E47: How Losing a $1M Deal Led to Achieving 29 Presidents Clubs with Stephen Cottrell

Timestamps:

00:00 29 Clubs, 35 Years, $1B+ in Sales

01:01 Tennis, Tension & Toughness

03:20 Sales Is the Hardest Job in the World

04:20 Noodles, Rats & Hustle in Boston

06:50 The $1M Deal That Got Away

09:30 Discovering MEDDIC & the Power of Methodology

10:45 The Traits of High Performers

12:40 Trust the Process: Nick Saban’s Influence

About Stephen Cottrell

Stephen Cottrell is the Director of the Asian Pacific Region at Alation, For over three decades, Stephen Cottrell has been selling at the highest levels—earning 29 President’s Club awards, closing $1B+ in sales, and operating across 48 countries. But the moments that shaped him weren’t the accolades—they were the setbacks.

He started in Boston, broke and boiling noodles in a cramped apartment, grinding through a commission-only role. Then came the $1M deal he lost in Sydney—a deal he thought he’d won, until IBM swooped in with a 40-person team and outplayed him at every level. That moment didn’t break him. It became a turning point.

Stephen adopted MEDDIC, built his process from the ground up, and never looked back. Whether selling for IBM, startups, or scaling teams across continents, his career has been built on three things: grit, authenticity, and a relentless commitment to doing the work. He doesn’t chase trends—he trusts the process.

This is the real story of sustained excellence in sales. No hacks. No fluff. Just lessons earned the hard way.

Let’s get into it.

The Making of a Sales Champion

What does it take to become a perennial top performer in sales? For most, making President’s Club even once is a career highlight. For Stephen Cottrell, it’s a way of life—he’s achieved this elite status 29 times in 35 years, selling over a billion dollars in transactions across 48 countries. In this episode Pree sat down with Stephen to uncover the habits, mindset, and pivotal moments that have shaped his extraordinary career.

This post distills the wisdom from their conversation, offering actionable insights for anyone looking to elevate their sales game or lead high-performing teams.

Early Lessons: Grit, Resilience, and the Power of Sport

Stephen’s journey began not in a boardroom, but on the tennis courts of his hometown. Inducted into his high school’s Hall of Fame, he credits his athletic background for instilling the grit and resilience that would later define his sales career. “When you’re on the tennis court, you’re by yourself. There’s no one to help you. You have to work your way out of tough situations,” Stephen recalls.

The lessons from sport—handling pressure, embracing competition, and learning from losses—translated seamlessly into the world of sales. Growing up as the youngest of several brothers, Stephen developed toughness and a competitive edge, constantly striving to keep up. These early experiences built the foundation for his future success.

The Boston Years: Noodles, Rats, and the Value of Hard Work

Every sales legend has humble beginnings. For Stephen, that meant a cramped apartment in Boston’s North End, living on noodles and spaghetti, and sharing his kitchen with the occasional rat. “I was paying $20,000 in rent on a $22,000 salary,” he laughs. The struggle was real, but it taught him the value of hard work and resourcefulness.

His first real break came when a manager recognised his potential and gave him a shot in sales. “Money made the decision for me, I had none,” Stephen admits. But it was the hunger to succeed, both literally and figuratively, that propelled him forward.

Pivotal Moments: Learning from Failure and the Birth of a Methodology

No career is without setbacks. Stephen’s “aha moment” came after losing a seven-figure deal in Sydney. Despite being told he was the chosen vendor, the deal slipped away to a competitor who had outmanoeuvred him at multiple levels. “I was single-threaded, only had one contact. They completely outflanked me,” he reflects.

Rather than chalk it up to bad luck, Stephen sought a better way. This led him to embrace the MEDIC sales methodology. A structured approach that dramatically increased his win rate. “Instead of winning 10% of deals, you can win 60-70%,” he says. The key was to find the gaps, follow a process, and never rely on randomness.

The MEDIC Framework: A Blueprint for Sales Excellence

For those unfamiliar, MEDIC stands for:

• Metrics: Quantifiable value you can deliver (time or cost savings)
• Economic Buyer: The person with the power to sign the deal
• Decision Criteria: How the customer will evaluate solutions
• Decision Process: The steps the customer will take to make a decision
• Identify Pain: The core problem your solution addresses
• Champion: An internal advocate who sells on your behalf

Stephen emphasises that having a process is non-negotiable. “You won’t close every deal, but you’ll know where you stand and what’s missing,” he explains. Over the years, he’s seen variations like MEDDIC and MEDDPICC, but the core principles remain the same.

Habits of High Performers: Consistency, Authenticity, and Relentless Work Ethic

What separates the good from the great? For Stephen, it comes down to a few non-negotiable habits:

• Consistency: “Whatever your process is, stick to it. Consistency is everything.”
• Authenticity: “Be genuine. People can tell when you’re real. I’m not afraid to admit when I’m having a bad day.”
• Embracing Discomfort: “Get comfortable being uncomfortable. The industry changes fast, you have to adapt and reinvent yourself constantly.”
• Work Rate: “If I don’t win, I’m okay with it as long as I haven’t been outworked. My work rate is 70-80 hours a week. I try to outwork everyone.”

Stephen also stresses the importance of being a trusted advisor, not just a vendor. “I try to make every deal a win-win. I want to be a partner, not just someone selling a product.”

Navigating Change: Adaptability Across Countries, Roles, and Companies

Stephen’s career has spanned continents, industries, and roles. From startups to global giants like IBM. Each transition brought new challenges, but the underlying principles remained the same. Early on, fear of failure was a motivator; later, it became the thrill of helping customers achieve their goals.

“Whether I was an individual contributor or a leader, in a startup or a large company, I always focused on being a good partner and maintaining a high work rate,” he says. The ability to adapt, stay curious, and keep learning has been crucial to his sustained success.

Conclusion: Earned Success and the Shelf of Champions

As the conversation wraps up, Pree Sarkar points to the shelf behind Stephen, filled with awards that can’t be bought, only earned. Stephen’s story is a testament to the power of resilience, process, and authenticity in sales. His advice is clear: “You can’t control everything, but you can control your effort, your attitude, and your willingness to learn.”

For anyone aspiring to reach the top in sales—or any field—the lessons from Stephen Cottrell’s journey are invaluable. Consistency, a strong process, and a relentless work ethic are the true hallmarks of high performance.