Harvey CEO Winston Weinberg Is Fixing Law’s ‘Broken Apprentice System’

Winston Weinberg, featured on this year’s A.I. Power Index, is a lawyer turned tech entrepreneur who is redefining the practice of law with Harvey, his A.I.-powered platform for legal and professional services. Since launching in 2022, Harvey has reached $100 million in ARR in just three years, with weekly average users quadrupling over the past year. The platform now serves clients in 53 countries and has forged strategic partnerships with industry leaders such as LexisNexis, PwC and Microsoft Azure.

Weinberg emphasizes that Harvey is transforming the day-to-day work of lawyers at every level. “Most forward-thinking firms know A.I. is going to change their business, it’s just a question of how much and when,” he tells Observer.

What’s one assumption about A.I. that you think is dead wrong? 

That it creates a net negative impact on the current work experience. Harvey serves legal and professional services, and right now, if you’re a junior lawyer or an associate in financial services, you’re doing a lot of work that doesn’t reflect your training and what you thought the role would entail. A.I. changes that and ideally makes the work you do as a human more meaningful.

If you had to pick one moment in the last year when you thought, ‘Oh shit, this changes everything,’ about A.I., what was it?

The release of reasoning models.

What’s something about A.I. development that keeps you up at night that most people aren’t talking about?

I don’t think folks are spending enough time thinking about the future of training young professionals.

You’ve pioneered an ‘expand and collapse’ product philosophy where Harvey builds specific, detailed workflows for complex tasks and then integrates them into unified, simple interfaces. With Harvey now reaching $100 million in ARR and serving over 500 customers, how do you balance the tension between creating highly specialized A.I. capabilities for elite law firms versus building accessible tools that can scale across the entire legal market—and what does this approach reveal about the future architecture of professional A.I. systems? 

If you’re building A.I. in a vertical right now, it’s important to design your system as a platform. In order to get the best ROI, you need a product that both (1) can be used generally across a profession in a creative way by the user and (2) allow the user to “click” to get instant value in a specialized use case. Luckily, the models are getting better at tool use and general orchestration, so you can use those capabilities to get the best of both worlds.

PwC partners report that junior lawyers would ‘riot’ if Harvey were taken away because it allows them to focus on qualitative rather than tedious work. Yet, law firms traditionally make money from billable hours. You believe A.I. will help fix ‘an apprentice system that’s long been broken’ in professional services. How are you navigating the fundamental economic disruption Harvey creates for law firms, and what new business models do you envision emerging when A.I. can reduce legal processes from weeks to minutes? 

The short answer is thoughtfully. Most forward-thinking firms know A.I. is going to change their business, it’s just a question of how much and when. You’re already seeing firms experiment with project-based work and fees, and you’re seeing significant client demand for firms to use A.I. in a manner that benefits them. As a result, the role Harvey can

play is simply to make the best product possible that solves core problems for lawyers and to make it as easy as possible for them to do so. By serving both firms and enterprises, we are laying the foundation to help them run their own transformation playbooks, but also to collaborate together long-term in a manner that makes law more efficient and effective for everyone.

Your strategy of targeting prestigious, conservative clients like Allen & Overy and PwC first was designed to build credibility, and you maintain that only 18 percent of Harvey’s workforce are lawyers. Yet, you believe attorney-employees are “essential to achieve Harvey’s goal of ‘partnering’ with the industry.” Given that some older partners may be using Harvey as their first A.I. product, how do you design both technology and go-to-market strategies that earn trust from an industry where prestige and trust are paramount, and what lessons does this hold for A.I. adoption in other traditional sectors?

I think the conventional wisdom is to pick the easiest customers and build momentum, and we did just the opposite. We picked the hardest customers to win over and the highest degree of difficulty on enterprise readiness, privacy and security, and I think that was very much by design. You have to start with enterprise trust, and everything else follows. With regard to partners, 20 percent of all of our users are partners, so it’s not just junior associates benefiting from Harvey in daily work. In the firms that are more successful, partners are helping lead the transformation work.

You argue that A.I. agents will “rewire the leverage pyramid” and enable lawyers to “return to their core role as strategic advisors while automating routine work.” You’ve also stated that professionals’ options to do that in the next decade are the best it will ever be because “you will make more impact than you ever will have the chance to in your life.” As someone who left Big Law after just one year to build Harvey, what do you see as the most profound ways A.I. will reshape professional identity and career trajectories—not just in law, but across knowledge work—and how should educational institutions and firms prepare the next generation for this transformation? 

Law at its very best is a strong apprenticeship model, but that’s gotten lost in a lot of the busy work that has come along with scaling the profession. I think many lawyers believe there’s a better way, and part of Harvey’s ambition is to help free up lawyers’ time to focus on the most impactful work. Less busy work, more impact. While we hope our product helps lawyers save time, we also want to be more proactive in shaping the future of law, which is why we just launched our Law School partnerships program. That program will bring A.I. fluency and the Harvey platform to students and professors alike, and our hope is that the partnerships will have a meaningful impact on sharing the future of knowledge work alongside these institutions and their faculty members.