In this replay episode of Coach to Scale, host Matt Bonelli sits down with Ben Johnson, VP at Zendesk, seasoned sales leader, and longtime CrossFit coach, to explore what it really takes to build a thriving sales career. Drawing on more than 25 years of experience at companies like Dell, Oracle, Workday, and Zuora, Ben challenges the myth that sales success is measured only by the quarter. Instead, he shares why the true differentiator is consistent coaching, a culture of accountability, and the willingness to sharpen your sword through personal development.
Listeners will walk away with actionable insights on transforming performance improvement plans into coaching opportunities, creating cultures where vulnerability is strength, and distinguishing between “must-dos” and “how-tos” in sales leadership. From rebranding coaching as a growth engine to embracing “deeds, not words,” this conversation delivers timeless lessons for sales reps, managers, and leaders who want to play the long game and win.
Key Takeaways
1. Coach to the career, not the quota – Long-term success comes from developing people beyond just hitting short-term numbers.
2. Performance Improvement Plans can be growth tools – When used correctly, PIPs should guide reps toward improvement, not serve as a punishment.
3. Coachability is the key to success – The most successful reps are those open to feedback, willing to adapt, and eager to learn.
4. Culture starts at the top – A strong coaching culture must be modeled by leadership and reinforced consistently across the organization.
5. Preparation and debriefing matter as much as the meeting – Success comes from doing the pre-work, running the meeting, and reflecting afterward to continually improve.
6. Focus on “must-dos” vs. “how-tos” – Clear expectations around the basics (like CRM hygiene) free up time to coach on higher-value selling skills.
7. Deeds, not words – Accountability is proven through consistent actions, not promises.
8. Get the bad news early – Addressing risks and challenges upfront allows teams to respond effectively instead of scrambling at the last minute.
9. Invest in personal development – Ongoing learning, mentorship, and self-improvement are essential to staying sharp and thriving in sales.
10. Find mentors and be one – Having someone to guide you (and paying it forward to others) accelerates growth and resilience in a sales career.