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AI-Powered Seller
Jake Dunlap
30 episodes
1 day ago
In a world where every seller is told to “automate everything,” how do you stay authentic? In this episode, host Jake Dunlap sits down with David Abbey, CEO and co-founder of Endless and Penny AI, to explore the future of human connection in a Gen AI-powered sales world. David was building AI solutions long before it became mainstream—helping sellers and creators strengthen relationships, not replace them. Together, Jake and David dive into what it really means to balance automation and authe...
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Business
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In a world where every seller is told to “automate everything,” how do you stay authentic? In this episode, host Jake Dunlap sits down with David Abbey, CEO and co-founder of Endless and Penny AI, to explore the future of human connection in a Gen AI-powered sales world. David was building AI solutions long before it became mainstream—helping sellers and creators strengthen relationships, not replace them. Together, Jake and David dive into what it really means to balance automation and authe...
Show more...
Business
Episodes (20/30)
AI-Powered Seller
Authenticity in the Age of AI
In a world where every seller is told to “automate everything,” how do you stay authentic? In this episode, host Jake Dunlap sits down with David Abbey, CEO and co-founder of Endless and Penny AI, to explore the future of human connection in a Gen AI-powered sales world. David was building AI solutions long before it became mainstream—helping sellers and creators strengthen relationships, not replace them. Together, Jake and David dive into what it really means to balance automation and authe...
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2 days ago
45 minutes

AI-Powered Seller
AI Maturity Part 2: The Road to AI-First Selling
Imagine logging in and your day is already in motion: target accounts analyzed, buyer signals surfaced, follow-ups drafted, and deal risks flagged—while you slept. That’s the reality we dive into as we map the jump from connected workflows to automated insights and, ultimately, an AI-first go-to-market hub where digital teammates handle the grind and you double down on the human edge. We start by grounding the maturity model: most teams sit in the Wild West or early assistant stages, with sc...
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1 week ago
21 minutes

AI-Powered Seller
AI Maturity Part 1: Getting Out of the Wild West
Most teams say they “use AI,” yet few can prove ROI. We dig into why that gap exists and lay out a practical roadmap any sales org can follow to move from ad hoc prompts to automated, connected workflows that save serious time and lift performance. We start by reframing generative AI as a foundational shift, not another tool in the stack. Then we map stages 0–3 of AI maturity. Stage zero is AI curious: lots of interest, little action. Stage one is the Wild West: tools without guardrails, inc...
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2 weeks ago
26 minutes

AI-Powered Seller
Personalization at Scale Isn’t Dead—You’re Doing It Wrong
Most sales teams don’t have an email problem—they have a relevance problem. Spray-and-pray activity chases quota while buyers tune out anything that doesn’t speak to their world. We bring on Brandon Bornancin, founder and CEO of Seamless AI, to unpack a simple but powerful fix: combine persona, industry, and trend to deliver outreach that earns attention, and use AI to get to version one faster without removing the human touch. We walk through a practical system you can deploy this week. Sta...
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3 weeks ago
45 minutes

AI-Powered Seller
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...
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1 month ago
17 minutes

AI-Powered Seller
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 h...
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1 month ago
26 minutes

AI-Powered Seller
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 ME...
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1 month ago
45 minutes

AI-Powered Seller
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...
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1 month ago
18 minutes

AI-Powered Seller
Stop Using Outdated Playbooks Like MEDDIC & BANT
We explore how the sales landscape is transforming with AI, requiring leaders to rewire their problem-solving approaches and update outdated methodologies with more effective frameworks like the Four C's. • Commitment to technology and AI proficiency is crucial for sales leaders to understand what's possible • Most revenue leaders have outsourced knowledge of tech capabilities to overwhelmed RevOps teams • The 80-15-5 principle helps leaders balance immediate business needs with future-focus...
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1 month ago
46 minutes

AI-Powered Seller
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 patter...
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2 months ago
26 minutes

AI-Powered Seller
How OpenAI's Sales Reps Actually Use AI to Close Deals
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, a...
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2 months ago
46 minutes

AI-Powered Seller
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 deal...
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4 months ago
19 minutes

AI-Powered Seller
‘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...
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5 months ago
25 minutes

AI-Powered Seller
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 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 ad...
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5 months ago
37 minutes

AI-Powered Seller
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. Di...
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6 months ago
24 minutes

AI-Powered Seller
How To Get 5X More Sales Meetings Using AI | ChatGPT For Outbound Prospecting Strategy
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 - ...
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6 months ago
28 minutes

AI-Powered Seller
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. ...
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7 months ago
21 minutes

AI-Powered Seller
3 Ways to Implement GenAI to 10X Your Sales Productivity
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 opt...
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7 months ago
16 minutes

AI-Powered Seller
Sam Altman’s AI Sales Bombshell: Did OpenAI just replace SDRs for good?
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 ...
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8 months ago
17 minutes

AI-Powered Seller
The 3 Skills Every Seller Needs to Survive the AI Shift
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” discu...
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8 months ago
30 minutes

AI-Powered Seller
In a world where every seller is told to “automate everything,” how do you stay authentic? In this episode, host Jake Dunlap sits down with David Abbey, CEO and co-founder of Endless and Penny AI, to explore the future of human connection in a Gen AI-powered sales world. David was building AI solutions long before it became mainstream—helping sellers and creators strengthen relationships, not replace them. Together, Jake and David dive into what it really means to balance automation and authe...