If It Was Easy, Everyone Would Do It: AI Strategy for GTM Leaders

<p>Jeff Rosset didn&#39;t just start using AI tools. He built an internal system of AI employees inside Claude that do specialized work for his business. The way he got there is a masterclass in how to actually adopt AI without losing what makes human revenue teams irreplaceable.</p><p>Jeff Rosset is the founder of Sales Assembly, a peer community for revenue leaders at some of the fastest-growing B2B tech companies in the country. He&#39;s spent over 20 years in B2B sales and has a front-row seat to what&#39;s working, what&#39;s failing, and what most leaders won&#39;t admit isn&#39;t working.</p><p>In this episode, Jeff breaks down how he approaches AI as infrastructure. He built hyper-specific AI personas — a customer marketing expert, a strategic advisor, a pressure-tester — and stitched them into a collaborative system that elevates every project he runs. The foundation came first. The speed and quality of output came after.</p><p>He also shares something most AI conversations skip: the discipline required to get the most out of these tools. Pushing back when the AI tells you what you want to hear. Running your Claude-built plan through a NotebookLM critique. Returning to your desk with notes and iterating again. It&#39;s a loop. And it works because Jeff treats it like one.</p><p>If you&#39;re a revenue leader trying to figure out what AI adoption should actually look like — not what LinkedIn says it should look like — this is the episode.</p><p><strong>In This Episode:</strong></p><ul><li>The AI employee framework Jeff built and how it mirrors a real team dynamic</li><li>Why LinkedIn is becoming a minefield of AI slop and how to protect your personal brand</li><li>What enablement leaders are rightly doubling down on in a world of AI-assisted reps</li><li>The outdated playbooks still running in too many GTM orgs</li><li>Jeff&#39;s honest take on where AI impacts services companies vs. software companies differently</li></ul><p>Follow The Revenue Insiders and leave us a rating, it helps more GTM professionals find the show.</p><p>Connect with Jeff Rosset: <a href="https://www.linkedin.com/in/jeffrosset">https://www.linkedin.com/in/jeffrosset</a> | salesassembly.com</p>