Episodes

  • ‘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/

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    26 mins
  • The Truth About AI From a Private Equity Veteran Managing Billions
    May 14 2025

    AI won't replace salespeople. It will replace salespeople who rely on templates | AI-Powered Seller EP12

    In 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 disruption
    • How the remote work era eliminated the learning-by-osmosis that created great sellers
    • The three critical implementation roadblocks 80% of companies hit with AI
    • Why creativity is becoming the most valuable skill in modern selling
    • How custom GPTs are eliminating the need for complex prompting

    If 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 Mooney

    02:15 The Template Generation Problem in Sales

    05:40 Who AI Will Replace First (And Why)

    10:23 Three Implementation Roadblocks to Avoid

    15:37 Making AI a Tactic vs a Technology

    22:14 Why Creativity Trumps Process

    28:45 Custom GPTs and the End of Prompting 34:19 Future-Proofing Your Sales Career

    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/

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    38 mins
  • How To Make Your Forecast Bulletproof
    Apr 30 2025

    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.

    📍 Chapters

    00:00 Introduction

    01:38 Why Traditional Discovery is Failing

    05:41 The AI-Powered Deal Analysis Framework

    09:34 Real-World Example & Results

    11:00 How to Implement This Today

    #AIPoweredSeller #SalesIntelligence #AIforSales #customGPT #modernsales #discoveryprocess #salespsychology #dealintelligence #salesautomation #innovativeseller #createthefuture #2025salesstrategy #salesleadership #salessuccess #b2bsales #aiforsales #b2bsalestips

    Jake 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 Dunlap

    LinkedIn: /jakedunlap

    Instagram: /jake_dunlap_

    Twitter: https://x.com/jaketdunlap

    Website: https://www.jakedunlap.com/

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    25 mins
  • How To Get 5X More Sales Meetings Using AI | ChatGPT For Outbound Prospecting Strategy
    Apr 17 2025

    Traditional outbound is dead. In this episode of AI-Powered Seller, Jake Dunlap reveals how he's getting 5X more meetings with an AI-powered outbound strategy that completely rewrites the sales playbook.

    Only 20% of sales teams hit their outbound numbers last year. They're using outdated tactics from when personalization was standard, not the exception.

    Jake breaks down his two-part AI outbound strategy:

    - How to create personalized white papers for prospects in 20 minutes using ChatGPT
    - How to generate custom podcast episodes about your prospect's business in 10 minutes
    - Why "automated" killed effectiveness (and how "scalable" brings it back)
    - The exact AI tools generating hyper-personalized content with minimal effort

    Modern buyers need experts who understand their world. Generic outreach doesn't cut it anymore. Jake demonstrates these techniques live and shows exactly how to implement them on your team today.

    Don't let your competitors discover this strategy first. Watch now to transform your outbound approach and start booking more meetings immediately.

    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/

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    28 mins
  • Why Your IT Team Is Sabotaging Your AI Strategy
    Apr 2 2025

    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 today
    Integration complexity – Stop overthinking AI strategy and start integrating at the role level
    Lack 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 impact
    Ongoing Support & Maintenance – Why AI is easier to manage than most sales tech you’re already using

    If 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/

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    22 mins
  • 3 Ways to Implement GenAI to 10X Your Sales Productivity
    Mar 19 2025

    Sales teams know AI can automate tasks, streamline workflows, and generate insights but most aren’t even scratching the surface of its full potential.

    Reps and leaders keep hearing “use AI to sell smarter!” but what does that actually look like in practice? This episode is the tactical breakdown you’ve been waiting for.

    Advanced prompting – How using high-quality AI models with better prompts can 10x productivity
    Role-based AI agents – The game-changing way to eliminate manual tasks and optimize your workflow
    Process automation – Why scaling efficiency isn’t about replacing humans, but working smarter

    Jake Dunlap dives into real-world AI applications, from writing a five-page white paper in minutes to automating discovery call prep, and tackles the big question: At what point does AI-powered selling stop being smart and start feeling like cheating?

    If AI is going to be your competitive advantage, it needs to be integrated into how you work today, not some future plan.

    This episode is your step-by-step guide to making AI work for you right now.

    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/

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    16 mins
  • Sam Altman’s AI Sales Bombshell: Did OpenAI just replace SDRs for good?
    Mar 5 2025

    AI isn’t just assisting sellers anymore. It’s stepping into the process in ways that were only theorized about before.

    What happens when AI isn’t just assisting sellers but running full inbound sales motions on its own?

    That’s the reality OpenAI just put in front of us: an AI-powered B2B sales agent that can take on researching leads, qualifying them, and booking meetings without any human involvement.

    This episode will deep dive into Sam Altman’s announcement of OpenAI’s B2B sales agents with Jake’s unfiltered reaction to all that these new tools are bringing to the table. Discover what AI agents mean for the future of sales teams, the roles most at risk, and how AI is reshaping inbound sales.

    OpenAI’s latest announcement and why highlighting B2B sales is a major shift
    How AI-driven sales agents work and what tasks they’re already automating
    The growing gap between companies adopting AI and those falling behind
    What sales teams should be doing now to stay ahead of AI-driven automation

    Whether you’re an SDR, AE, or leadership, this is news you can’t afford to ignore. No speculation, no hypotheticals. It’s happening right now.

    AI IMPACT Report: https://bit.ly/ai-impact-assessment-report


    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/

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    18 mins
  • The 3 Skills Every Seller Needs to Survive the AI Shift
    Feb 19 2025

    What happens when AI doesn’t just assist sellers but starts replacing them?

    In this episode of AI-Powered Seller, Jake takes a hard look at the timeline: when AI will start automating transactional deals, when mid-level sellers will struggle to stay relevant, and what skills will actually matter in an AI-driven sales world. Forget the distant future. This shift is happening faster than you think. AI is transforming sales in real-time.

    But this isn’t just another “AI will change sales” discussion. Instead of his usual co-host, KD, Jake is joined by a different kind of guest: one of OpenAI’s most advanced reasoning models. The goal? Get straight answers on where AI is taking sales and what sellers need to do right now to stay ahead.

    What you’ll hear about in this episode:

    • The timeline for AI’s potential to replace mid-level sellers (and the roles that are at risk first)
    • The three must-have skills sellers need to stay relevant in the AI era
    • A roadmap for leveling up over the next 2-4 years and what you should be learning NOW
    • How generative AI is boosting productivity (saving hours per week + improving sales quality)


    Whether you’re an SDR, AE, or sales leader, this conversation breaks down what you need to do to stay ahead before it’s too late. No scare tactics just a data-backed breakdown that sales professionals need to hear.

    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/

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    31 mins
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