ON THIS EPISODE
➤ Why IT presentations lose executives in 30 seconds—and the backward storytelling framework that changes everything
➤ How a CFO cut AWS costs 20% in three weeks through daily DevOps partnership sessions
➤ The Five Boss Model: Why your CFO wants to fund IT projects but can’t understand your proposals
➤ Innovation budget reality: Why 15-20% waste is expected and how to frame experimentation
➤ The Gemba Principle: Japanese leadership concept for IT-business cross-cultural integration
➤ KeyBanc benchmarking system to justify IT spend as percentage of revenue
What happens when a CFO reveals he has five different bosses?
Bill Dillmeier isn’t your typical rearview-mirror CFO. As a finance business partner with five simultaneous bosses—head of sales, head of marketing, head of product, head of engineering, and head of operations—he offers a rare insider perspective on what finance actually wants from IT leaders.
From spending three weeks reviewing AWS nightly charges with his DevOps team to defending strategic overspend to skeptical boards, Bill shares the frameworks and partnership approaches that transform IT-Finance from adversarial to strategic collaboration. He reveals why the average CTO tenure in Fortune 500/1000 companies is only 24 months, and more importantly, what IT leaders can do about it.
Bill discusses the backward storytelling framework that helps IT leaders own the room in board presentations, the Gemba principle for cross-functional integration, and why CFOs not only expect but encourage 15-20% IT budget waste on innovation and experimentation.
