I Used To Be Crap At Sales

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, burnout, and rebuilding confidence with boundaries, coaching, and self-awareness.

🔥 You’ll learn:
 • Why need for approval in sales kills performance
 • How impostor syndrome thrives even in top performers
 • The role of self-awa...

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 industry. His story is brutally honest — from reading rejection scripts with no clue what to say, to being nominated for Salesman of the Year.

You’ll d...

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 Final Four.

In this conversation, Andrew unpacks how:
 • Relationship-building helped him avoid votes while others got banished
 • Sales coaching taught him to listen more, speak less — even in a roun...

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From junk MQLs to misattributed pipeline, they pull no punches in exposing the outdated structures, broken metrics, and political infighting that derail revenue teams. You’ll learn how to rethink SDR reporting lines, why most account based marketing (ABM) campaigns fall flat, and what it really means to align around revenue.

🔑 In t...

🎤 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 relatable sales insights with unforgettable humour—and today, he’s opening up like never before.

🔥 What You'll Learn:
👉 Why “need for approval in sales” is the #1 mindset trap holding reps back

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. She unpacks what most first-time SDR managers get wrong, how to avoid managing like your old boss, and the biggest mistakes leaders make in a hybrid, high-pressure sales environment.

Learn how to:
✅...

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.

Josh breaks down why most sellers fail—not from lack of skill, but from clinging too tightly to outcomes and things they can't control. Learn how to det...

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. Phil shares a game-changing leadership framework that shifts the focus from company goals to what employees truly want - because when salespeople believe their job helps them achieve their life goals...

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 years experience in sales, leading and coaching sales teams at companies such as IBM, OpenText, and Software AG. Learn why fractional sales leadership is gaining traction in the startup world and how sa...

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 high-quality leads, accurate data, and scheduled meetings to helping SaaS and tech businesses scale their SDR teams effectively, Gabe shares actionable insights you can use today to supercharge your own sales team...

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 on 20+ years of experience managing diverse teams at global tech giants like SAP and Sage, Alan shares candid lessons learned from his early mistakes—like why build...

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 from sales to customer success, and handling the pressures of recruitment and sales targets. Whether you’re an SDR, AE, or aspiring sales leader, you’ll discover actionable insights to elevate your sales career and le...

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 confidence in sales, than the founder of Sales Confidence itself?

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 expert sales coach at MySalesCoach, shares his journey from being “crap” at sales to mastering his craft at Google, SalesLoft, and beyond. Salespeople and sales leaders will learn...

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 overcoming early mistakes—like almost shutting down her company due to a lead mix-up. Her experience in rising through the ranks, from SDR to Enterprise Sales Director at Datamaran, provides listeners with a roadmap to...

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 held nearly every sales role; from door-to-door, SDR and enterprise level sales, right through to national sales management and training for top 100 companies - and transformed f...

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 leaders will learn valuable lessons about embracing failure, mastering the art of cold calling, and the importance of persistence in a challenging industry.<...

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 edge and an advantage in key sales skills like storytelling, communication, and empathy. 

These skills propelled her from a struggling SDR and self proclai...

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:

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 salesperson to a sales powerhouse through the power of coaching and self development.

From his early days as a tennis prodigy to his unexpected foray into the world of...

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 Kaitlen Kelly's career
10:11 - Kaitlen rating her early sales skills and an awkward sales moment
16:16 - Kaitlen's bold career switch from fashion to sales
31:34 - Kaitlen turns into a robot at her first sales event<...

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 career and transition from university to sales

06:52 - Navigating her first SDR role and learning the ropes

16:54 - Overcoming financial struggles and persistence in sales

22:21...

Welcome to the latest episode of "I Used to be Crap at Sales"! In this episode, Mark Ackers chats with Benjamin Dennehy, the self-proclaimed UK’s most hated sales trainer.

Known for his controversial and no-nonsense approach, Benjamin shares his journey from struggling salesperson to one of the most recognised sales trainers in the UK. Ben delivers an insightful and brutally honest discussion that should leave you inspired and energised.

Ben pulls no punches and shares stories of his early struggles working in sales and how he learned to ask tough, and in some ca...

Welcome to the second episode of "I Used to be Crap at Sales"!

Join MySalesCoach Co-Founder and Head of Sales, Mark Ackers, as he chats with Stuart Taylor, Sales Director at Allego.

Stu began his career in sales over 15 years ago at Barclays Bank. As a young man fresh out of school, he fell into a role in outbound telesales without really understanding what a professional sales career entailed. He struggled immensely in the early days, admitting he was "ignorant and crappy" and contemplated leaving the industry altogether.

Stuart went on to hold...

Mark Ackers sits down with Tom Boston - comedy sales content creator, social selling trainer, keynote speaker, and LinkedIn Top Voice.

Tom shares how he overcame the struggles of cold calling, dealing with rejection, and transforming his sales career through perseverance and a positive attitude. The episode is full of insights, laughs, and practical advice for anyone trying to navigate the world of Sales.

Highlights from the episode:

00:00 - Introduction
01:44 - Tom’s early career and transition to sales
04:11 - First sales role and cold calling challenges
06:52 - Moving into th...

Even the most prominent voices in Sales were crap at Sales once.

Join bestselling Author, Founder and Sales Coach Mark Ackers as he speaks with successful Sales professionals about their early Sales struggles, and how they overcame these challenges to become the people they are today.