How to CEO: The Path to $10M (Pete Caputa, Databox Edition)

What does it really take to grow from $50K to $10M ARR? In this episode of How to CEO, I talk with Peter Caputa, CEO of Databox, who took the company from early revenue struggles to $10M ARR. We dive into the hard choices CEOs face at each growth stage—from being an individual contributor to building a leadership team. Peter shares why he hired a VP of Marketing before Sales, how his job changes every six months, and how Databox uses a focused OKR system to stay on track. If you're scaling your company past the $1M, $5M, or $10M milestones, this is a must-watch.