What happens when you stop thinking about “training” and start designing a revenue architecture? In this episode, we down with Sean Reay - a seasoned revenue enablement leader with experience at companies like Outreach and Canva, and now leading enablement for an AI-first CX company, Intercom. We unpack how AI, enablement, customer education, and customer success are converging into one continuous fabric of learning that spans your entire go-to-market motion. This episode dives into ideas like an “operating system for execution that reduces friction,” why many traditional LMS-centric approaches need to evolve (or die), and how AI agents can finally deliver “learning in the flow of work” instead of more information overload. We explore practical patterns - from conversational intelligence tools to AI roleplay and contextual knowledge delivery in Slack - that help revenue and CS teams ramp faster, execute with clarity, and deliver truly personalized experiences at scale. If you’re in Customer Education, Enablement, or Customer Success and trying to make sense of AI, this conversation is a rich, tactical blueprint.
Key Takeaways:
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