AI-Powered Seller

Jake Dunlap
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Oct 29, 2025 • 22min

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 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.
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Oct 22, 2025 • 26min

AI Maturity Part 1: Getting Out of the Wild West

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.
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Oct 15, 2025 • 46min

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 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.
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Oct 8, 2025 • 18min

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 orchestrator that checks Salesforce, enriches with public insights, drafts a reply, and summarizes in Slack; a deal health sentry that monitors engagement, multithreading, and silence windows, then escalates with context; and a proposal producer that pulls your last call, maps to your statement-of-work template, asks clarifying questions, and outputs a Google Doc v1. Along the way, I share a story from my early career about finding conversion “quiet pockets” and how the same insight now takes thirty minutes to automate end-to-end.There are guardrails: keep the human touch for tone and senior outreach, expect occasional connector changes, and invest time upfront to define quality. But the upside is real and immediate—sellers who learn agents can 2–3x output and build compounding advantage. If you’ve ever felt buried in follow-ups, prep, and proposals, this is your way out through orchestration, not hustle theater. Subscribe, share this with your team, and tell me the first workflow you’ll automate. And if you want hands-on help, join our AI certification and leave with working agents and a repeatable playbook.
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Oct 1, 2025 • 26min

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. You’ll hear how a “New Account Research” teammate can scrape signals and context before you even open your CRM, how a pricing-objection specialist can produce competitor-aware responses in seconds, and how manager-trained GPTs can review call transcripts and give targeted coaching using your actual playbook. Then we zoom out and show what happens at the agent level: calendar-triggered prep, Slack clarifications, automated recaps, and draft SOWs that land in your docs without you lifting a finger. The numbers are real—a 47% productivity lift, roughly 12 hours a week back—translating into more selling time, better personalization, and cleaner pipelines.If you’re at level one, we lay out a fast track to level three: convert your best prompts into assistants, feed them product and persona context, and standardize outputs so quality is consistent. Leaders get a roadmap to become multipliers by setting a GenAI backlog, prioritizing high-impact workflows, and rolling out shared assistants across the team. Hiring is already shifting; candidates who can show live AI workflows will outrun those who “know ChatGPT.”If this guide helps, subscribe, share it with a teammate, and leave a review so more sellers find it. Want to level up faster? Explore the AI certification for sellers and frontline leaders, and test-drive the MeetJourney assistants tailored for sales teams.
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Sep 24, 2025 • 46min

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 use AI for scenario planning and competitive intelligenceThe difference between hierarchy and "powerarchy" in modern dealsWhy 95% of buying happens without you — and how to influence itTactical frameworks for accommodating vetted, educated, and self-service buyersKey Takeaway: The future belongs to sellers who deliver "buying process as a service" — becoming an extension of the buyer's team rather than an obstacle to navigate.Check out: The Innovative Seller: https://a.co/d/cbh8hM3JourneyAI: https://meetjourney.aiSubscribe: New episodes every week on your favorite podcast platform. Leave a review on Apple Podcasts to help us reach more sales professionals.Remember: AI won't replace sellers — sellers who know how to use AI will replace those who don't.
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Sep 17, 2025 • 18min

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 theory, it’s what elite sellers are already doing: ✨ Running account research with custom GPTs ✨ Crafting hyper-relevant outreach in minutes, not hours ✨ Closing more deals by standing out in a sea of generic sellers💥 Key takeaway: AI isn’t replacing sellers, it’s replacing unprepared sellers. If you’re still winging calls, you’re already behind.👉 Watch now to learn how to 10x your pipeline, quota, and win rate with AI.👉 JourneyAI: https://meetjourney.ai👉 Custom GPTs: https://skaled.com/services/sales-gpt...✉️ Subscribe to our newsletter: https://www.innovativeseller.com/ai-p...
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Sep 10, 2025 • 46min

Stop Using Outdated Playbooks Like MEDDIC & BANT

Jake Dunlap, Founder and CEO of Scaled Consulting and author of The Innovative Seller, dives into the urgent need for sales leaders to update their approaches in the face of AI advancements. He discusses the limitations of outdated frameworks like MEDDIC and BANT, advocating for the Four C's and the VEX framework to personalize sales journeys. Dunlap highlights the importance of meaningful conversations over mere activity metrics, and introduces strategies like the 'magic email' technique for understanding buyer intentions better. His insights redefine how sales can align with modern consumer behavior.
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Sep 3, 2025 • 27min

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 into powerful rhetorical devices like anaphora (repeating words at successive beginnings), sententia (universal truths), and the rule of three that have influenced audiences throughout history. These aren't just academic concepts; they're practical tools that transform forgettable outreach into compelling communication. Watch as Chris demonstrates how to turn a generic email into three distinctive, high-impact messages using his formula approach.The conversation also explores how to leverage AI tools effectively by creating custom projects loaded with buyer persona details and prompting for specific literary frameworks. Unlike basic AI users who simply ask for generic outputs, sophisticated communicators push these tools to explore thousands of rhetorical devices and test combinations for maximum impact.What separates mediocre sellers from exceptional ones isn't just persistence – it's having a bold point of view. Too many sales professionals hide behind permission-based language instead of confidently presenting insights and solutions. Ready to elevate your sales communication? Start breaking patterns, embrace eloquence, and watch your response rates soar.
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11 snips
Aug 20, 2025 • 46min

How OpenAI's Sales Reps Actually Use AI to Close Deals

Explore how revenue teams are transforming sales with generative AI, moving from experimentation to impactful applications. Learn about the essential role of AI fluency and personalized coaching through user guides. Discover how deep research capabilities streamline processes, turning hours of work into minutes. Successful executives sponsor AI initiatives, highlighting the importance of individual contributions to team and organizational success. Dive into the future where AI acts as an ever-present assistant, requiring sellers to adapt technically as they embrace these tools.

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