The best way to learn sales has always been the same: sit next to someone good and listen to how they actually work a deal. Most of us never get that shot. Consider this yours. The good, the bad, and the ugly.
Three lanes: how I broke into sales, tactical coaching for reps who are stuck, and where AI actually helps in the day to day. Filter below.
The gap between onboarding and actually knowing what you're doing.
PlannedMoving from telecom to SaaS meant relearning half of what I thought I knew.
PlannedThe framework in plain English, no textbook jargon.
PlannedWhat my UNM students get wrong the first time they try it live.
PlannedThe actual prompts and workflow, not just "use ChatGPT."
PlannedThe parts of the job it can't do for you, and probably shouldn't.
Planned3.5 years at Comcast Business. Hit quota 38 of 39 months. I made President's Club twice.
Now I run SMB deals at HubSpot, $10K to $130K in ARR. MEDDICC certified. Aiming for mid-market next.
On the side, I coach UNM's sales competition team. SPIN and BANT, taught to people who've never carried a quota. This newsletter is that same coaching, just written down.
“Simon taught me more about sales and being a professional in four weeks than I'd learned in the past two years.
“Simon is so generous with what he's learned, always giving real actionable advice rather than generic sales talk.
“Simon isn't just focused on his own goals. He's deeply invested in the success of his team and colleagues.
“Simon proved to be a role model early on, consistently overdriving his quota as a top performer nationwide.
“Simon finished in the top 5% of account executives nationwide, closing out 2024 as the #9 sales rep in the country.
“Simon is a multiple-year President's Club winner. Being around him made me better, professionally and personally.
“Simon spent countless hours showing me the ropes, coaching me on calls, and helping me build for the future.
“Simon coached me for the National Collegiate Sales Competition. An incredible, kind leader who I learned so much from.
“Simon taught us real-world sales and what it actually takes to succeed beyond the classroom.
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