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AI-Powered Seller

AI-Powered Seller

By: Jake Dunlap
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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.

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© 2025 AI-Powered Seller
Economics
Episodes
  • How OpenAI's Sales Reps Actually Use AI to Close Deals
    Aug 20 2025

    Connor from OpenAI shares how revenue teams are leveraging generative AI to transform their sales processes and achieve meaningful business outcomes beyond the initial experimentation phase. He outlines a clear pattern among successful organizations: democratizing technology access, investing in AI education, and measuring impact through improved business metrics rather than just time savings.

    • Three myths slow AI adoption: needing a massive project, assuming availability equals adoption, and waiting for AI to mature
    • Deep research capabilities fundamentally change how sales teams prepare, turning hours of work into minutes
    • Sales leaders create personalized "user guides" for team members to help AI tailor coaching approaches
    • Projects and custom GPTs serve as "homes" for deal information, enabling better handoffs and customer experiences
    • Successful executives sponsor AI initiatives, demonstrate personal usage, and recognize AI champions
    • Most powerful implementations progress from individual impact to team impact to organizational transformation
    • Future of AI includes "agentic orchestration" where AI becomes the always-on assistant for all work activities
    • Frontline sellers will need increased technical aptitude as AI becomes more integrated into sales processes

    Start using AI today rather than waiting for perfect understanding—dedicate time to learn this technology as it represents the future of sales. Try one use case at a time and share what you're learning with your team.


    Show More Show Less
    46 mins
  • Your Competitive Battle Cards Are Wrong. How AI Creates Dynamic Positioning That Wins 3X More Deals
    Jun 11 2025

    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 strategy
    • Specific positioning tactics for different competitive scenarios and buyer stages • Warning signs your competition is outmaneuvering you with better information

    Every 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 Revolution

    08:39 Live Competitive Analysis Demo with ChatGPT

    14:24 Real-Time Insights That Beat Traditional Battle Cards

    17:34 The Future of Competitive Sales Intelligence

    New 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

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    20 mins
  • ‘Hidden’ Decision Makers? How AI Maps Internal Politics Before They Kill Your Deal
    May 28 2025

    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 environment
    • The 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 AI
    • Jake's complete AI framework for political deal analysis and sales strategy
    • Specific discovery questions to ask different stakeholders based on their motivations
    • Warning signs your enterprise deal is about to be torpedoed by internal dynamics

    Using 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.

    📍 Chapters

    00:00 Your Sales Champion Went Silent - Here's Why

    02:30 Why Traditional B2B Stakeholder Mapping Fails

    05:15 Hierarchy vs Powerarchy: Understanding Real Sales Influence

    08:45 Live AI Political Analysis for Sales Deals

    15:20 Tactical Next Steps and Enterprise Deal Warning Signs

    18:30 How to Future-Proof Against Political Sales Landmines

    New 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/

    Show More Show Less
    26 mins
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