Chronologies have become one of legal tech’s hottest categories, with a wave of AI startups promising to turn a messy evidentiary record into a structured timeline in minutes. Jeff Kerr and his company Casefleet were more than a decade ahead of the pack.
Kerr finished law school in 2010 and made what he calls the crazy decision to start a law firm as his first job after graduating. Running an employment practice, he found that winning cases came down to knowing the chronology cold. But the only tools for building one were a Word document and a lot of patience. So he taught himself to code, left practice in 2015, and founded Casefleet.
On this episode of LawNext, Kerr joins me to discuss what a decade of building fact-management software looks like now that AI has arrived. Last month, Casefleet launched Casey, a conversational AI agent that proposes facts, links them to legal issues, and drafts documents — with a citation engine that rejects any citation not matching the exact text of the underlying document.
Kerr deliberately draws a hard line on what he will let his AI do. Casefleet’s agent is fully agentic in the sense of researching and iterating on its own, he says, but it stays read-only – it will not send emails, make calls, or file anything.
Among the other topics we cover:
Why Casefleet’s pre-AI data model turned out to be the right foundation for AI, and why classic Casefleet still runs alongside Casey. #
The company’s move back toward e-discovery, including newly added document production, and why Kerr isn’t chasing terabyte-scale cases. #
What happens to specialized litigation tools if the frontier AI labs push further into legal. #
Why Casefleet, profitable since 2018 and largely bootstrapped, may raise outside capital in the coming year.
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