The AI law firm’s best feature isn’t the AI
Crosby automated contract review about as hard as anyone has. Its own lawyers say that’s not what won clients over.
A writer spent two weeks inside Crosby, a New York law firm built around AI from day one. They call themselves a “neofirm.” Half the staff came from Kirkland & Ellis, Wachtell, and Sullivan & Cromwell. The other half are engineers from Ramp and Stripe. They’ve raised $85 million.
The piece ran in late July in a publication called New Ontologies. It’s worth reading, though you should know it was written with the firm’s cooperation — the only outside sources are Crosby’s own investors and one customer.
Here’s the part that stuck with me. It has nothing to do with speed.
The number everyone will quote
Crosby runs internal contests they call “time trials.” Lawyers race to redline a contract against the clock. One finished an NDA in four minutes and fifty-three seconds using their in-house AI redlining tool.
The comparison figure in the article is roughly 58 minutes for a lawyer working without technology. That’s a 10x lift.
Be careful with that number:
It came from a teammate over Slack, not from a study.
One contract type, one known sample, one document.
The writer concedes the setting was “sterile.”
It’s directionally interesting, not a benchmark. Somebody will cite it as one within a month.
What their own lawyers found instead
Ross Weiser, one of Crosby’s lawyers, came from Sullivan & Cromwell — one of the best corporate firms in New York. He expected clients to treat an AI-native firm differently. More like software, less like a firm.
They didn’t. His words: “They want to know that they can trust us. They want to know who’s responsible. It is just so human.”
Then there’s the client side. A company called Braintrust moved all of its contracts over to Crosby. The reason they gave wasn’t the AI. It was:
Cross-checking features, so they could see the work had been checked
Detailed internal notes
Estimated-time-of-arrival metrics on important documents
Read that list again. None of it requires $85 million or an engineering team. It’s telling people where their matter stands, showing your work, and being clear about who’s accountable.
Where the judgment still lives
The best detail in the article is a small one. A lawyer accepts a screen of AI redlines with a tap, then slows down on a single clause. He deletes an “or” and types “and.”
That’s the job now: the machine handles volume, and a person decides the one thing that matters.
What I’d do with this
Pick one narrow service and publish a fixed price for it. Crosby’s real difference isn’t the AI — it’s that they sell an output instead of an hour. You can do that this week without buying anything.
Send a status update nobody asked for. One paragraph, once a week, on where things stand.
Give people an ETA and hit it. If you’re going to miss it, say so before they notice.
Make sure every client can name the person responsible for their matter. If they can’t, that’s your gap, and no tool fixes it.
Bottom line
The firm working hardest to automate legal work concluded that the human relationship got more valuable, not less. That’s either good news or a warning, depending on how you’ve been treating the relationship part.
;-)
Ernie
P.S. In the Inner Circle, we work through important AI questions together. For example, this Thursday we’re doing a session entitled: Can You Bill Clients for AI? The Ethics of Passing Costs Through. If you want to join us, sign up for the Inner Circle with a special 30 day trial for just $1.