How Harvey’s 31-Year-Old CEO Winston Weinberg Is Reshaping Big Law with A.I.

Winston Weinberg understands what junior associates at law firms need because he was once one of them. In 2022, the then 27-year-old was working at O’Melveny & Meyers when he began experimenting with OpenAI models alongside his roommate, Gabe Pereyra, then a research scientist at Meta. After realizing A.I. could streamline inefficiencies in the legal sector, the two cofounded Harvey, a startup built for lawyers.

Since then, Harvey’s tools have become a must-have for Big Law, used by more than half of the AMLaw 100 firms. Clients include powerhouse firms like Paul, Weiss, as well as in-house legal teams at PwC and KKR. Three years in, Harvey serves more than 1,000 customers across 6o countries. “Demand broadly for A.I. for legal is at an all-time high,” Weinberg told Observer over email.

Silicon Valley has taken notice, too. After Weinberg cold-emailed the OpenAI Startup Fund, it became Harvey’s first institutional investor. The company was most recently valued at $8 billion following a $160 million round in 2025—a year when it raised capital three times—and closed with more than $190 million in annual recurring revenue.

Harvey has continued to expand through a partnership with LexisNexis, integrating its legal content and citations, and by working with leading law schools at Stanford, NYU and UCLA to bring A.I. into legal education. Last month, it even came full circle, partnering with Suits actor Gabriel Macht—the man behind Harvey Specter, the character that inspired the startup’s name—in what Weinberg called a “meaningful nod” to its origins.

But Harvey isn’t resting easy. It faces fresh competition from rising players like Sweden’s Legora, valued at $5.5 billion, and established entrants such as Thomson Reuters’ CoCounsel. Major A.I. developers like OpenAI, Anthropic and Google also loom large as they expand into enterprise applications.

Observer caught up with Weinberg to discuss what’s next for Harvey as it scales globally, navigates competition and workforce shifts, and charges ahead on its mission to bridge law and technology.

The following interview has been edited for length and clarity.

How did you first come up with the idea of Harvey?

Gabe and I started experimenting with early GPT-3 and quickly saw its potential for legal work. I was a junior associate at O’Melveny & Myers at the time, and after running a simple test with real legal questions and blind attorney reviews, it was clear the technology could fundamentally change how lawyers work. We decided to go all in and cold-emailed Sam Altman at OpenAI. That conversation led to our first backing and the start of Harvey.

Is it true that Harvey takes its name from Suits?

One of the things people forget about A.I. adoption is that getting human beings to change the way they work is notably hard. When Gabe and I first started testing our product with users, we noticed that they spoke with us in a normal human voice, but when they went to prompt, they got very rigid and formal. Their prompts were far worse than the clear directions they would give a junior associate, so we very intentionally tried out the difference when people were speaking to a human name versus a formal product name, and the results were staggering.

Harvey’s naming has three components: 1) a human name given the above behaviors we observed with lawyers, 2) inspiration from a famous lawyer who inspired many people to pursue law, and 3) it sounds like “Harvard,” which people laugh at, but in this case, matters as we think about building a brand that is credible and trusted with legal teams globally.

How did you initially get the attention of law firms, and what have been some of the biggest challenges in enabling A.I. adoption across the legal sector?

Early on, it was about finding the futurists, like David Wakeling at A&O Shearman, Claudia Junker at Deutsche Telekom and Bivek Sharma at PwC, and meeting people who knew A.I. would have an impact on legal. Then it was about really listening to what mattered to the world’s top legal teams, which is why we spent so much time early on on security and governance as top priorities. We also got a lot of “nos”—it’s easy to look back now at the traction and think it was a walk in the park, but the reality is we were lucky enough to meet some change agents early and build their trust, and the industry as a whole has changed profoundly in a very short time with regard to attitudes towards A.I.

How many of your clients are law firms versus corporate legal teams? Are you hoping to change that ratio going forward?

We have a strong mix of both—law firms were where we got our start, so they remain the majority of our customer base, but the in-house business is growing rapidly. In the last few weeks alone, we’ve announced working with Eversheds Sutherland, Corrs, Stinston, Kromann, a global expansion with DLA Piper, and a renewal with Vinge on the law firm side, and HSBC on the in-house side.

Our Shared Spaces product enables collaboration between law firms and companies, and for teams within companies, in a manner that hasn’t been possible before. So our goal is actually not a ratio of firms and corporates per se, but rather a measure of how many legal teams are collaborating within Harvey on any given day–that’s the metric I value most.

What’s next for Harvey? What are you most excited about for 2026?

So much–we just hired our first chief product officer, Anique Drumright, and our vice president of design, Christina Nguyen White, and I’m thrilled to see the folks they hire and the impact they will have on our customer experience. We also announced multiple office openings in Singapore, Dallas, Dublin, Paris and Bangalore in addition to our existing locations in Sydney, San Francisco, New York, London, and Toronto. We hosted our first-ever owned event, the Harvey Forum in London, and will be hosting our next Harvey Forum in New York soon, so a lot to look forward to in the near future.

How do you think about A.I.’s impact on white-collar professions, especially when it comes to junior roles?

It’s one of my core beliefs that A.I. will transform the profession of law, but when done well, it will create more opportunities for mentorship and for the kind of law careers many people (myself included) imagined when they signed up for law school. You’re already starting to see this—the best lawyers charge for high-level, deal-making or breaking strategy work and are compensated well for it. I don’t think that will change. What will change are all the repetitive redline tasks, where A.I. can transform many existing workflows.

But your point is well taken which is that the industry as a whole needs to continue investing in junior talent, which is why we at Harvey are doing two things: 1) building out our own internship and early career program so we lead from the front on this, and 2) partnering so deeply with law schools in the U.S., UK, Spain, and Australia to help them prepare alongside school faculty for the future of law including A.I. Our goal is to work with the industry to be a thoughtful part of this solution.

How will you continue to differentiate Harvey from competitors? What’s to stop major A.I. players, like OpenAI, Anthropic and Google, from dominating the legal sector? 

We have a ton of respect for each of those organizations, and they are all key partners because Harvey’s platform includes their respective models. We’ve said for many months, both publicly and privately, that long-term, the model companies are the most likely competitors in vertical A.I. That doesn’t change our approach, but it does increase our urgency to focus on differentiated components, like security, governance, collaboration, memory and integrations, to ensure we remain the solution of choice for law firms and in-house teams and legal A.I. for their internal use and to collaborate internally and externally.