When the internet arrived, it didn't just add a channel – it redrew roles, teams, and entire org charts. AI is doing the same, faster. The "product engineer" – one person who ships product, not just code – is showing up everywhere, and some teams are now audiences of one. For CTOs and CIOs the question isn't whether this is real; it is what to do about your org. In this workshop we look back at how the internet reshaped technology organizations, then work forward: what roles emerge, which ones compress, and how the org chart should respond. Participants apply my ownership-organizational model to their own company and leave with a concrete set of role and structural changes to test.

We cover the new roles showing up in AI-era engineering organizations (product engineer, agent operator, platform owner, and others), walk through the ownership-organizational model as a tool for deciding who owns what when teams shrink and tools amplify, redesign one team or function from a participant's own org, and end with peer pressure-testing. Everyone should leave with a clear answer to the question: do I still need PMs, TPMs, and engineering managers the way I did in 2023?

For CTOs, CIOs, VPs of Engineering, and heads of product who are actively reshaping their organizations and hiring plans in response to AI.

Every CTO and CIO in digital signage is being asked the same question right now: what is our AI strategy? Everyone is running around, everyone is confused, everyone needs to transform their company - but nobody agrees on how. In this session I argue that most transformation plans fail because they treat AI like the next piece of software to roll out. It isn't. AI changes the economics of software development itself, which means it reshapes vision, strategy, organization, and roles, not just the product roadmap. When building features becomes radically cheap, what happens to companies whose moat was "we can build it"? This session is a guide for technology leaders on what actually changes, what doesn't, and how to land on the winning side of this shift.

Attendees leave with a working model for separating AI-as-software-feature from AI-as-economic-shift, three failure patterns I see repeatedly in CTO-led AI transformations, a framework for deciding what to centralize and what to push to teams, and a set of concrete questions to put on their next leadership-team agenda.

For CTOs, CIOs, VPs of Engineering, and heads of product at digital signage platforms, integrators, and retail-tech companies.