AI is reshaping software and services, and every leader is deciding where to start. On Lay of the Land, Robots & Pencils CEO Len Pagon joins host Jeffrey Stern for a 1-1 on what it takes to lead through that shift: learning by doing, working against tight deadlines, and owning the parts of the work that stay with leaders.
Lay of the Land is a Cleveland video podcast built on long conversations with the people who build and shape Cleveland and Ohio. Jeffrey opens with the obvious question for a CEO who spent 17 years as an investor and board member before coming back to lead: why jump back into the arena?
Len talks about how Robots & Pencils became an AI-first company, why learning by doing beats training, how a one-week deadline changes the way teams work, and how one person’s skill becomes a whole team’s head start.
He and Jeffrey also cover where lasting value will land as AI reshapes software and services, where leaders should start, and which parts of the work still belong to leaders, including data quality, culture, policy, and technical debt. The conversation closes with Len’s advice for this moment and his pick for a Cleveland hidden gem.
Press play to hear it all.
