In Toronto, A Legal Robot Reveals Its Innards

ROSS Intelligence is making a smart move in opening its product for anyone to try.

For AI-powered legal research startup ROSS Intelligence, it was both a blessing and a curse.

Five years ago, when it launched as a prototype developed at the University of Toronto, AI in law was still a somewhat novel concept, generating clickbait headlines about robots doing the work of lawyers.

News stories about ROSS struck a common chord, describing it as a robotic junior associate, a robotic legal researcher, and a legal research robo-lawyer.

Such headlines helped bring media attention and investor interest. In short order, ROSS’s founders had left Toronto for Silicon Valley, where they participated in the prestigious Y-Combinator startup incubator, drew an investment from Dentons’s NextLaw Labs, and secured first $4.3 million in seed funding and then another $8.7 million in Series A funding. In 2017, Forbes named ROSS’s three founders to its “30 Under 30.”

But all that attention also brought pressures and challenges. The three founders ranged in age from 21 to 25. They were inexperienced in business and in building a company. AI in legal research was a nascent field with no models for them to start from.

It was a stressful time, cofounder and CEO Andrew Arruda told me. Although they had a vision of using AI to make legal research more affordable, they had no experience in being entrepreneurs or scaling a product.

“It was a huge challenge for us to build it from scratch,” Arruda said. “We were experimenting and innovating under the spotlights, because we had a lot of media attention.”

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One consequence of that was that ROSS became secretive about showing its product. For years, the company rebuffed my requests to review it. Others told me similar stories, including law librarians and knowledge managers. Someone must have been seeing it, because the company was reporting sales, but they were strangers to me.

The reason for this secrecy, Arruda now tells me, was that they truly thought they were building something unique, and they feared that a competitor would steal it out from under them. They kept the product close to the vest, until they reached the point where they were confident that it was ready.

That point has arrived.

In June, quietly and without fanfare, ROSS changed its website to offer free trials of its product to anyone who wants one. The product that had once seemed a state secret was now open to everyone for a two-week free trial, not even a credit card required.

Then last week, at Arruda’s invitation, I spent two days at ROSS’s research and development offices in Toronto. I had unfettered access to its entire engineering and design teams. I sat in on engineering and UX team meetings. I was encouraged to ask any question I wanted of anyone I wanted.

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(Earlier today, I published an in-depth report on my visit to ROSS and what I learned about the company. You can find that at my LawSites blog: At AI Research Company ROSS, A New Stage of Transparency and Engagement.)

This new transparency is the culmination of a year of refocusing and refinement for ROSS. It has been a year of major developments for the company, including not just refinement of its product, but also a refocusing of its marketing towards smaller firms, a reconfiguration of its pricing to a monthly no-obligation subscription, and the hiring of a veteran head of engineering, Stergios Anastasiadis, formerly of Shopify and Google, to lead future development.

In the five years since it started, the glare of the media spotlight has somewhat dimmed for ROSS. The clickbait headlines have largely subsided. Meanwhile, its founders have matured, the company has matured and, it appears, its product has matured.

But the legal research market is even more competitive today than it was when ROSS started. Both long-established players and up-and-coming startups are using AI and claiming, as does ROSS, that they deliver better, more-precise results.

The proof, as they say, is in the pudding. ROSS is making a smart move in opening its product for anyone to try. By lifting the secrecy around its product, ROSS is declaring its confidence in it. Now it is for the market to judge.


Robert Ambrogi Bob AmbrogiRobert Ambrogi is a Massachusetts lawyer and journalist who has been covering legal technology and the web for more than 20 years, primarily through his blog LawSites.com. Former editor-in-chief of several legal newspapers, he is a fellow of the College of Law Practice Management and an inaugural Fastcase 50 honoree. He can be reached by email at ambrogi@gmail.com, and you can follow him on Twitter (@BobAmbrogi).

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