AI-Powered Seller

• Authenticity in the Age of AI

  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.

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• 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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• AI Maturity Part 1: Getting Out of the Wild West

  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.

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• 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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• 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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