AI-Powered Seller

AI Bubble or Breakout: Are you building real, needle-moving workflows with AI, or collecting “bubble” use cases that create overlap and extra change management?In this episode of AI Powered Seller, Jake Dunlap explains why the “AI bubble” is not AI itself, but the noise on top of it, including duplicate tools, overlapping features, and organizations investing without clear ownership. He breaks down how GTM leaders and frontline sellers can evaluate AI the right way: start with the revenue bottleneck, then choose technology that solves it. Innovative SellerYou’ll also get Jake’s tactical seller playbook for adopting GenAI in a sustainable way:Identify your three most painful tasksRefine AI outputs so they sound like youBuild a simple ongoing roadmap so you don’t try to solve everything at onceCheck Out: JourneyAI (free trial): https://meetjourney.ai/Jake Dunlap – https://www.linkedin.com/in/jakedunlap/Skaled - https://skaled.com/If you got value from this episode, share it with a teammate in Sales, RevOps, Enablement, or Marketing, and make sure you’re subscribed so you don’t miss the next drop.

In this episode, Jake is joined by revenue leader Chris Casula for a highly tactical conversation on how AI is transforming pipeline management, forecasting accuracy, and GTM productivity.Chris shares hard-won insights from managing enterprise and transactional sales teams, and breaks down why forecasting has historically been the “bane of sales” — and why it’s not the reps’ fault.You’ll also hear real examples of how AI surfaces buying signals, identifies bottlenecks in the sales process, improves win rates, and enables managers to coach more effectively.In this episode, we cover: • Why traditional forecasting models fail • Which AI signals improve top-of-funnel accuracy • How to identify hidden deal risks with AI • Why deal reviews are the first workflow leaders should automate • A new way to think about pipeline coverage • The mindset shift every sales leader must make in 2025 • What predictable revenue will actually look like by 2026If you’re a frontline rep, manager, or revenue leader looking to drive predictable revenue and adopt AI the right way, this episode will give you one clear takeaway you can act on today.

In Part 2 of our AI in Sales series, Jake Dunlap breaks down how top sellers are moving from basic AI assistance to fully automated workflows that run before, during, and after their workday. This episode shows how modern reps are scaling their daily workflow using automation that handles research, meeting prep, intent analysis, follow-ups, and CRM updates—freeing them to focus on higher-value conversations.Jake also explores what AI-enabled leadership looks like today, and how managers can use automation to surface coaching opportunities, review call quality, and improve overall team performance without hours of manual analysis.What you’ll learn: • How AI can complete account research, intent scoring, and meeting prep automatically • How follow-ups, summaries, and CRM activity can be fully automated • How top sellers optimize outbound using real-time performance insights • Practical examples of digital teammates that improve deal execution • How modern leaders use AI to scale coaching and increase visibilityLinks from the episode: 👉 JourneyAI: https://meetjourney.ai/👉 Performance Pulse: https://www.revoptics.co/services/sales-reporting👉 Superhuman: https://superhuman.com👉 AI Sales Training & Certifications for GTM Teams: https://skaled.com/services/ai-sales-training/Connect with Us: https://www.linkedin.com/in/jakedunlap/https://www.linkedin.com/company/skaled/ https://skaled.com/

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.👉 Subscribe for weekly episodes with real GenAI sales use cases.⭐ 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

🔥 Why Most AI Deployments Fail (And How Real Sellers Win With It) 🤖Is AI actually helping sales teams — or just creating more noise? Why are so many companies struggling to get ROI from their AI investments? The brutal truth: it's often caused by broken processes, bad expectations, and outdated leadership. 😬In this episode, Jake is joined by Ryan Cahill, a veteran GTM architect and operator who has helped scale revenue teams across SaaS. Ryan breaks down exactly why AI fails in most organizations — and what high-performing teams do differently to turn AI into a true competitive advantage.He reveals the tactical playbook that top teams use to improve outbound, accelerate deal cycles, and make reps instantly smarter using AI.🔥 What you'll learn in this episode (Don't miss the real truth behind AI!):✨ The Core Problem: Why companies expect AI to be a magic wand — and why that mindset guarantees failure.🧠 The Setup Mistake: The missing pre-work every team skips that destroys ROI before AI ever launches.⚙️ Human-in-the-Loop: How elite teams combine rep judgment + AI to outperform both humans and automation alone.📈 Outbound Breakthroughs: Why AI now outperforms template-based SDR outreach — and how reps can stay relevant.🔍 Instant Expertise: How reps can now learn any industry in 10 minutes and run world-class discovery.🏆 The GTM Advantage: How AI lets leaders analyze their business, pivot faster, and double down on what actually works.This isn’t about more tools — it’s about better strategy, better execution, and smarter humans using AI the right way.👉 Tune in and learn how to become a modern, AI-powered, outcome-driven seller!