EP23 | Andrew Jenkins
The Hard Lessons That Make Great Sales Leaders:
When Andrew Jenkins tells you he’s been through the grinder, believe him. His story isn’t just about sales—it’s about survival, resilience, and transformation.
After surviving a horrific car accident that reshaped his outlook on life, Andrew rebuilt his path—first in corporate sales, where he rose through the ranks as an AE and sales leader, and later on national television as a contestant on popular BBC show "The Traitors".
Today, Andrew describes himself as an authentic and relatable motivational speaker, educator, mentor, and coach. His mission? To inspire people by breaking stigmas around mental health and helping others lead more complete and fulfilled lives.
In this episode of I Used to Be Crap at Sales, Andrew joins our host Mark Ackers to dissect what makes sales hard, what makes leaders great, and how coaching, self-awareness, and vulnerability are the real unlocks - and of course an insight into his journey on The Traitors.
Watch The Episode:
Or listen on Spotify or Apple here.
Our 5 Biggest Takeaways
You can be a top rep and still not understand sales.
Andrew kicks off with an honest reflection on his early years: he was succeeding by the numbers but failing by the fundamentals. He describes how he relied heavily on brute force—booking meetings, following scripts, and closing quick wins—without really understanding buyer pain.
"I didn't really know what I was doing. I could book meetings and close deals, but I wasn't diagnosing problems—I was pitching." - Andrew
Mark chimes in here, noting that this is a common trap for reps:
"You start thinking success equals habits, when really, it's often just timing or territory."
The Fix:
Andrew had to deconstruct his entire sales process. He started listening more, asking better questions, and focusing on uncovering root causes rather than rushing to solutions. His wake-up call? Watching more seasoned reps navigate discovery and realising how much he’d skipped over.
"I thought I was good. But I was just busy." - Andrew
Becoming a Manager Doesn’t Make You a Leader
Management is not mentorship. Telling someone what to do isn't the same as coaching them through how to think.
"I thought managing was about giving answers. But my best moments were when I shut up and let my reps figure it out." - Andrew
Stepping into management, Andrew admits he defaulted to control. If someone struggled, he’d jump in with the fix. But what he learned—often painfully—is that solving their problems didn’t scale and didn’t develop anyone.
Mark reflects on a similar journey:
"There's a moment when you realise being right isn't the win—getting them to think differently is."
The Fix:
Andrew got curious. Instead of diagnosing for his reps, he’d ask, "What do you think is really going on here?" This shift from directive to developmental created more ownership. He also learned that clarity around expectations—what good looks like, how we measure it—was critical.
"Once I stopped trying to be the hero, I became a better coach." - Andrew
Coaching isn’t winging it. It needs structure.
Coaching Without a Playbook?
Andrew confesses that early in his leadership career, coaching was sporadic and informal. He’d check in, give feedback on the fly, and assume it landed. It didn’t.
"If your coaching is just a gut check, it's not coaching—it's a chat." - Andrew
Mark agrees, adding:
"We assume reps are absorbing insights just because we say them. But without a consistent structure, it doesn’t stick."
The Fix:
Andrew began approaching coaching like pipeline reviews—with a framework and purpose. He prepared for each 1:1, tracked rep goals, and aligned coaching to skill development, not just performance metrics. This created continuity and accountability.
"When reps see you're as invested in their growth as you are in the forecast, that’s when trust kicks in." - Andrew
The best reps aren’t always the most confident—they’re the most coachable
As a sales leader, a common challenge you face is dealing with pressure and performance dips across the team.
"I had reps who were struggling, and instead of fixing them, I asked them to reflect. That vulnerability unlocked their growth." - Andrew
Pressure reveals gaps. Andrew recalls a pivotal moment with a rep who hit a slump. Instead of diving into call reviews or metrics, he asked, "What do you think is holding you back?" The rep’s answer? "I don’t think I belong here."
Mark jumps in:
"That’s the stuff you don’t hear in dashboards. Real coaching is emotional, not just tactical."
The Fix:
Andrew leaned into silence. He gave reps space to reflect, articulate their fears, and own their journey. That act of listening—without judgment or rushing to solutions—created psychological safety. Performance rebounded not because of better tactics, but because of renewed belief.
"They didn’t need answers. They needed permission to struggle and work it out." - Andrew
Conclusion: Sales Leadership Is a Skill Of Its Own
Andrew Jenkins’ journey is a masterclass in humility, growth, and the grind of becoming a true leader. He didn’t arrive at coaching because it was easy—he arrived because it was necessary. From AE to mentor, the hard lessons stuck. And that’s what makes his perspective invaluable.
If you’re a leader wondering why your team isn’t leveling up, Andrew’s story is your mirror: coaching is the unlock.
Listen To The Full Podcast Here:
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