Why I Left Big Law For Legal Tech – Artificial Lawyer

By Darpit Vadodaria, August.

I spent 7.5 years as an M&A lawyer at Willkie, Paul Weiss, and Milbank, focusing on private equity, public M&A and activism defense. Unlike many Big Law associates, I loved the practice of law and really enjoyed advising companies through complex, high-stakes transactions that could reshape their businesses and fuel their growth.

However, what frustrated me about Big Law was the inefficiencies that kept lawyers from focusing on the high-value parts of their practice. Obsessed with efficiency, I turned to legal technology as the solution.

At every firm I worked at, I served on the technology committee, shaping decisions on which legal tech tools to procure. That experience revealed a hard truth: most legal tech vendors don’t truly understand how lawyers work, the time pressures we face or what different segments of stakeholders across a firm – KM teams, juniors, mids, seniors, partners – actually need.

Why I Left Big Law

By 2024, as generative AI hit its inflection point, it was clear the legal industry was on the verge of real disruption. With a deep understanding of both the business and practice of law, plus a strong network across law and private equity, I saw a chance to bring a practitioner’s perspective to the new wave of legal AI startups – and to help transform the industry from the inside. After conversations with mentors, I decided to pivot from M&A into legal tech. My thinking was simple: I could always return to deals later, but if I waited, the best opportunities would be gone and a handful of companies would control the entire space.

In October 2024, I joined Hebbia as the second hire in its legal vertical. There, I wore every commercial hat – sales, pipeline development, engagement, partnerships, customer success, marketing and product strategy – helping to scale the business from the ground up. While we had strong wins and I learned a tremendous amount, I realized my passion and expertise could only be fully leveraged at a company where legal wasn’t just one of many verticals, but the core focus of the business.

Why August?

After successfully interviewing with dozens of companies across the legal AI landscape, I gained a clear bird’s-eye view of the market. Unfortunately, the same frustration I had as a first-year associate still held true: too many vendors are selling software without really understanding how lawyers work. Overpromising and underdelivering had become the industry standard.

August was different from my very first conversation with Rutvik Rau, the CEO. Instead of pitching me to join the company, we broke down an M&A workflow and dug into the real pain points of a transaction. That focus on the actual practice of law was refreshing. Then I tried the product myself – within minutes, without any training, I could spin up tabular reviews, analyze suites of governance documents in Assistant, and more. It felt natural, intuitive and designed with the lawyers in mind.

Meeting more of the team only reinforced my impression: this was a group obsessed with understanding legal workflows, the pressures lawyers face and the business of law itself. Technically strong, deeply motivated and focused on building solutions that meet lawyers where they are today – August had the DNA to become the AI layer for the legal profession – which was the entire reason I pivoted from Big Law.

I joined the company in August 2025 as Head of Go-To-Market, where I’m focused on scaling the sales organization, driving GTM strategy, including marketing and branding, and leveraging my legal background and network to keep our product relentlessly lawyer-centric. The goal is simple: enable lawyers to build end-to-end AI workflows that tackle their most complex matters with speed, accuracy and impact.

We’re already working with AM Law 100 firms on privilege logs spanning thousands of documents, helping firms conduct due diligence at scale, replacing legacy legal tech tools, and assisting firms in weaponize their DMS for drafting with Quill – the first legal-specific AI drafting assistant. And we’re just getting started—we have several pilots starting this week and we’re rolling out new products in the coming weeks that will genuinely automate critical parts of legal workflows – capabilities competitors like to advertise, but which haven’t gained real traction with practicing lawyers.

Unlike many players in the legal AI market, August isn’t promising flashy, never-before-seen capabilities. Instead, we focus on partnering with lawyers to optimize the workflows they already rely on – making them faster, more efficient and more strategic. Our product is shaped by a deep understanding of how lawyers actually work, and we pair that with white glove, hands-on engagement – helping lawyers marry their subject matter expertise with the platform so they can unlock advanced use cases, and ultimately, reach the next level of lawyering.

I’m thrilled to be joining August at such an exciting time – fresh off our seed funding, moving into a new office and entering a phase of rapid growth. I’m looking forward to working with Rutvik and the team to help lawyers move beyond everyday pain points and unlock the next level of lawyering using August—driving more value for their clients while accelerating their own careers.

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[ This is a special Legal Tech Lives piece for AL by Darpit, who is GTM head at August. Thanks for the insights. You can find more about August here.]

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Legal Innovators Conferences in London and New York – November ’25

If you’d like to stay ahead of the legal AI curve then come along to Legal Innovators New York, Nov 19 + 20 and also, Legal Innovators UK – Nov 4 + 5 + 6, where the brightest minds will be sharing their insights on where we are now and where we are heading. 

Legal Innovators UK arrives first, with: Law Firm Day on Nov 4th, then Inhouse Day, on the 5th, and then our new Litigation Day on the 6th. 

Both events, as always, are organised by the Cosmonauts team! 

Please get in contact with them if you’d like to take part.