I Used To Be Crap At Sales

Most people get their first sales management role because they were good at selling and good at putting themselves forward. Nobody warns them it's a different job - or that the drive that got them there can be the same thing that burns them out. Callum Mackay moved into management early in his career, building and leading sales teams through startup and scale-up environments. He's honest about the...

Episode 27: Why the Best Salespeople Struggle Most When They Become Managers Most sales managers are promoted because they were great at selling. The problem is that selling and managing are two different jobs - and nobody tells you that before you take the role. 📥 Download the Modern Revenue Leader's Sales Coaching Manual: https://bit.ly/4nyx5m2 🔗 Connect with Mark Ackers on LinkedIn 🔗 Connect...

Why do top performers consistently close more deals — even when they’re selling the same product, to the same market, with the same tools? In this episode, Scott Cowley breaks down the “3 Whys” Framework — the system elite sellers master that most reps never even think about. Top performers don’t win because they have better personalities, smoother pitches, or clever hacks. They win because they d...

Most salespeople don’t fail because they can’t sell — they fail because of mindset. In this episode, Jessica A. Williams, Founder of Just Williams, joins Mark Ackers to expose the two silent killers that quietly destroy sales careers: need for approval and impostor syndrome. From being kicked out of school to leading an award-winning B Corp, Jessica shares the raw truth about people-pleasing, burn...

Most salespeople stay stuck in the middle of the pack. Some even survive decades in sales without ever breaking through. But a small group — just 15% — consistently smash target, year after year. In this episode, our host Mark Ackers sits with sales influencer and coach Niraj Kapur shares how he went from “horrendous at sales” (his words) to becoming one of the most respected trainers in the indus...

What happens when a seasoned sales leader enters one of the most intense BBC reality shows on TV? Andrew Jenkins spent over 20 years in Sales — building trust, leading teams, and coaching people through high-pressure sales at Lloyds Bank. Then he brought those same skills — listening, emotional intelligence, and calm under pressure — into the castle on The Traitors. The result? He made it to the F...

If you’ve ever felt the tension between sales and marketing… you’re not alone. In this episode, Mark Walker (who's lived both lives) joins our host Mark Ackers to explore one of the most persistent pain points in B2B: sales and marketing alignment. From junk MQLs to misattributed pipeline, they pull no punches in exposing the outdated structures, broken metrics, and political infighting that derai...

🎤 In this must-listen episode of The "I Used to Be Crap at Sales" Podcast, host Mark Ackers interviews Will Aitken, one of the most recognised voices in sales content today.  Will is a former SaaS AE turned sales coach, keynote speaker, and viral content creator with over 140,000 LinkedIn followers and millions of views across TikTok and YouTube. He’s built a global audience by combining relatabl...

Leading a global SDR team? Just promoted to SDR manager? This episode is packed with real-world advice from Catherine Olivier, VP of Global Sales Development at Cognism, on how to build and lead high-performing sales development teams—without burning out or losing your team’s trust. Catherine shares hard-earned lessons from her experience leading SDR teams across the US, UK, Germany, and France. S...

In this unmissable episode of The I Used To Be Crap At Sales Podcast, legendary sales trainer Josh Braun , joins our host Mark Ackers for a deep, unfiltered dive into what really drives consistent sales performance. If you’re a sales rep chasing targets, a team leader trying to motivate your reps, or a founder building a sales motion—this episode is your blueprint for rewiring your sales mindset ....

How do you truly motivate a sales team? Most sales leaders struggle to keep their teams engaged and performing at their best - especially with 53% of the workforce being made up of Millennials and Gen Z. In this episode, our host Mark Ackers sits down with Phil Putnam , the author of Desire-Based Leadership, to uncover the secrets behind scaling high-performing sales teams and retaining top talent...

Building & Scaling Successful Sales Teams Sales leaders and ambitious reps, this one’s for you! In this episode of I Used to Be Crap at Sales , Mark Ackers sits down with Richard Bounds, a seasoned sales leader and fractional CRO, to unpack the biggest challenges in scaling sales teams, hiring top talent, and driving sustainable sales growth. Richard shares hard-earned lessons from over 35 yea...

In this episode of The "I Used To Be Crap At Sales" Podcast, hosted by Mark Ackers, we dive deep into the art of sales development. Our guest, Gabe Lullo, is co-founder and CEO of Alleyoop. the global leader in prospecting and outsourced sales development. Thousands of companies try to replicate what Alleyoop does, but Gabe reveals the secrets behind their unparalleled success. From delivering hig...

Stepping into your first sales leadership role, or aspiring to walk the beaten path from successful sales rep to leader? It’s a whole new ballgame, and not all top-performing sales reps are cut out for the challenge. In this episode of I Used to Be Crap at Sales , Mark Ackers sits down with seasoned sales veteran Alan Clark to unpack the truths every first-time sales leader needs to hear.  Drawing...

In this episode of the "I Used to Be Crap at Sales" podcast, Dougie Loan shares his inspiring journey from a young call center rep to CRO of thriving SaaS company SourceWhale. If you’re passionate about SaaS sales career growth, overcoming sales challenges, and developing leadership traits, this is a must-watch! We delve into critical topics like sales coaching, building credibility, transitioning...

Ep. 13 - I Used To Be Crap At Sales | James Ski Building Your "Sales Confidence" In This episode of the "I Used To Be Crap At Sales" Podcast, our host Mark Ackers sits with one of LinkedIn’s top global sellers who knows exactly how to shatter sales obstacles and fuel unstoppable confidence from doing it himself first hand - James Ski. After all, who could possibly be more expert in building confid...

Mastering Sales Leadership: Proven Strategies to Crush Limiting Beliefs and Skyrocket Sales Performance” In This episode of the "I Used To Be Crap At Sales" Podcast, our host Mark Ackers sits with Bryan Mulry, ex salesperson at Google and Salesloft. This episode will give you valuable insights into what the best sales leaders at huge companies do to get the best out of their reps. Bryan, now an ex...

From Scrapping Her Way Into Sales, to Scaling With Datamaran: Carly's Unconventional Path To Leadership, and Her Secrets For Building High-Performing, Winning Teams”   In this episode, our host Mark Ackers dives deep into Carly’s story, which is packed with lessons for any sales leader. Carly candidly reveals how she “scrapped her way” into the sales team, facing tough wake-up calls, and overcomin...

From Sales Struggles to Sales Leadership Mastery:  Chris Dawson on Coaching SDRs, Escaping the Leadership Hamster Wheel and Leading Teams to Win! In this episode of the I Used To Be Crap At Sales Podcast, Chris Dawson sits with our host Mark Ackers to take sales leaders on an insightful journey through his personal experiences and lessons learned from over 25 years in the sales arena. Chris has he...

Debt Collection, Demotions And Finding Meaning In Life Through Death. The captivating story of how Jack Frimston transformed from Del Boy dreaming of playing the O2 arena to top performer in Sales. In this episode of I Used To Be Crap At Sales, Jack Frimston sits with Mark Ackers, leading us through his unconventional journey from boy band dreams to becoming a top performer and sales leader. Sales...

From Center Stage, Scripts and SDR Struggles, to Successful Sales Leadership at Gong. The captivating story of how Sarah Brazier’s acting roots helped her to weather the storms of sales - rising from a self proclaimed ‘F Player’, to an A player who pioneered a new era with Gong. In this episode, Sarah shares her unique journey into Sales - and how her background in Theater gave her a distinctive e...

Swapping Encyclopedias For Rolls Royces: The Transformation of Steve MyersFrom being admittedly ‘crap at sales’ and fired for nonperformance, to eventually becoming a global sales leader, working at the likes of Rolls Royce, Motorola and Sandler, Steve's story is filled with valuable lessons and insights for sales leaders. Alongside our host Mark Ackers, Steve discusses: The importance of understa...

From Tennis Prodigy, to Amazon Driver, to Successful Sales Leader: The Inspiring Transformation of Jack Hankey Get ready for an inspiring tale of tennis, testing times, and transformation! In this captivating episode of "The I Used to be Crap at Sales Podcast," our host Mark Ackers sits down with Jack Hankey, Head Of Sales Development at Leyton, to uncover his remarkable journey from struggling sa...

In this episode, Kaitlen Kelly shares her gritty, behind-the-scenes journey from fashion racks to sales, transforming her initial struggles into monumental triumphs. Packed with raw honesty, this conversation is a treasure trove of practical advice and inspiring anecdotes, making it a must-listen for anyone looking to excel in sales. Episode Highlights: 00:00 - Introduction and background on Kaitl...

In this episode, Mark Ackers chats with Holly Allen, an account executive at Deel. Holly shares her journey from a party-loving university student to a successful sales professional, sharing insights on persistence, self-belief, and continuous learning. An open and honest conversation about the highs and lows of a career in sales. Episode Highlights: 00:00 - Introduction 01:44 - Holly's early care...