In this episode of The AI-Powered Seller, Jake Dunlap sits down with Ryan Staley (Founder & CEO of Whale Boss) to break down the 2026 AI mindset shift every CRO, VP Sales, and frontline rep needs right now.
If you’re being asked to do more with less, increase personalization, and keep pipeline moving in a noisy market, this is your tactical playbook. Ryan and Jake go beyond basic “prompting tips” and show how to train AI like a digital teammate — not a tool you poke for answers — so it can take on multi-step work across research, deal strategy, enablement, and leadership workflows.
In this conversation, you’ll learn:
✅ The difference between a prompted assistant vs. a true digital teammate
✅ The top AI teammates to build first (account research, next-best-action, deal strategy)
✅ Why AI “liberates intelligence” and how to avoid the AI pit of despair
✅ What’s really holding sales orgs back from adoption (overwhelm + no top-down sponsorship)
✅ How to talk ROI in a way CFOs actually buy
✅ What’s coming next: agent orchestration, Cursor 2–style multi-agent management, and everyone becoming an “AI manager”
Whether you’re a rep trying to level up fast or a leader redesigning roles for the AI era, this episode will help you move from AI curiosity to AI execution.
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⭐ If you got value, drop a comment: what digital teammate would save you the most time this week?
📩 Share this with one sales leader or rep who needs a 2-year edge.
Connect with us:
Jake Dunlap on LinkedIn: https://www.linkedin.com/in/jakedunlap/
Ryan Staley on LinkedIn: https://www.linkedin.com/in/ryan-staley/
Skaled: https://skaled.com/
Whale Boss: https://ryanstaley.io/
#AIPoweredSeller #SalesAI #GenerativeAI #SalesLeadership #DigitalTeammates
