The Canadian software company won by making the unglamorous machinery of a law firm work online. Its US$1 billion vLex deal is a much riskier bet: that the same company can help run the office and reason over the law.
Billables AI is a San Francisco startup that runs quietly in the background of a lawyer's workday, watching the email, documents, calls, and calendar entries flow past, and turning them into finished, billable time entries - descriptions and all. Founded in 2023 by a team from SambaNova, Pinterest, and Mya Systems, the company argues that law firms lose real money not because lawyers do not work, but because they forget to write down that they did. It has raised roughly $14 million across a 2024 seed and a 2026 Series A, and now sells its passive, API-based timekeeping to hundreds of midmarket law firms.