The High Performance Sales Leader
"Actionable Insights from Inspiring Tech CROs & VPs" dives deep into the world of sales leadership within the dynamic technology sector.
Join us for 20-30 minute candid conversations with distinguished sales leaders—from nimble startups to global powerhouses—as they share their personal journeys, strategies, and secrets behind their remarkable results.
Whether you're an aspiring sales leader or a seasoned expert looking for fresh insights, this podcast offers a treasure trove of real-world wisdom, actionable takeaways, and lessons learned from the front lines of tech sales.
The High Performance Sales Leader
Ep 47: How Losing a $1M Deal Led to Achieving 29 President Clubs with Stephen Cottrell
Ever felt like you were doing everything right in a deal, only to lose it and realize you were never truly in the game? Or wondered how some reps consistently hit President’s Club like it's just another checkbox?
Stephen Cottrell doesn’t just hit quota. He’s earned 29 President’s Club awards over a 35-year career, closed over $1B in sales, and done it all across 48 countries. But it didn’t start that way. From boiling noodles in a Boston shoebox apartment to getting outflanked by IBM on a $1M deal, Stephen learned the hard way that grit, curiosity, and a process-driven mindset aren’t optional, they’re survival.
This episode isn’t about polished one-liners or LinkedIn fluff. It’s about what actually works: why MEDDIC changed his career, how to build resilience before you build pipeline, and the real reason being liked isn't enough. If you’ve ever wondered what separates the good reps from the elite, Stephen lays it all out. No filter, no fluff.
Let’s get into it.
Connect with Stephen Cottrell:
👉LinkedIn: https://www.linkedin.com/in/cottrell/
Connect with The High Performance Sales Leader Host:
👉LinkedIn: https://www.linkedin.com/in/preesarkar/
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