Why do so many well-funded products still struggle with adoption? Mark Brehaut, Head of Design at Clair, joins us to unpack how design directly impacts activation, retention, and business performance — especially in high-stakes industries like FinTech.

From onboarding friction and time-to-value to validating assumptions before they hit production, Mark explains how human-centered design moves beyond aesthetics and becomes a measurable growth lever. We also dig into AI-assisted tooling, compliance constraints, and why great design is often invisible but still measurable.

If AI is already embedded in your teams’ workflows, are you leading it — or reacting to it? This week, Holly Laiveling, CTO at FEG Investment Advisors, shares what enterprise AI adoption really looks like inside complex, regulated environments. As generative AI moves from experiment to everyday tool, we break down how technology leaders can shift from gatekeeper to enabler through practical AI governance, tiered access models, and production-ready guardrails.
James and Holly also explore how to buy back time through automation, close the judgment gap, and evolve IT from control center to strategic partner.

If AI is the future of infrastructure, why does production still feel experimental? Joel Vasallo, Senior Director of Platform Engineering at TAG (The Aspen Group), joins us to explore what AI adoption actually looks like inside real production environments. From agent gateways and MCP servers to AI-assisted monitoring, we discuss the operational tradeoffs, why many pilots never scale, and what it really takes to move from cloud-native to AI-native.