As fears grow that AI will replace jobs — or that workers will be overtaken by colleagues more familiar with AI — standing still has become a risk. For Winston Weinberg, CEO of AI legal startup Harvey — now valued at US$11 billion — this reality is not theoretical; This is how he runs the company.
“You have to win back your position every six months; you have to win back your role at Harvey every six months,” Weinberg said on the most recent episode of Fortune’s Term Sheet podcast. “That includes me, 100%.”
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The directive isn’t about turnover per se — it’s about survival in an era where innovation accumulates quickly and falling behind can have serious consequences.
This pressure is especially intense in Silicon Valley, where startups are racing not only against time but against each other to build the AI companies that will define the next decade. For Harvey, this is at the top of its priorities.
“If you don’t reinvent yourself as a company and as a leader, whatever your role in a company is now, fast enough, you’re going to lose,” Weinberg added in the Fortune interview with Allie Garfinkle.
Weinberg, a law graduate, co-founded Harvey in 2022 alongside Gabriel Pereyra, a former AI research scientist at Meta and Google DeepMind.
In the company’s early days, the pair sent an email out of the blue to OpenAI CEO Sam Altman — a move that ultimately helped secure early access to GPT-4 and support from the OpenAI Startup Fund.
Harvey, which develops AI tools for law firms and in-house legal departments, has also attracted investment from Sequoia and Kleiner Perkins.
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From the beginning, Weinberg said, the company survived by relying on more than just technology — it required a culture capable of moving quickly and constantly adapting: “The thing I care about most about our culture is the ability to decide,” he said. “I think you basically need to build a company with a culture of making decisions very quickly and being okay with making mistakes.”
Adaptability was crucial to reaching US$ 11 billion
That willingness to take risks and learn from them, Weinberg added, has been central to differentiating Harvey from the flood of AI startups — and to helping it grow into a multibillion-dollar business.
“The reality is that the people I’ve seen haven’t grown — and when I myself feel like I’m not evolving — it’s because I haven’t learned enough in the last few months,” he added.
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So when evaluating hires or rising 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 people.
“The main thing I look at is: can they make decisions, own that decision and then change direction when they make a mistake?”, he said. “Instead of punishing the mistake, punish not making the decision or not learning from that mistake from then on.”
The need for constant reinvention and learning is something other top executives have long championed.
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Accenture CEO Julie Sweet told Fortune last year that AI is creating the need to fundamentally change business processes.
“To take advantage of the opportunity with AI, you really have to be willing to restructure your company,” Sweet said on the inaugural episode of the Fortune 500 Titans and Disruptors of Industry podcast. “Often when customers say ‘we’re not getting much out of AI,’ it’s because they’re trying to apply it to how they operate today.”
Sweet emphasized that adapting to AI is not a one-off change; it is an ongoing process.
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“It’s not about using AI on top of what you do today,” he added. “If you’re not significantly changing the way you operate, then you’re not reinventing yourself — and you’re not going to capture value.”
At Amazon, CEO Andy Jassy has also emphasized the importance of continuous learning — especially through experimentation.
“We ask ‘why’ and ‘why not’ all the time,” Jassy wrote last year in a letter to shareholders. “It helps us deconstruct problems, get to the root causes, understand blockages and unlock doors that previously seemed impenetrable.”
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