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 sales workflows
• Why AI-generated personalization alone won’t cut through
• How coaching shifts from post-call to real-time execution
• Why signal-based selling becomes mandatory, not optional
• Why AI fluency becomes table stakes in 2026

If you want to win in sales next year, this episode is required listening.

Learn more about Skaled: https://www.skaled.com

Connect with Jake on LinkedIn: https://www.linkedin.com/in/jakedunlap/

Check out Journey AI: http://meetjourney.ai/

AI Certification for Reps: https://bit.ly/ai-sales-certification-rep

AI Certification for Managers: ​​https://bit.ly/ai-sales-certification-manager

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 Jake’s tactical seller playbook for adopting GenAI in a sustainable way:

• Identify your three most painful tasks
• Refine AI outputs so they sound like you
• Build a simple ongoing roadmap so you don’t try to solve everything at once

Check 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 2026

If 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 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.