AI-Powered Seller

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 SellerYou’ll also get Jake’s tactical seller playbook for adopting GenAI in a sustainable way:Identify your three most painful tasksRefine AI outputs so they sound like youBuild a simple ongoing roadmap so you don’t try to solve everything at onceCheck Out: JourneyAI (free trial): https://meetjourney.ai/Jake Dunlap – https://www.linkedin.com/in/jakedunlap/Skaled - https://skaled.com/If you got value from this episode, share it with a teammate in Sales, RevOps, Enablement, or Marketing, and make sure you’re subscribed so you don’t miss the next drop.

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: • Why traditional forecasting models fail • Which AI signals improve top-of-funnel accuracy • How to identify hidden deal risks with AI • Why deal reviews are the first workflow leaders should automate • A new way to think about pipeline coverage • The mindset shift every sales leader must make in 2025 • What predictable revenue will actually look like by 2026If you’re a frontline rep, manager, or revenue leader looking to drive predictable revenue and adopt AI the right way, this episode will give you one clear takeaway you can act on today.

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 analysis.What you’ll learn: • How AI can complete account research, intent scoring, and meeting prep automatically • How follow-ups, summaries, and CRM activity can be fully automated • How top sellers optimize outbound using real-time performance insights • Practical examples of digital teammates that improve deal execution • How modern leaders use AI to scale coaching and increase visibilityLinks from the episode: 👉 JourneyAI: https://meetjourney.ai/👉 Performance Pulse: https://www.revoptics.co/services/sales-reporting👉 Superhuman: https://superhuman.com👉 AI Sales Training & Certifications for GTM Teams: https://skaled.com/services/ai-sales-training/Connect with Us: https://www.linkedin.com/in/jakedunlap/https://www.linkedin.com/company/skaled/ https://skaled.com/

Ryan Staley, Founder and CEO of Whale Boss, shares how AI can transform sales roles into more efficient units. He emphasizes the shift from viewing AI as a simple tool to treating it as a digital teammate that can handle multi-step tasks. Ryan explains the importance of creating tailored AI assistants like deal strategy and account research. He also addresses common barriers to AI adoption and strategies to present AI effectively to drive engagement. Finally, he urges leaders to retrain teams urgently to stay competitive in this evolving landscape.

🔥 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.He reveals the tactical playbook that top teams use to improve outbound, accelerate deal cycles, and make reps instantly smarter using AI.🔥 What you'll learn in this episode (Don't miss the real truth behind AI!):✨ The Core Problem: Why companies expect AI to be a magic wand — and why that mindset guarantees failure.🧠 The Setup Mistake: The missing pre-work every team skips that destroys ROI before AI ever launches.⚙️ Human-in-the-Loop: How elite teams combine rep judgment + AI to outperform both humans and automation alone.📈 Outbound Breakthroughs: Why AI now outperforms template-based SDR outreach — and how reps can stay relevant.🔍 Instant Expertise: How reps can now learn any industry in 10 minutes and run world-class discovery.🏆 The GTM Advantage: How AI lets leaders analyze their business, pivot faster, and double down on what actually works.This isn’t about more tools — it’s about better strategy, better execution, and smarter humans using AI the right way.👉 Tune in and learn how to become a modern, AI-powered, outcome-driven seller!

Explore how AI is revolutionizing the daily workflow of sales professionals. Discover tools like RepGPT and Journey that streamline research and automate tedious tasks. Learn to craft personalized outreach through advanced automation techniques. From pre-call prep to targeted follow-ups, hear how AI enhances productivity while promoting meaningful conversations. Dive into the shifts that separate traditional sellers from AI-savvy peers and get practical tips for transforming your sales day for better results.

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 destroys it), and why being “more human” might just be your ultimate competitive advantage in 2025 and beyond.You’ll learn:How AI can surface insights to make your interactions more personal and meaningfulThe red flags of “too much automation” and how to avoid losing your human touchWhy the future belongs to sellers who master context and creativityHow influencer marketing and digital avatars are reshaping trust and communicationWhether you’re a rep looking to up your game or a leader rethinking your team’s AI strategy, this episode is packed with real talk, tactical advice, and future-forward insights.Tune in to learn how to use AI to amplify authenticity—not replace it.

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 waiting for prompts, your AI scouts LinkedIn updates from key buyers, ingests annual reports, compares year-over-year changes, and suggests targeted actions with one-click approvals. For managers, we go beyond checkbox scorecards to true deal intelligence: auto-scored calls, focused coaching on executive presence or financial acumen, and Slack nudges that cut through the noise so you can coach where it counts.From there, we pull back the curtain on stage five: AI as the operating system for revenue. Reps log into the AI hub before the CRM. Overnight, a network of digital teammates researches accounts, composes context-rich outreach, syncs notes, and builds a morning brief. Marketing adjusts campaigns based on live pipeline signals. Leaders stop asking the same 20 questions and start acting on precise recommendations with clear guardrails. We outline how to get unstuck—assign owners, ship small wins weekly, codify what “good” looks like, and train reps and managers to build lightweight agents—so adoption grows from the front lines and compounds.If you’re ready to trade busywork for real conversations and build a moat your competitors can’t buy off the shelf, this guide lays out the path. Subscribe, share with your team, and leave a review telling us which task you’ll hand off to your first digital teammate.

Discover the reality behind AI adoption in sales, where many teams claim to utilize it but struggle to demonstrate real ROI. Explore the journey from being AI curious to navigating the chaotic Wild West of ad hoc tools. Learn how emerging assistants can streamline tasks like call reviews and account research, saving teams dozens of hours monthly. Dive into the potential of connected workflows that automate processes, transform transcripts into proposals, and simplify CRM updates. Gain insights on assessing your AI maturity and actionable steps to enhance efficiency.

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 industry lens to reflect real differences between SaaS, manufacturing, finance, and healthcare. Layer current trends—labor markets, tech stack shifts, budget cycles—to show you understand what’s changing right now. Then put AI to work: build rich profiles from job postings and public data, enrich accounts with signals like job changes and funding, and generate first-draft emails and call scripts with tight prompts that skip fluff and get to the point. Keep a human in the loop to edit for tone and truth, and use discovery that blends open-ended questions with multiple-choice options to surface priorities quickly.Brandon shares how Seamless AI helps teams move “data to deals,” automating the invisible work—list building, enrichment, and drafting—so reps can focus on high-value conversations. We dig into why scale doesn’t mean full automation, how to avoid AI’s telltale patterns by swapping models and editing, and the skills that now matter most: curiosity, strategic thinking, and empathy. If you’re tired of 0.02% reply rates and want a playbook for high-quality meetings, this conversation lays out the path: persona-first, industry-aware, trend-informed, and AI-accelerated.Enjoyed the conversation? Follow, share with a teammate who needs a new outbound playbook, and leave a quick review with your biggest takeaway. Your feedback helps us bring more tactical, high-signal conversations to your feed.