When a company moves about 1% of the country's GDP in a year, you would expect its revenue chief to lean on experience. Jonathan Leaf says the opposite: the old principles, old ways of working and old decision frameworks all need rethinking, starting with his own.

Episode 92 features Jonathan Leaf, Chief Revenue Officer at BILL, the financial operations platform trusted by close to half a million businesses and more than 9,500 accounting firms. Jonathan owns BILL's entire global go-to-market organization: sales, marketing, customer success, support, revenue operations, enablement and partnerships. Before BILL he was Chief Revenue Officer at BambooHR, SVP of Commercial Sales at RingCentral, where he led a 600-plus person team supporting over $2 billion in annual recurring revenue, and a sales leader at AWS during the public cloud boom.

What you will take away:

1. Why using AI to make old processes a little faster is "optimizing our past," and how to make bolder bets that redefine the work instead.
2. The unglamorous wins that matter most: an AI agent for W-9 creation that 175,000 BILL customers adopted almost immediately, and fraud prevention that has saved customers tens, if not hundreds, of millions of dollars.
3. Why, in a world where everyone is trying to AI everything, showing up, shaking hands and building trust is still the thing that cannot be replaced.

Jonathan also shares why he believes the fastest learner in the seat now beats the best domain expert, what the cloud migration era taught him about which companies pull ahead, why pricing for firms is shifting toward outcomes over hours, and why his team probably does not want to work for an agent.

Thank you to BILL for supporting the Accounting Leads Now podcast.

eliminate, automate, delegate.

Connect with Jonathan:
LinkedIn: https://www.linkedin.com/in/jonathan-leaf
BILL: https://www.bill.com

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