Deal Velocity, Not Billable Hours: How Crosby Uses AI to Redefine Legal Contracting

Training Data

Ryan Daniels and John Sarihan are reimagining legal services by building Crosby, an AI-powered law firm that focuses on contract negotiations to start. Rather than building legal software, they've structured their company as an actual law firm with lawyers and AI engineers working side-by-side to automate human negotiations. They've eliminated billable hours in favor of per-document pricing, achieving contract turnaround times under an hour. Ryan and John explain why the law firm structure enables faster innovation cycles, how they're using AI to predict negotiation outcomes, and their vision for agents that can simulate entire contract negotiations between parties.

Hosted by Josephine Chen, Sequoia Capital

Mentioned in this episode:

• Data processing agreement (DPA): GDPR-mandated contract between controllers and processors. Crosby handles DPAs as part of B2B contracting.

• Credence good: Economic term for services whose quality is hard to judge even after consumption. Used to explain why legal buyers value lawyers-in-the-loop and malpractice coverage.