

AI-Powered Seller
Jake Dunlap
Forget the theory. This is where real-world applications of AI in sales take center stage. Join AI and sales expert Jake, as he delivers cutting-edge insights into the future of sales - powered by AI. Whether you're in leadership, on the frontlines, or driving sales enablement, Jake will give you the practical tips you need to supercharge your sales efforts and outpace the competition. By subscribing to the podcast and newsletter, you'll get exclusive early access to all our content - before it’s available to anyone else.---Subscribe to the AI-Powered Seller Newsletter for all podcast alerts and resources. https://bit.ly/ai-powered-seller-newsletter
Episodes
Mentioned books

Jun 11, 2025 • 20min
Your Competitive Battle Cards Are Wrong. How AI Creates Dynamic Positioning That Wins 3X More Deals
Traditional battle cards are costing you deals. While your enablement team spends months creating static competitive guides, your competitors release three new features, leaving your sales team armed with outdated information that buyers can fact-check in seconds.In this episode of AI-Powered Seller, Jake Dunlap exposes why competitive battle cards are dead and demonstrates his revolutionary AI-powered approach to real-time competitive intelligence that's helping sales teams win 3x more deals against superior products.Most B2B sales reps rely on generic battle cards when they should be leveraging AI for dynamic competitive positioning. Jake reveals his exact ChatGPT prompt that analyzes competitors in real-time, identifies deal-specific landmines, and provides tactical positioning strategies that traditional sales enablement can't match.Using a live demonstration with his custom Competitive Intelligence GPT, watch Jake analyze a real competitive scenario between SalesLoft and Gong at Okta, uncovering job postings, integration details, and strategic insights that would never appear in static battle cards.This competitive intelligence episode covers:Why 91% of sales enablement battle cards fail in today's fast-moving market The critical difference between knowing features and understanding competitive positioning psychology How to identify real-time competitive threats using AI sales tools Jake's complete framework for dynamic competitive analysis and deal strategySpecific positioning tactics for different competitive scenarios and buyer stages • Warning signs your competition is outmaneuvering you with better informationEvery enterprise sales rep, sales manager, and sales enablement professional needs to be running this AI competitive analysis on every deal. The gap between traditional sellers and AI-powered sellers is widening fast - which side will you be on?📍 Chapters 00:00 Why Battle Cards Are Killing Your Deals 02:27 The Fatal Flaws of Static Competitive Intelligence 05:26 AI-Powered Dynamic Positioning Revolution08:39 Live Competitive Analysis Demo with ChatGPT 14:24 Real-Time Insights That Beat Traditional Battle Cards 17:34 The Future of Competitive Sales IntelligenceNew episodes drop every other Wednesday @ 8 AM CT / 9 AM ET►Listen and subscribe on all streaming platforms: https://open.spotify.com/show/2YSdOae5YyHNfy6UQd7iIM ►Get Jake's AI Competitive Intelligence GPT: https://community.innovativesellerbook.com/c/welcome-start-here? ►Join the AI-Powered Seller Newsletter: https://bit.ly/ai-powered-seller-newsletter ►Connect with Jake: https://www.linkedin.com/in/jakedunlap/#AISales #CompetitiveIntelligence #SalesEnablement #B2BSales #ChatGPTforSales #SalesAI #BattleCards #CompetitiveSales #SalesStrategy #B2BSellingTips #SalesProcess #DynamicPositioning #RealTimeIntelligence

May 28, 2025 • 26min
‘Hidden’ Decision Makers? How AI Maps Internal Politics Before They Kill Your Deal
Your champion just went silent. That $100K deal you've been forecasting is officially dead, killed by someone in a completely different department you never knew existed.In this episode of AI-Powered Seller, Jake Dunlap reveals how to use AI for sales stakeholder mapping to identify the TRUE power dynamics in any organization before your deal gets derailed by internal politics.Most B2B sellers focus on organizational hierarchy when they should be mapping the "powerarchy", the real influence networks that determine whether enterprise deals live or die. Jake demonstrates his exact AI sales prompt that identifies ghost stakeholders, maps informal approval processes, and gives you tactical strategies to navigate complex organizational politics in B2B sales.This sales AI episode covers:Why traditional B2B stakeholder mapping fails in today's complex buying environmentThe difference between your sales champion and THE decision maker (and why it matters for deal closing)How to identify the "shadow CIO" and other hidden decision makers using AIJake's complete AI framework for political deal analysis and sales strategySpecific discovery questions to ask different stakeholders based on their motivationsWarning signs your enterprise deal is about to be torpedoed by internal dynamicsUsing a live demonstration with ChatGPT for sales, Jake walks through analyzing a fictional deal scenario, watch how AI identifies informal power structures, predicts potential deal blockers, and provides actionable next steps to win the political game in enterprise sales.Every enterprise sales rep and mid-market seller needs to be running this AI sales process on every deal.📍 Chapters00:00 Your Sales Champion Went Silent - Here's Why02:30 Why Traditional B2B Stakeholder Mapping Fails05:15 Hierarchy vs Powerarchy: Understanding Real Sales Influence08:45 Live AI Political Analysis for Sales Deals15:20 Tactical Next Steps and Enterprise Deal Warning Signs18:30 How to Future-Proof Against Political Sales LandminesNew episodes drop every other Wednesday @ 8 AM CT / 9 AM ET►Listen and subscribe on all streaming platforms: https://open.spotify.com/show/2YSdOae5YyHNfy6UQd7iIM►Join the AI-Powered Seller Newsletter: https://bit.ly/ai-powered-seller-newsletter►Connect with Jake: https://www.linkedin.com/in/jakedunlap/

May 14, 2025 • 38min
The Truth About AI From a Private Equity Veteran Managing Billions
AI won't replace salespeople. It will replace salespeople who rely on templates | AI-Powered Seller EP12In this eye-opening episode of AI-Powered Seller, Jake Dunlap sits down with Sean Mooney, Founder and CEO of Blue Wave, to explore the uncomfortable truth about AI's impact on sales teams.While most leaders are panicking about AI replacing their teams, they're missing the real threat: AI will first replace the salespeople who've been trained only to follow scripts and processes without adding unique value.Sean, who advises hundreds of PE firms and their portfolio companies on AI implementation, shares his insider perspective on:Why template-focused sellers are most vulnerable to AI disruptionHow the remote work era eliminated the learning-by-osmosis that created great sellersThe three critical implementation roadblocks 80% of companies hit with AIWhy creativity is becoming the most valuable skill in modern sellingHow custom GPTs are eliminating the need for complex promptingIf you're a sales professional worried about your future or a leader wondering how to implement AI effectively, this conversation provides the strategic framework you need right now.The skills that make sellers irreplaceable in the AI era aren't what most think. Discover what they are in this must-watch episode.📍 Chapters 00:00 Introduction to Sean Mooney02:15 The Template Generation Problem in Sales05:40 Who AI Will Replace First (And Why)10:23 Three Implementation Roadblocks to Avoid15:37 Making AI a Tactic vs a Technology22:14 Why Creativity Trumps Process28:45 Custom GPTs and the End of Prompting 34:19 Future-Proofing Your Sales CareerNew episodes drop every other Wednesday @ 8 AM CT / 9 AM ET►Listen and subscribe on all streaming platforms: https://open.spotify.com/show/2YSdOae5YyHNfy6UQd7iIM►Join the AI-Powered Seller Newsletter: https://bit.ly/ai-powered-seller-newsletter►Connect with Jake: https://www.linkedin.com/in/jakedunlap/

Apr 30, 2025 • 25min
How To Make Your Forecast Bulletproof
Bulletproof your sales deals in just 5 minutes with this custom AI tool that reveals what your prospects REALLY want. In this episode, I'll show you how AI can uncover hidden motivations that traditional discovery completely misses.Most sellers lose deals because they never truly understand what their buyers care about, even when prospects tell them directly! This revolutionary post-call analysis framework will transform your close rates and is my most tactical, game-changing episode yet.Discover how to decode subtle buyer signals, identify true priorities, and catch objection precursors before they derail your deals. I'll reveal the exact custom GPT prompt that my team and I use on our own deals, and we're giving it to you for FREE. This is the intelligence gap that separates reps hitting 120% quota from those struggling at 85%.Key Takeaways🔴 Sales Trends. Buyers are hiding their true motivations. Learn why traditional discovery is failing and how AI can uncover what prospects aren't telling you directly.🔴 Tech Trends. Post-call AI analysis is revolutionizing deal intelligence. Get the exact custom GPT prompt we use to bulletproof our own deals.🔴 Bonus: In Practice. See a real-world example of how this AI tool analyzed my actual sales call and revealed priorities I missed.🔴 Tactical Action Plan. Implement this 5-minute post-call routine to transform your close rates immediately.📍 Chapters00:00 Introduction01:38 Why Traditional Discovery is Failing05:41 The AI-Powered Deal Analysis Framework09:34 Real-World Example & Results11:00 How to Implement This Today#AIPoweredSeller #SalesIntelligence #AIforSales #customGPT #modernsales #discoveryprocess #salespsychology #dealintelligence #salesautomation #innovativeseller #createthefuture #2025salesstrategy #salesleadership #salessuccess #b2bsales #aiforsales #b2bsalestipsJake Dunlap, CEO and Founder of Skaled Consulting is an industry influencer and C-Level Sales leader with more than a decade of experience. Jake has developed and led high-performing sales and operational functions for Fortune 500, Global 2000, and start-up organizations. Jake and the team at Skaled specialize in building out repeatable, sustainable processes. As a thought leader with more than 22,000 followers across his platforms, Jake's audience gains valuable insights into scaling an organization, sales best practices, and general career motivation. Prior to Skaled, Jake was the first sales hire and VP of Sales at Glassdoor which was acquired by Recruit Holdings for $1.2Billion in 2018.► Connect with Jake DunlapLinkedIn: /jakedunlapInstagram: /jake_dunlap_Twitter: https://x.com/jaketdunlapWebsite: https://www.jakedunlap.com/

Apr 17, 2025 • 28min
How To Get 5X More Sales Meetings Using AI | ChatGPT For Outbound Prospecting Strategy
Traditional outbound sales methods are ineffective in today’s fast-paced market. The speaker shares a revolutionary AI-driven strategy that can increase sales meetings by five times. Learn how to leverage ChatGPT to create personalized white papers and custom podcast episodes in record time. Discover how to avoid pitfalls of automated approaches and instead embrace scalable solutions for effective outreach. This podcast provides practical techniques that can transform your sales team’s performance immediately!

Apr 2, 2025 • 22min
Why Your IT Team Is Sabotaging Your AI Strategy
IT is RUINING many companies’ Generative AI strategy. AI is not just an IT decision. It’s a business decision. But for too many companies, outdated fears and IT roadblocks are sabotaging AI adoption and killing productivity.In this episode, Jake Dunlap takes on the five biggest barriers IT is putting up against generative AI and lays out exactly how to break through them. Whether you’re a sales rep trying to use AI or a leader pushing for adoption, this is the playbook for moving forward.Data security & privacy – Why fears from 2023 are holding companies back and what’s actually true todayIntegration complexity – Stop overthinking AI strategy and start integrating at the role levelLack of control – AI outputs are improving fast. Are humans really giving better advice?ROI concerns – The real numbers behind AI adoption and how to quantify its impactOngoing Support & Maintenance – Why AI is easier to manage than most sales tech you’re already usingIf your company is dragging its feet on AI adoption, this episode arms you with the facts to push past hesitation and finally implement AI in a way that actually works.You’ll want to share this episode with your IT team and sales leadership. It’s time to get AI over the hump.Join the AI-Powered Seller Newsletter: https://bit.ly/ai-powered-seller-newsletter Sign up for Custom GPTs: https://link.meetjourney.ai/aff_ad?campaign_id=4859&aff_id=2751&source=Jake-KD-Podcast&hostNameId=24435 Connect with Jake: https://www.linkedin.com/in/jakedunlap/

Mar 19, 2025 • 16min
3 Ways to Implement GenAI to 10X Your Sales Productivity
Unlock the secrets to skyrocketing sales productivity with AI! Discover how advanced prompting techniques can amplify efficiency and streamline tasks. Learn about role-based AI agents that minimize manual work, giving your team more time to sell. Explore process automation and how it enhances workflow without sidelining human creativity. Plus, delve into real-world applications like rapid content creation and discovery call preparation. Find out when AI-powered selling crosses the line from smart to questionable!

Mar 5, 2025 • 18min
Sam Altman’s AI Sales Bombshell: Did OpenAI just replace SDRs for good?
Discover the groundbreaking shift as AI takes charge of B2B sales, handling everything from lead research to booking meetings without human input. Sam Altman’s announcement reveals how AI systems are streamlining sales processes, posing risks to traditional roles. The podcast dives into the growing disparity between AI-adopting companies and those lagging behind, while emphasizing the need for sales teams to adapt rapidly. Automation may enhance productivity, but the balance with human interactions remains crucial for future success.

Feb 19, 2025 • 31min
The 3 Skills Every Seller Needs to Survive the AI Shift
In this enlightening conversation, ChatGPT, OpenAI's advanced reasoning model, shares key insights into the future of B2B sales. The discussion highlights the potential timeline for AI replacing mid-level sellers and emphasizes the three essential skills needed to thrive in this new landscape. ChatGPT stresses the importance of ongoing learning and relationship-building, while revealing how generative AI can dramatically boost productivity and enhance sales quality. A roadmap for sellers to adapt and stay relevant is laid out with practical advice for immediate implementation.

Feb 5, 2025 • 33min
Should Sales Teams be Worried? What Generative AI Means for Marketing and Product Teams
Generative AI is shaking up marketing and product development, driving creativity and enhancing strategies. It plays a key role in crafting compelling website copy and product descriptions while underlining the importance of human oversight. The podcast discusses data-driven decision-making and emotional engagement in content creation. It emphasizes collaboration between sales and marketing teams, showcasing AI as a transformative tool rather than a threat, inviting listeners to embrace innovation in their businesses.