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 visibility

Links 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/

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, and leadership workflows.

In this conversation, you’ll learn:
✅ The difference between a prompted assistant vs. a true digital teammate
✅ The top AI teammates to build first (account research, next-best-action, deal strategy)
✅ Why AI “liberates intelligence” and how to avoid the AI pit of despair
✅ What’s really holding sales orgs back from adoption (overwhelm + no top-down sponsorship)
✅ How to talk ROI in a way CFOs actually buy
✅ What’s coming next: agent orchestration, Cursor 2–style multi-agent management, and everyone becoming an “AI manager”

Whether you’re a rep trying to level up fast or a leader redesigning roles for the AI era, this episode will help you move from AI curiosity to AI execution.

👉 Subscribe for weekly episodes with real GenAI sales use cases.
⭐ If you got value, drop a comment: what digital teammate would save you the most time this week?
📩 Share this with one sales leader or rep who needs a 2-year edge.

Connect with us:
Jake Dunlap on LinkedIn: https://www.linkedin.com/in/jakedunlap/
Ryan Staley on LinkedIn: https://www.linkedin.com/in/ryan-staley/

Skaled: https://skaled.com/
Whale Boss: https://ryanstaley.io/


#AIPoweredSeller #SalesAI #GenerativeAI #SalesLeadership #DigitalTeammates

🔥 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!

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 the sales day. You’ll learn:

• What an AI powered day really looks like and how it differs from the old Google and LinkedIn grind
• How to use tools like RepGPT, Journey, and Outbound Meeting Co-Pilot to prep faster and sell smarter
• Why automations and assistants, not just prompts, are the real edge in modern sales
• The small daily habits that separate traditional sellers from their AI enabled peers

If you’ve ever felt buried under research, logging, and admin work, this episode will show you how to turn those hours into impact.

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 meaningful
• The red flags of “too much automation” and how to avoid losing your human touch
• Why the future belongs to sellers who master context and creativity
• How influencer marketing and digital avatars are reshaping trust and communication

Whether 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.

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 assistants—specialized AI that handles repeatable jobs like account research, messaging co-pilots, call reviews, and deal strategy. Finally, stage three connects those assistants into end-to-end workflows that trigger on real events: calendar invites that auto-generate dossiers, transcripts that draft proposals, and notes that update the CRM with zero manual effort.

Along the way, we share concrete examples and time-saved math that translate to real headcount efficiency—think sixty-plus hours reclaimed per month on a 20-rep team. You’ll hear how to pick the first bottleneck, standardize use cases, build or adopt assistants, and stitch them together with no-code and low-code tools in weeks, not quarters. We also include a quick checklist to self-assess your current stage and define the next step, whether you’re a frontline seller, a manager, or a VP building the roadmap.

Ready to trade copy-paste chaos for measurable impact? Subscribe, share this with your team, and leave a review to tell us which assistant or workflow you’ll build first. Your feedback helps us shape part two, where we explore the next levels of AI maturity and scale.

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.