companies

Puzzle

AI-native accounting platform that rebuilt the general ledger to auto-categorize transactions and close the books in real time.

Puzzle Financial was founded in 2019 in San Francisco by Sasha Orloff, previously founder of the online lender LendUp, and John Cwikla. Rather than layering AI on top of an existing ledger product, the founding team rebuilt the double-entry general ledger itself, arguing that bolt-on automation runs into structural limits that a ground-up rebuild avoids. The company has raised $66.5 million across three rounds, including a $30 million round backed by General Catalyst, Felicis Ventures, and Kapor Capital. Puzzle targets venture-backed startups and the accounting firms that serve them, and connects natively to the fintech stack many startups already run on, including Stripe, Mercury, Brex, Gusto, and Bill.com. Puzzle's ledger uses different machine learning models for different tasks: classification models for transaction categorization, anomaly detection for flagging unusual entries, and a generate-then-validate process for drafting financial statements. The company describes this as 'governed automation' — nothing posts to the books without a human approving it — and offers a free tier for companies under roughly $20,000 in monthly transaction volume.

Founded

2019

Headquarters

San Francisco, United States

Sector

applications