Industry podcast. “Many times, when clients are saying, ’ We’re not getting a lot out of AI, it’s because they’re trying to apply it to how they operate today.”
Sweet stressed that adapting to AI isn’t a one-time shift; it’s an ongoing process.
“This isn’t about using AI on top of what you do today,” Sweet added. “If you’re not significantly changing the way you operate, then you’re not reinventing, and you’re not going to capture the value.”
At Amazon, CEO Andy Jassy has similarly emphasized the importance of continuous learning—especially through experimentation.
“We ask why, and why not, constantly,” Jassy wrote last year in a letter to shareholders. “It helps us deconstruct problems, get to root causes, understand blockers, and unlock doors that might have previously seemed impenetrable.”
