O C F I T B L O G Legal ROSS Cofounder Returns To Legal Tech with Startup Using AI To Surface Judges’ Decision-Making Patterns

ROSS Cofounder Returns To Legal Tech with Startup Using AI To Surface Judges’ Decision-Making Patterns

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Jimoh Ovbiagele, cofounder in 2014 of the now-shuttered AI legal research startup ROSS Intelligence, is returning to legal tech as chief executive officer of a new startup, Bench IQ, that says it is using generative AI to provide comprehensive insights into the decision-making patterns of judges — based not just on their written rulings, but also their rulings from the bench.

The Toronto-based company recently closed a $2.1 million pre-seed funding round led by two venture capital firms, Maple, which invests in companies with Canadian roots, and Haystack, which invests in early-stage companies.

Also contributing to the round were Jason Boehmig, CEO of Ironclad; Qasar Younis, CEO of Applied Intuition and former COO of Y-Combinator; law firms Cooley, Fenwick, and Wilson Sonsini; senior partners at Kirkland & Ellis; and others, including Ovbiagele’s former ROSS cofounder Andrew Arruda, who is now CEO of the health data company Flexpa.

In an interview Tuesday, Ovbiagele said the idea for the company originated from Jeffrey Gettleman, a former partner at Kirkland & Ellis who is now Bench IQ’s cofounder and vice president of legal services.

(Pictured above are cofounders Gettleman, Maxim Isakov, Bench IQ’s chief technology officer, and Ovbiagele.)

Insights Into Judges’ Decision-Making

Although Ovbiagele said he cannot yet provide specific details about the company’s technology due to pending patents, he said that the company has compiled a new dataset and that it will use large language models (LLMs) to provide comprehensive insights into the decision-making patterns of judges, covering 100% of their rulings.

“We’re trying to solve a longstanding problem in the legal field, and that is that judges only write judicial opinions for 3% of rulings,” Ovbiagele said. “So often when attorneys are writing court documents or preparing for oral arguments and they want to know what their judge thinks about different issues in their case, they have very little information to go off of. That’s the problem that we are solving with Bench IQ.”

He distinguished Bench IQ from legal analytics companies such as Lex Machina or Pre/Dicta.

“They give you statistics around judicial behavior,” he said. “They tell you what judges have done, but they don’t tell you why judges did what they did. They’re descriptive rather than explanatory. What we offer are explanatory insights into judges’ rulings.”

Lawyers tend to use traditional legal analytics products at the front end of a litigation, to help their clients determine whether it is worth investing in going forward with the case, he said.

“But just because a tool says that a judge denies motions for summary judgment 90% of the time doesn’t mean that you’re not going to file the motion for summary judgment. You want to know why that’s the case and in what circumstances have they made exceptions. This is the kind of information that our tool can provide.”

The product is already in use at 12 of the 100 largest U.S. firms, Ovbiagele said, although he is not currently free to identify which firms. “They’re actively using the product on live cases, and it’s already informing their legal strategies.

The product, which launched to those 12 firms in January, currently covers U.S. federal courts. The company’s roadmap calls for it to eventually expand into state courts as well.

While the initial users are large firms, Ovbiagele said this is a product designed for firms of all sizes, from solos on up, and that it will offer flexible pricing to fit with different sized firms.

Although still in somewhat of a beta mode, the product will be generally available in the second half of this year, he said.

A Return to Legal Tech

Ovbiagele was a 21-year-old computer scientist when he, Arruda, then a practicing lawyer, and another computer scientist, Pargles Dall’Oglio, founded ROSS a decade ago. Another member of the founding team, Maxim Isakov, is joining Ovbiagele at Bench IQ as a cofounder and chief technology officer. 

As I recounted in a 2019 post, ROSS emerged out of the University of Toronto as a student-built entrant in a cognitive-computing competition staged by IBM to develop applications for its Watson computer. ROSS’s prototype won the competition, earning them a write-up on the front page of The Globe and Mail – which touted ROSS as the future junior associate at Bay Street law firms – and serving as a springboard for the company’s rapid acceleration.

In short order, the founders were invited to Silicon Valley to participate in the prestigious Y-Combinator startup incubator. Denton’s NextLaw Labs made ROSS one of its earliest investments. In 2015, they secured $4.3 million in seed funding and then, two years later, another $8.7 million in Series A funding. In 2017, Forbes named the three founders to its “30 Under 30.” My 2019 post detailed my visit to ROSS’s Toronto research and development office. 

But ROSS’s trajectory changed in 2020, when legal research giant Thomson Reuters filed a lawsuit against ROSS, alleging that it stole content from Westlaw to build its own competing legal research product. ROSS did this, TR alleged, by “intentionally and knowingly” inducing the legal research and writing company LegalEase Solutions to use its Westlaw account to deliver Westlaw data to ROSS en masse.

The lawsuit forced ROSS to shut down its operations, which it did effective Jan. 31, 2021. But ROSS vowed at the time to continue fighting the lawsuit, which it characterized as a bullying tactic by TR to shut down a potential rival, and that lawsuit continues to move forward. 

See all my coverage of the Thomson Reuters-ROSS litigation.

After ROSS shut down, Ovbiagele left legal tech “to recharge my batteries,” he told me, working for a period as a product manager at Coinbase.

“But then, after my batteries got to about 50%, the startup itch came back with a vengeance,” he said. “So that’s what led me here.”

A ‘Legal Reconnaissance Platform’

Cofounder Gettleman, who originally conceived the idea for Bench IQ during his tenure at Kirkland & Ellis, said in a statement provided by the company, “Over almost two decades at Kirkland, I learned how vital it is to understand how a judge thinks to achieve your objective. Bench IQ allows lawyers to understand their judge in a way no other resource can. It helps them build arguments they can be confident in and deliver the desired results.”

Investor Andre Charoo, general partner at Maple, said, “We think Bench IQ has the potential to create the new standard of law — one that is based on understanding the players in the legal game, not just about the rules of the game. The team has uncovered a unique insight that is not obvious to most, and we’re incredibly excited to be part of their journey in changing the legal industry as we know it.”

Another investor, Aashay Sanghvi, partner at Haystack Ventures, said, “Bench IQ immediately stood out to us as a novel way to use LLMs to solve a persistent challenge in legal research. We are delighted to partner with Jimoh, Maxim, and Jeffrey as they build the leading legal reconnaissance platform.”

LawNext Episode 48: ROSS Intelligence Founders Andrew Arruda and Jimoh Ovbiagele

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