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AI-Powered Seller

Jake Dunlap

36 episodes

1 week ago

AI Bubble or Breakout: Are you building real, needle-moving workflows with AI, or collecting “bubble” use cases that create overlap and extra change management? In this episode of AI Powered Seller, Jake Dunlap explains why the “AI bubble” is not AI itself, but the noise on top of it, including duplicate tools, overlapping features, and organizations investing without clear ownership. He breaks down how GTM leaders and frontline sellers can evaluate AI the right way: start with the revenue bo...

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AI Bubble or Breakout: Are you building real, needle-moving workflows with AI, or collecting “bubble” use cases that create overlap and extra change management? In this episode of AI Powered Seller, Jake Dunlap explains why the “AI bubble” is not AI itself, but the noise on top of it, including duplicate tools, overlapping features, and organizations investing without clear ownership. He breaks down how GTM leaders and frontline sellers can evaluate AI the right way: start with the revenue bo...

Show more...

Episodes (20/36)

AI-Powered Seller

AI Bubble or Breakout: The Reality of AI in Sales

AI Bubble or Breakout: Are you building real, needle-moving workflows with AI, or collecting “bubble” use cases that create overlap and extra change management? In this episode of AI Powered Seller, Jake Dunlap explains why the “AI bubble” is not AI itself, but the noise on top of it, including duplicate tools, overlapping features, and organizations investing without clear ownership. He breaks down how GTM leaders and frontline sellers can evaluate AI the right way: start with the revenue bo...

1 week ago

20 minutes

AI-Powered Seller

Why Forecasting Fails — And How AI Fixes It

In this episode, Jake is joined by revenue leader Chris Casula for a highly tactical conversation on how AI is transforming pipeline management, forecasting accuracy, and GTM productivity. Chris shares hard-won insights from managing enterprise and transactional sales teams, and breaks down why forecasting has historically been the “bane of sales” — and why it’s not the reps’ fault. You’ll also hear real examples of how AI surfaces buying signals, identifies bottlenecks in the sales process, ...

2 weeks ago

42 minutes

AI-Powered Seller

AI in Sales, Part 2: How to Automate and Scale Your Daily Workflow

In Part 2 of our AI in Sales series, Jake Dunlap breaks down how top sellers are moving from basic AI assistance to fully automated workflows that run before, during, and after their workday. This episode shows how modern reps are scaling their daily workflow using automation that handles research, meeting prep, intent analysis, follow-ups, and CRM updates—freeing them to focus on higher-value conversations. Jake also explores what AI-enabled leadership looks like today, and how managers can ...

3 weeks ago

21 minutes

AI-Powered Seller

How Top SaaS Reps Use AI Digital Teammates to Win More Deals in 2026

In this episode of The AI-Powered Seller, Jake Dunlap sits down with Ryan Staley (Founder & CEO of Whale Boss) to break down the 2026 AI mindset shift every CRO, VP Sales, and frontline rep needs right now. If you’re being asked to do more with less, increase personalization, and keep pipeline moving in a noisy market, this is your tactical playbook. Ryan and Jake go beyond basic “prompting tips” and show how to train AI like a digital teammate — not a tool you poke for answers — so it c...

1 month ago

39 minutes

AI-Powered Seller

Why Most AI Deployments Fail — And How Elite Teams Actually Win

🔥 Why Most AI Deployments Fail (And How Real Sellers Win With It) 🤖 Is AI actually helping sales teams — or just creating more noise? Why are so many companies struggling to get ROI from their AI investments? The brutal truth: it's often caused by broken processes, bad expectations, and outdated leadership. 😬 In this episode, Jake is joined by Ryan Cahill, a veteran GTM architect and operator who has helped scale revenue teams across SaaS. Ryan breaks down exactly why AI fails in most organi...

1 month ago

28 minutes

AI-Powered Seller

AI in Sales, Pt 1: How to Build an AI Powered Sales Day

In this episode of The AI Powered Seller, host Jake Dunlap, CEO of Skaled and co-founder of Meet Journey and Rev Optics, takes you inside the daily workflow of a modern AI powered sales professional. Jake breaks down how today’s top reps are transforming their routines using assistants, agents, and automation to reclaim hours of lost productivity and focus on what really matters: high quality conversations that close deals. From pre-call research to follow-up emails and social selling, Jake w...

1 month ago

24 minutes

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...

1 month 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...

1 month 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...

2 months 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...

2 months 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...

2 months 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...

2 months 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...

3 months 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...

3 months 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...

3 months 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...

3 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...

4 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...

6 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...

7 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...

7 months ago

37 minutes