In this episode, Jack is joined by Ryan Roccon, CFO and COO of Zapier. They discuss how Zapier’s automation platform is adapting to an AI environment in which companies can build applications and agents quickly but still need reliability, visibility, permissions, auditability, and cost control when those workflows move into production. Roccon explains how Zapier is combining deterministic automation with agentic functionality and how that shift is influencing product development, pricing, organizational design, and revenue priorities.
The conversation also examines Roccon’s capital-allocation philosophy: maintaining cash flow discipline while challenging the organization to identify opportunities compelling enough to justify breaking its own rules. Inside finance, he describes AI-enabled automation across close, reconciliations, scenario analysis, tax, and other workflows.
Roccon also shares the thinking behind Zapier’s “Path to a Billion,” a long-range plan designed to explain why the company needed to move beyond a purely self-service model and develop enterprise sales capabilities. He reflects on the resistance that shift created and why CFOs must spend as much time making the financial story understandable as they do building the model itself. Later, he discusses executive judgment, reversible versus irreversible decisions, peer networking, and why his current priorities extend beyond finance to product, go-to-market clarity, and customer adoption.