How BILL is rebuilding for the Fortune 5 million and gearing up to take big swings on AI

For most small and midsize businesses, financial operations still look a lot like they did a decade ago. Bills get keyed in manually. Receipts pile up. W-9s get chased down at tax time. While the tools have multiplied, the work hasn't gone away. “Most finance teams work in an incredibly manual way,” says Michael Cieri, Chief Product Officer at BILL. “There's a ton of work done by finance professionals that could be automated, and could actually be done better through the use of technology.” The gap between the promise of modern financial software and the day-to-day reality of running the books at a small business is something BILL has spent nearly two decades trying to close. The company processes over 1% of US GDP in payments and has moved more than a trillion dollars across its platform – a scale that gives it both a data advantage and a particular sense of accountability. When you're handling that volume of transactions for the long tail of American businesses, the stakes of getting automation wrong are very high. Cieri joins us on the show to talk through where BILL's product thinking stands today: how Cieri's team decides when to take big swings versus make incremental improvements, how it builds and validates AI features for a high-trust domain.