

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

Oct 8, 2025 • 18min
Why Sales Automation Just Leveled Up: Inside OpenAI’s AgentKit
Stop asking AI for answers and start letting it act. We break down how OpenAI’s Agent Kit flips sales from reactive prompts to proactive, multi-step workflows that coordinate CRM, email, calendar, and call intelligence like an orchestra under a single baton. I walk through what launched, why it’s different from traditional automation, and how a visual Agent Builder, Chat Kit for human-in-the-loop feedback, and built-in evals make it practical for frontline reps—not just ops and engineering—to build production-ready agents in minutes.We get specific with three high-impact use cases you can clone: an inbound orchestrator that checks Salesforce, enriches with public insights, drafts a reply, and summarizes in Slack; a deal health sentry that monitors engagement, multithreading, and silence windows, then escalates with context; and a proposal producer that pulls your last call, maps to your statement-of-work template, asks clarifying questions, and outputs a Google Doc v1. Along the way, I share a story from my early career about finding conversion “quiet pockets” and how the same insight now takes thirty minutes to automate end-to-end.There are guardrails: keep the human touch for tone and senior outreach, expect occasional connector changes, and invest time upfront to define quality. But the upside is real and immediate—sellers who learn agents can 2–3x output and build compounding advantage. If you’ve ever felt buried in follow-ups, prep, and proposals, this is your way out through orchestration, not hustle theater. Subscribe, share this with your team, and tell me the first workflow you’ll automate. And if you want hands-on help, join our AI certification and leave with working agents and a repeatable playbook.

Oct 1, 2025 • 26min
AI Proficiency in Sales: Stop Dabbling, Start Deploying Digital Teammates
Most sellers say they “use AI,” but the real question is: is AI actually running your sales workflow? We pull back the curtain on what true AI proficiency looks like, why dabbling won’t keep you competitive, and how to jump from basic prompts to digital teammates that own the work. This isn’t a tool tour—it’s a working blueprint for transforming prospecting, research, coaching, and follow-through so you win more deals with less manual drag.We map the five levels of AI proficiency, from ad hoc user to multiplier, with crisp examples you can copy today. You’ll hear how a “New Account Research” teammate can scrape signals and context before you even open your CRM, how a pricing-objection specialist can produce competitor-aware responses in seconds, and how manager-trained GPTs can review call transcripts and give targeted coaching using your actual playbook. Then we zoom out and show what happens at the agent level: calendar-triggered prep, Slack clarifications, automated recaps, and draft SOWs that land in your docs without you lifting a finger. The numbers are real—a 47% productivity lift, roughly 12 hours a week back—translating into more selling time, better personalization, and cleaner pipelines.If you’re at level one, we lay out a fast track to level three: convert your best prompts into assistants, feed them product and persona context, and standardize outputs so quality is consistent. Leaders get a roadmap to become multipliers by setting a GenAI backlog, prioritizing high-impact workflows, and rolling out shared assistants across the team. Hiring is already shifting; candidates who can show live AI workflows will outrun those who “know ChatGPT.”If this guide helps, subscribe, share it with a teammate, and leave a review so more sellers find it. Want to level up faster? Explore the AI certification for sellers and frontline leaders, and test-drive the MeetJourney assistants tailored for sales teams.

Sep 24, 2025 • 46min
The Non-Linear Buyer Journey: How Top Performers Adapt and Win
Your champion just went silent. That 90% deal just died — and it wasn't killed by the person you were talking to. It was derailed by stakeholders you never knew existed.Host Jake Dunlap sits down with Gal Agha, CEO of Aligned, to break down why traditional sales methodologies like MEDPIC are failing in today's complex buying environment. With clients cutting sales cycles by 30% and increasing win rates by 15%, Gal reveals what he calls "buying process as a service."What You'll Learn:Why MEDPIC is built for 1950s buyers, not today's complex stakeholder groupsHow to use AI for scenario planning and competitive intelligenceThe difference between hierarchy and "powerarchy" in modern dealsWhy 95% of buying happens without you — and how to influence itTactical frameworks for accommodating vetted, educated, and self-service buyersKey Takeaway: The future belongs to sellers who deliver "buying process as a service" — becoming an extension of the buyer's team rather than an obstacle to navigate.Check out: The Innovative Seller: https://a.co/d/cbh8hM3JourneyAI: https://meetjourney.aiSubscribe: New episodes every week on your favorite podcast platform. Leave a review on Apple Podcasts to help us reach more sales professionals.Remember: AI won't replace sellers — sellers who know how to use AI will replace those who don't.

Sep 17, 2025 • 18min
Steal This AI Prompt And 10x Your Sales In 30 Days
Most sales reps are still doing the bare minimum before a call check LinkedIn, skim a website, then hope for the best. Winners? They’re using AI to prep in under 5 minutes, crush first impressions, and dominate quota.💡 In this episode, Jake breaks down the exact AI-powered playbook top sellers are using right now: 🔥 Step 1: Use AI to find lookalike leads (and filter out bad fits) 🕵️♂️ 🔥 Step 2: Personalize outreach with the Triangle Method + pattern disruption 📩 🔥 Step 3: Show up prepared with AI-powered research & killer discovery questions 🧠 🔥 Step 4: Drive momentum with AI-generated recaps + creative follow-ups 🎥👀 This isn’t theory, it’s what elite sellers are already doing: ✨ Running account research with custom GPTs ✨ Crafting hyper-relevant outreach in minutes, not hours ✨ Closing more deals by standing out in a sea of generic sellers💥 Key takeaway: AI isn’t replacing sellers, it’s replacing unprepared sellers. If you’re still winging calls, you’re already behind.👉 Watch now to learn how to 10x your pipeline, quota, and win rate with AI.👉 JourneyAI: https://meetjourney.ai👉 Custom GPTs: https://skaled.com/services/sales-gpt...✉️ Subscribe to our newsletter: https://www.innovativeseller.com/ai-p...

Sep 10, 2025 • 46min
Stop Using Outdated Playbooks Like MEDDIC & BANT
Jake Dunlap, Founder and CEO of Scaled Consulting and author of The Innovative Seller, dives into the urgent need for sales leaders to update their approaches in the face of AI advancements. He discusses the limitations of outdated frameworks like MEDDIC and BANT, advocating for the Four C's and the VEX framework to personalize sales journeys. Dunlap highlights the importance of meaningful conversations over mere activity metrics, and introduces strategies like the 'magic email' technique for understanding buyer intentions better. His insights redefine how sales can align with modern consumer behavior.

Sep 3, 2025 • 27min
Breaking the Pattern: Why 90% of Sales Messages Fail
Chris reveals why your sales outreach isn't getting results: the shocking truth is that the bar for effective sales communication has never been lower. While most sellers obsess over volume and automation, they're missing what truly captures attention: pattern disruption.Studying the world's most persuasive communicators led Chris to develop "eloquence formulas" – strategic combinations of literary devices that make your messages impossible to ignore. Your brain filters out 90% of the patterns it encounters daily, which explains why most sales messages go unnoticed. The key to breaking through isn't just being different – it's being eloquently different.Dive into powerful rhetorical devices like anaphora (repeating words at successive beginnings), sententia (universal truths), and the rule of three that have influenced audiences throughout history. These aren't just academic concepts; they're practical tools that transform forgettable outreach into compelling communication. Watch as Chris demonstrates how to turn a generic email into three distinctive, high-impact messages using his formula approach.The conversation also explores how to leverage AI tools effectively by creating custom projects loaded with buyer persona details and prompting for specific literary frameworks. Unlike basic AI users who simply ask for generic outputs, sophisticated communicators push these tools to explore thousands of rhetorical devices and test combinations for maximum impact.What separates mediocre sellers from exceptional ones isn't just persistence – it's having a bold point of view. Too many sales professionals hide behind permission-based language instead of confidently presenting insights and solutions. Ready to elevate your sales communication? Start breaking patterns, embrace eloquence, and watch your response rates soar.

11 snips
Aug 20, 2025 • 46min
How OpenAI's Sales Reps Actually Use AI to Close Deals
Explore how revenue teams are transforming sales with generative AI, moving from experimentation to impactful applications. Learn about the essential role of AI fluency and personalized coaching through user guides. Discover how deep research capabilities streamline processes, turning hours of work into minutes. Successful executives sponsor AI initiatives, highlighting the importance of individual contributions to team and organizational success. Dive into the future where AI acts as an ever-present assistant, requiring sellers to adapt technically as they embrace these tools.

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/