AI-Powered Seller

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 o...

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 ris...

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 reflect...

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 hol...

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 sa...

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...

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-b...

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...

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 he...

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 con...

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 ti...

🔥 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 opera...

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 co...

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 r...

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...

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 cur...

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 wi...

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...

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...

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 incr...

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) 🕵️‍♂️  🔥 Ste...

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 overwhe...

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" – strateg...