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Owner-led sales can feel like freedom until you realize you’re capped by your own calendar. Morris Sims sits down with Greg, a fractional Chief Revenue Officer and longtime high-tech sales leader, to unpack why so many B2B founders stall around the $2M to $3M mark and what it actually takes to build a sales organization that runs without you doing everything. We get concrete about the difference between “hoping” for growth and installing a process, accountability, and a pipeline that tells the truth.

Then we go deep on AI in sales with practical use cases you can try immediately. Greg walks through how AI speeds up account research by summarizing annual reports and company priorities, how it improves pre-call planning with smarter discovery questions and objection prep, and how call transcripts can be scored against a coaching rubric like BANT, MEDDICC, or SPIN. If you’re coaching a team with limited time, this transcript-to-rubric workflow can spotlight weaknesses fast and keep feedback specific instead of emotional.

We also talk about the messy side of AI adoption: shiny tool chasing, shadow AI, and what happens when seven reps use 11 tools that don’t connect to the CRM. From CRM resistance to forecasting fantasy, we share how to drive real adoption, why HubSpot often wins on usability, and how pipeline stages with required exit criteria replace “it feels like an 80% deal.” Finally, Greg explains why the classic BDR model is struggling, why targeted prospecting around trigger events performs better, and how LinkedIn Sales Navigator helps you find the right moment to reach out.

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