Is AI Quietly Breaking Your Annual Planning? A GTM Midyear Check

<p>TLDR: Eight months into 2026, Kelly Lewis and Tiffany Jones put their January predictions on trial. AI isn&#39;t coaching your reps, most companies aren&#39;t running the agents they told their board about, and annual planning is about to get messy.</p><p><br></p><p>Season 3 of The Revenue Insiders opens with a midyear reckoning. Kelly and Tiffany revisit the go-to-market predictions they made in January and test them against what is happening now: sales manager span of control creeping toward 15 reps, SDR promotions falling off a cliff, the gap between companies that have deployed AI agents in RevOps and the ones that just say they have, and consumption pricing hitting annual plans nobody built for it. </p><p><br></p><p>They also get into the Seismic and Highspot merger, what an OpenAI hiring post and the EU ban on emotion recognition in hiring tools say about EQ in sales, plus why governance is still unsolved in revenue operations. If you lead sales, RevOps, or enablement, or you are early in your sales career, this is your 2027 planning prep.</p><p><br></p><p>In this episode:</p><ul><li>Why AI coaching inside the tools isn&#39;t the same as a manager developing a rep, and what happens when finance plans for 15 reps per sales manager</li><li>The RevOps &quot;haves and have nots&quot; of AI agents, and why so many boards are being told a story that isn&#39;t true</li><li>How AI assisted annual planning goes wrong when it&#39;s built on bad data and ignores the people, the buyer, and the go-to-market reality</li><li>What consumption and outcome based pricing mean for comp plans, forecasting, net dollar retention, and the role of the CSM</li><li>The future of enablement after the Seismic and Highspot merger, and why cutting your enablement team for AI is the wrong ROI math</li><li><br></li></ul><p>Follow The Revenue Insiders wherever you listen and leave us a rating. It helps more GTM professionals find the show.</p>