Matt Millen spent years running revenue at Outreach, watching companies stall out post-onboarding, and built Regie.ai to fix the problems that sales engagement itself created. He was attaching generative AI to tools like Outreach and SalesLoft years before ChatGPT, which gives him a rare vantage point on what actually works vs. what's still hype.

In this episode, Noah and Andy get into why half of all AI POCs were failing (hint: it was both sides' fault), how Regie thinks about workflow before product, and why Matt believes "where humans enter the loop" is a brand decision, not a platform limitation. He also shares a blunt breakdown of which companies are good fits and which ones waste everyone's time, and makes the case for why the buy vs. build debate is being driven by CEOs who haven't thought through the workflow complexity underneath.

Topics Discussed:

• Why 50% of AI POCs were failing and the two-sided imbalance that caused it

• The four readiness signals Regie uses to qualify or disqualify a prospect before the POC starts

• Workflow interviews with frontline reps vs. managers and why the gap between them matters

• Shifting from day-17 sequence dumps to signal-triggered task lists with built-in call context

• Why human-in-the-loop placement is a brand decision, not a product constraint

• Seat-based pricing with bundled AI credits and how the 80/20 on data consumption actually works

• The workflow complexity case against building agentic sales in-house

• Where the SDR and AE roles are heading as agents absorb more of the top-of-funnel motion

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