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, performance skyrockets.
We dive into real-world leadership mistakes, how to avoid costly attrition, and why traditional motivational tactics no longer work.
You’ll hear powerful insights on:
You'll learn:
If you’re serious about scaling your sales team, retaining your top talent, and mastering modern sales leadership, this episode is a must-listen.
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 sales leaders can make a real impact. Discover the biggest hiring mistakes sales leaders make, how to spot bad hires fast, and why company culture beats experience when building a team.
We also dive into the evolution of sales leadership, from old-school “work harder” mentalities to today’s data-driven, AI-powered coaching approaches. If you’re an aspiring sales leader, Richard’s insights on avoiding first-time leadership mistakes and building a high-performing team will be game-changing.
Tune in to learn:
• How to scale a sales team without ruining company culture
• How fractional sales leaders accelerate growth as quickly as possible, and how Richard measures success
• The biggest mistake sales leaders make when hiring
• How modern sales coaching transforms performance
• How AI and data are reshaping the sales landscape
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 and processes.
Whether you’re looking to support your team in setting up more demos, booking high-value meetings, or refining outreach strategy, this episode is a must-listen. Learn how to target the right prospects with the right messaging and ensure every single call and email hits the mark.
Don’t miss this conversation packed with sales tips, prospecting strategies, and leadership advice from an expert whose company helps scale some of the world’s most successful sales development teams. If you’re in SaaS, tech, or sales leadership, this episode will transform how you approach your pipeline.
Find out about our £20 memberships here:
https://www.mysalescoach.com/membership-pricing
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 building a team of “mini-me’s” is a recipe for disaster.
Learn from Alan’s wins, like leading a SaaS company to a 10x ARR exit, and his missteps along the way, such as assuming success without consistent alignment with leadership. His personal anecdotes and practical advice provide a roadmap to navigate the often rocky path to becoming an effective sales manager.
You’ll discover why empathy in leadership is essential (but doesn’t mean being soft), how to avoid hiring biases, and the importance of digging deeper in one-on-one conversations. Alan also reveals the traits that separate top individual contributors from successful sales managers, and why failing to build trust and credibility with your team can derail your career.
If you’re an aspiring sales manager, new to leadership, or looking to develop your sales coaching skills, this episode offers actionable advice to set you up for success. Learn how to navigate the pitfalls, lead with confidence, and turn failures into opportunities for growth. Don’t miss out—your leadership journey starts here!
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 leadership skills.
🔑 What You’ll Learn in This Episode:
• The mindset and traits essential for success in SaaS sales and leadership.
• Strategies for overcoming sales pressure and improving the sales process.
• How to transition from sales to customer success and thrive in both roles.
• The importance of emotional connection and resilience in sales.
• Real-life sales horror stories and how to turn mistakes into learning opportunities.
🎯 Who Should Watch:
• Aspiring and experienced SaaS sales professionals.
• Sales leaders seeking actionable coaching techniques.
• Anyone looking to fast-track their sales career growth.
✅ Find out more about MySalesCoach
/ https://www.mysalescoach.com/
✅ Connect with Us:
Follow Mark Ackers on LinkedIn: / https://www.linkedin.com/in/markackers/
Follow MySalesCoach on LinkedIn: / https://www.linkedin.com/company/mysalescoach-com
Follow Dougie Loan on LinkedIn: / https://www.linkedin.com/in/dougieloan/
✅ SUBSCRIBE to the audio Podcast I USED TO BE CRAP AT SALES:
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#SaaSSalesCareerGrowth #SalesCoaching #SalesLeadership #CustomerSuccess #SalesProcess #SalesMotivation #CareerProgression #SalesChallenges
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 actionable strategies for overcoming common sales mistakes, breaking free from their own limiting beliefs, and how to level up their performance.
Bryan emphasises the importance of understanding the customer’s pain points and the power of continuous self-improvement. He recounts key moments from his career, including the value of cold calling, dealing with rejection, and how sales leadership can drive team success through empowerment and tailored coaching. Bryan also offers insights into maintaining motivation in a high-pressure sales environment and navigating challenges like sales burnout.
The questions we answer in this episode:
How can I overcome limiting beliefs in my sales career?
• Bryan Mulry shares how to identify and break free from the limiting beliefs that hold many salespeople back.
What are the winning habits of top-performing salespeople?
• The episode explores the traits and practices that set the best sellers apart from the rest, based on Bryan’s extensive experience at Google and SalesLoft.
How do I deal with rejection and improve my cold calling success?
• Bryan discusses how he handled early sales mistakes, like hanging up on prospects during cold calls, and what strategies helped him succeed over time.
What does effective sales leadership look like?
• Listeners will learn about the traits and habits of strong sales leaders, including how they empower their teams and foster a culture of growth and development.
How can I avoid burnout in high-pressure sales environments?
• Bryan provides insights into recognizing early signs of burnout and how salespeople can maintain balance and motivation.
How can I use sales coaching to improve my performance?
• Bryan talks about how coaching helped him break through challenges and why ongoing coaching is crucial for professional growth in sales.
Listeners will come away with practical techniques to improve their sales habits, foster stronger client relationships, and create a coaching environment that develops their team’s skills. If you’re looking to gain insight into what sets top performers apart in the sales world, this episode is packed with valuable lessons.
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 success in fast-growing companies.
Carly also discusses the challenges and joys of inheriting a sales team, her approach to personalised coaching, and the importance of understanding team motivations. She emphasises the significance of transparency and building genuine relationships within a sales team to foster growth and accountability.
Carly’s practical tips on spotting burnout, maintaining empathy as a leader, and dealing with the challenges of scaling a startup will resonate with sales leaders managing global teams or navigating high-speed environments.
This episode is a must-listen for sales leaders looking to scale their own teams and sharpen their leadership skills, this episode is filled with actionable insights on sales coaching, leadership, and strategy in a fast-paced world.
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 from someone who admits he “used to be crap at sales” into a highly successful sales leader and coach.
Now a director at ‘6th Door’, Chris designs and delivers tailored sales training and coaching programmes to businesses worldwide. In this episode, he shares invaluable, powerful advice on spotting burnout in your reps, simplifying SDR coaching, and how to help your reps overcome the monotony of sales. He also tackles the biggest mistake sales managers make and reveals how to break free from the leadership hamster wheel by putting your team first.
This episode is a must-listen for anyone serious about elevating their sales leadership game and getting the best from their team.
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.
Jack shares his candid experiences with early career mistakes, from misguided sales tactics to rapid promotions and demotions, and how these tough lessons ultimately shaped his mindset and approach to sales.
You can look forward to gaining insights into building resilience, fostering a growth mindset, and leading with authenticity while helping your team navigate the challenges of 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 edge and an advantage in key sales skills like storytelling, communication, and empathy.
These skills propelled her from a struggling SDR and self proclaimed 'F player' who ‘struggled with everything’ and was made to feel like she wasn't worth the time to coach by her manager, to becoming a top performer at Gong and eventually co-founding Dimmo.
Sarah discusses the importance of coaching, building a personal brand on LinkedIn, and how to navigate the challenges of modern day sales.
With plenty of actionable strategies for coaching, team building, and staying ahead in the ever evolving sales landscape - whether you're a seasoned sales leader or just starting out, this episode is a must-listen.
Highlights from the episode:
00:00 - 02:56 Introduction to Sarah Brazier: From Acting to Sales Leadership
02:56 - 07:31 The Power of Storytelling in Sales
07:31 - 15:56 Translating Acting Skills into Sales Success
15:56 - 24:30 Embracing Failure: The Nine-Month Struggle
24:30 - 32:59 Overcoming Early SDR Career Challenges
32:59 - 36:47 Joining Gong: A Last-Chance Opportunity
36:47 - 42:28 The Gong Experience: Building Confidence and Community
42:28 - 46:58 The Impact of an Excellent Leader
46:58 - 53:09 Leveraging LinkedIn: Building a Personal Brand
53:09 - 57:29 Advice for Sales Leaders
57:29 - 59:44 Sarah’s Ongoing Challenges in Sales
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:
And much more.
Whether you're a seasoned sales leader or just starting out, this episode is a must-listen.
Highlights from the episode:
00:00 - 03:00: From fired to fired up. Steve’s early sales struggles and the pivotal moment that led to his transformation - from fired for non-performance, to Sales Leadership and coaching around 2,000 sales professionals
03:00 - 10:00: The importance of learning and developing sales skills, just like in any other profession.
10:00 - 20:00: The Power of Childhood Scripting. How early life experiences and programming influence adult behavior in sales - understanding childhood scripting to unlock your sales potential
20:00 - 30:00: Overcoming the need for approval, understanding the impact on sales performance - and how to overcome it. “Sales is no place to get your emotional needs met.”
30:00 - 40:00: Finding the right mentor - The role of mentorship in sales success and the value of a good coach in shaping your career.
40:00 - 50:00: The secret to sequencing success - Why getting the sequencing right in sales is crucial.
50:00 - 1:00:00: Looking in the "ugly mirror" - the importance of self-awareness and honesty in sales leadership. Why do sales leaders often opt for more tools rather than developing their team?
1:00:00 - 1:10:00: Steve’s biggest mistakes as a sales leader and what he learned from them.
1:10:00 - 1:20:00: Can anyone be coached? The difference between willingness to be coached and finding the right coach.
1:20:00 - 1:30:54: Common tactical mistakes in sales and how to avoid them.
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 sales, Jack's path was anything but straightforward. But it was his willingness to confront his own shortcomings, overcome his own 'sales ego' and seek out the guidance of a transformative mentor that truly set him on the path to success.
Through Jack's candid and insightful reflections, you can expect invaluable, actionable advice on how Jack overcame being "crap at sales", along with his own impostor syndrome - something he still struggles with today but channels into positive actions.
Jack explains how he harnesses the power of coaching in his role at Leyton, and how he cultivated a struggling team into thriving sales culture with his people first mindset, love of coaching and commitment developing his people.
Whether you're a seasoned sales professional or just starting out, this episode is a must-listen.
Highlights from the episode:
00:00 - Jack's journey from Tennis Prodigy to Sales Superstar
07:00 - The Humbling Realisation: Admitting He Was Actually "Crap" at Sales
17:00 - The Transformative Power of a Coach: How Paddy Turned Jack's Career Around
24:00 - Building a Powerhouse of a Sales team: Jack's Innovative Coaching Approach at Leyton
52:00 - Words Of Wisdom: Overcoming His Own Mindset And Making Imposter Syndrome A Positive
59:00 - Shattering Stereotypes - Redefinining The Perception Of Sales, And What Jack Would Do Differently In His Sales Journey
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
39:29 - Developing the mindset to overcome fear and rejection in sales
46:11 - Kaitlen's blueprint to success for new SDRs in their first six months
53:10 - How Kaitlen gets organised, plans and time blocks
1:00:00 - What Kaitlen would do differently if she could start her career again
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 - The importance of resilience and support systems
33:42 - Key techniques for effective sales communication
45:32 - Advice for struggling sales professionals
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 cases, very uncomfortable questions to prospects - something he says is crucial for uncovering real needs and closing deals effectively.
Episode Highlights:
00:00 - Introduction
01:44 - Ben’s early career struggles and first sales role
06:52 - Learning to sell and the turning point in his career
16:54 - Overcoming financial struggles and persistence in sales
22:21 - The importance of resilience and self-belief
33:42 - Key techniques for effective sales communication
45:32 - Advice for struggling sales professionals
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 sales roles at Sunderland Football Club and a car dealership, bringing his high-volume call center approach to different industries. While he achieved some success, he felt he was repeating the same mistakes for many years without truly improving.
It wasn't until Stuart joined Refract, a SaaS startup, that things changed.
Surrounded by passionate sales leaders, he had an epiphany about how much he had to learn. For the first time, Stu immersed himself in coaching, listening to calls, and continuously developing his skills. He saw massive improvements in just two years.
Now a respected Sales Director at Allego, Stu coaches and mentors teams to achieve their potential. One seller went from £10k to £60k commissions through Stuart's guidance. He takes pride in helping others avoid the struggles of his early career and is a huge advocate for the power of coaching.
He firmly believes that sales can be a hugely rewarding career when done the right way.
Ready to get inspired? You're going to love this episode!
Highlights From The Episode
00:00 Introduction
13:23 Early struggles in his sales career at Barclays
26:45 Difficult mental health period and considering leaving sales
35:47 Improving his sales skills through coaching
38:36 Realising his potential for growth after years of repetition
44:02 How he rates his sales skills now, and areas for improvement
51:09 The opportunities Sales provides
59:41 Impact of coaching on sales team performance
11:15 Advice for those struggling and importance of taking action
For shownotes visit: https://www.mysalescoach.com/blog/podcast-ep02-stuart-taylor
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 the SaaS world
08:46 - Becoming Brand Awareness Manager at SalesLoft
16:54 - Overcoming struggles and finding success in Sales
22:21 - Importance of resilience and support systems
37:08 - Advice for new sales professionals
45:32 - Reflections and final thoughts
For shownotes visit: https://www.mysalescoach.com/blog/podcast-ep01-tom-boston
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.
