Kevin Rubin on AI investment

In this episode, Jack is joined by Kevin Rubin, the CFO of Zscaler. They discuss Zscaler’s zero-trust cybersecurity model, global enterprise scale, and the strategic challenges of operating in a fast-moving threat environment. Rubin explains why disciplined experimentation is essential to AI investment and how finance helps prevent technology sprawl. The conversation also covers the evolution of the CFO role, go-to-market partnership, and forecasting sophistication. Rubin shares lessons from earlier CFO chapters—including Alteryx’s land-and-expand strategy—offering perspective on how customer insight, financial modeling, and restraint shape durable growth. Thanks to our sponsors Planful– https://www.Planful.com/ Intuit QuickBooks – https://quickbooks.intuit.com/money/ Video Timestamps & Titles 0:00 – Episode introduction and AI as experimentation 1:29 – How the CFO role keeps getting rewritten 2:57 – Kevin Rubin’s multi-chapter CFO career 4:10 – From compliance to strategic finance leadership 6:22 – Curiosity, adaptability, and understanding the business 8:32 – CFO involvement in go-to-market decisions 11:46 – Getting ahead of the curve on GTM and AI 16:18 – What Zscaler does and why zero trust matters 19:35 – First 100 days at Zscaler 22:45 – AI strategy: product, security, and operations 25:39 – Centralizing AI governance and discipline 31:09 – AI’s impact on forecasting and modeling 33:10 – Finance Strategic Moment: Alteryx land-and-expand model 36:57 – Building a scalable finance leadership team 43:54 – Priorities for the next 12 months