AI-Powered Seller
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...
Emotional Intelligence vs. AI: What's Actually Winning Outbound Right Now
AI is everywhere in sales right now, and that’s exactly why sounding human has become a competitive advantage. Jake Dunlap sits down with Kelly Lichtenberger, VP of Sales Development at Silverfort and author of Prospect Like a Girl, to get real about EI versus AI and why “outsourcing” emotional intelligence is a fast way to lose trust on the phone. If your outreach is starting to feel generic, scripted, or weirdly identical to everyone else’s, this conversation will hit close to home.
Connect with Kelly on LinkedIn.
The Non-Linear Buyer Journey: How Top Performers Adapt and Win
Steal This AI Prompt And 10x Your Sales In 30 Days
AI GTM Pulse Debrief
Skaled’s AI GTM Pulse survey was conducted in April 2026 to understand how GTM teams are using and operationalizing AI.
In this debrief, I bring those insights together, connecting the dots across usage, automations, ownership, and measurement. The debrief reframes AI as GTM integration and shows what it takes to move from never-ending experimentation loops to real impact.
Hear the current pulse on AI in GTM. Not adoption, not how many hours saved, not doing more with less… a pulse on how AI is actually showing up in processes and workflows. Realize the delta...From Zero To AI-Ready Leadership
Still feeling stuck at step zero with AI—lots of prompts, no real leverage? We walk through five concrete moves that flip AI from novelty to advantage for frontline sales leaders and ambitious sellers. It’s a fast, tactical tour: onboarding that compresses ramp, a coaching memory that never forgets, development plans that stick, a leader-specific GPT that encodes your standards, and a pipeline risk radar that tightens forecasts without more meetings.
We start by rebuilding onboarding so reps get high-quality “at bats” in week one. By training an assistant on your ICPs, buyer personas, and competitor position...
Why AI Should Support Your Interviews, Not Replace Them
Tired of gut calls and keyword roulette deciding who joins your team? We sat down with Chrissy Manzano, CEO of Blueprint Expansion, to map where AI actually improves hiring today—without pretending it can replace thoughtful human judgment. From SDRs and BDRs to manager and director roles, we break down how to speed up sourcing, standardize interviews, and create a candidate experience that reflects your brand.
We start with sourcing, where legacy tools cling to keywords and miss context. Chrissy shows how to encode practical criteria—real SaaS exposure, tenure stability, and proof of growth journeys—to help A...
Why Every CRO Must Learn AI Or Get Left Behind
What happens when a seasoned CRO decides to stop “exploring” AI and actually master it? We sit down with Colin Van Excel to chart the path from a single prompt that wrote a price increase letter to a full, AI-first sales operating system. The story is practical, candid, and packed with takeaways you can use today, whether you lead a revenue org or carry a quota.
We start with the real barriers holding teams back: fuzzy sales processes, inconsistent stage criteria, and sellers buried in admin. Colin explains how he rebuilt around the buyer’s journey, then layere...
A 2025 AI Reality Check for Sales Leaders, Reps, and RevOps
What happens when you stop predicting the future and actually audit the past?
In this episode of AI Powered Seller, Jake Dunlap revisits his 2025 AI predictions and gives them an honest scorecard. No hype. No backpedaling. Just real lessons from the front lines of revenue teams adopting AI.
Co-hosted by Skaled’s Head of Marketing Kara Burd, this conversation breaks down how AI really impacted sales teams over the last year and why some widely held assumptions completely missed the mark.
You will learn:
• Why reps adopt...
Why AI’s Real Power Lives in Pre-Sales and Not Prospecting
Most AI in sales content is stuck at the top of funnel: prompts, prospecting, and research.
This episode is different.
Jake Dunlap sits down with David Maloof, Founder and Managing Partner of Pre-Sales Advisory Group and longtime pre-sales leader across high-growth SaaS and enterprise orgs, to unpack a truth most teams miss:
AI’s real power shows up in pre-sales, where discovery, storytelling, and demos decide whether you win or lose.
David breaks down how the best SEs and revenue teams are using AI to:
show up to discovery with a...Top 5 AI Predictions That Will Separate Top Sales Teams in 2026
2026 is the year AI stops being optional in sales.
In this episode of AI Powered Seller, Jake Dunlap walks through his five biggest AI predictions for 2026 — and why sellers and leaders who don’t act now will be forced to catch up later.
This conversation goes beyond tools and trends. Jake explains how AI becomes a true go-to-market teammate, why generic personalization is dead, and how signal-based selling will redefine outbound, deal cycles, and account growth.
You’ll learn:
What digital teammates actually look like in modern...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 bottleneck, then choose technology that solves it.
Innovative Seller
You’ll also get J...
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, improves win rates, and enables managers to coach more effectively.
In this episode, we cover:
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 use automation to surface coaching opportunities, review call quality, and improve overall team performance without hours of manual an...
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 can take on multi-step work across research, deal strategy, enablement...
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 organizations — and what high-performing teams do differently to turn AI into a true competitive advantage.
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 walks through a tactical, play-by-play guide of how AI is changing every step of...
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 authenticity, where AI adds value (and where it destro...
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 scattered tools and no roadmap. Then we show how stage four flips the script. Instead of w...
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, inconsistent results, and off-brand outputs. Stage two introduces emerging assist...
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. Start by obsessing over personas: goals, KPIs, constraints, and dream outcomes. Add an indust...
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...
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...
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...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 the...
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-focused development
• Current go-to-market strategies must evolve beyond outdated frameworks like Predictable Revenue
• Today's outbound approach should focus on meaningful conversations, not just activity metrics
• Cust...
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...
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, 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 member...
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...
‘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...
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 adding unique value.
Sean, who advises hundreds of PE firms and their portfolio companies on AI...
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.
Discover how to decode subtle buyer signals, identify true priorities, and catch objection precursors before they derail your deals. I'll reveal...
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
- How to generate custom podcast episodes about your prospect's business in 10 minutes
- Why "automated" killed effectiveness...
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.
Data security & privacy – Why fears from 2023 are holding companie...
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 optimize your workflow
Process automation – Why scaling efficiency isn’t about replacing humans, but working smarter
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 with Jake’s unfiltered reaction to all that th...
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” discussion. Instead of his usual co-host, KD, Jake is joined by a different kind of guest...
Should Sales Teams be Worried? What Generative AI Means for Marketing and Product Teams
This episode explores how generative AI is transforming marketing and product development, emphasizing its potential to drive creativity and optimize strategies while underscoring the necessity of human oversight. Listeners gain valuable insights on leveraging AI for impactful copywriting, marketing analysis, and product innovation.
• Generative AI's role in writing compelling website copy and product descriptions
• Emphasizing the power of testing and learning in marketing strategies
• AI's ability to enhance emotional engagement in content creation
• The need for data-driven decision-making in marketing practices
• The interplay of human creativity and AI in product innovation
• Bridging the gap betw...
Building Knowledge Documents & Using ChatGPT Memory Effectively
Explore the latest advancements in Generative AI, from Custom GPTs to knowledge documents, and how they can transform productivity in sales and beyond. Gain insights into practical applications and features, while discovering new tools to enhance efficiency.
• Overview of AI trends impacting sales
• Introduction to Claude
• New features in the ChatGPT app, including voice interaction
• Benefits and implementation of custom GPTs
• Discussion on knowledge documents and their advantages
• Overview of ChatGPT’s memory functionality
• Tips for maximizing LinkedIn insights with AI
Sign up for the newsletter for free resources on AI trends and...
Why Revenue Teams Are Seeing 0.00 Value in Generic AI Implementations
Can generative AI truly revolutionize sales, or is customization the secret ingredient to success? Uncover the transformative potential of custom AI models as we explore the pivotal role of data quality in deriving meaningful value from AI implementations. Many teams struggle to see results when applying AI generically; our discussion sheds light on the importance of tailoring AI models to fit your unique business landscape. From understanding sales playbooks and buyer personas to recognizing when to choose custom models over plug-and-play solutions, we promise you'll gain insights into maximizing your AI investments.
Witness firsthand how small, continuous...
Harnessing AI for Dynamic Sales Scenarios
This episode dives into the transformative potential of generative AI in sales training, focusing on how it can enhance role-playing exercises for sales reps. We discuss practical applications, share insights from real-world experiences, and highlight how to effectively integrate AI into sales processes for skill building.
- Discuss the advantages of using generative AI for role-playing in sales training
- Explore the concept of memory in AI tools and how it aids learning
- Share survey results on the current usage of AI for role-playing among sales professionals
- Emphasize the importance of foundational...
