I Used To Be Crap At Sales – Details, episodes & analysis

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I Used To Be Crap At Sales

MySalesCoach.com

Business

Frequency: 1 episode/30d. Total Eps: 29

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.

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🇬🇧 Great Britain - management
18/08/2026
#59
🇬🇧 Great Britain - management
14/08/2026
#73
🇬🇧 Great Britain - management
05/08/2026
#49
🇬🇧 Great Britain - management
04/08/2026
#42
🇬🇧 Great Britain - management
02/08/2026
#78
🇬🇧 Great Britain - management
01/08/2026
#47
🇬🇧 Great Britain - management
30/07/2026
#54
🇬🇧 Great Britain - management
26/07/2026
#43
🇬🇧 Great Britain - management
25/07/2026
#32
🇬🇧 Great Britain - management
20/07/2026
#44

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https://www.linkedin.com/in/markackers/
13 shares
https://www.linkedin.com/company/mysalescoach-com
7 shares
https://www.linkedin.com/in/josh-braun/
1 share

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Score global : 68%

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Cold Calling and Mindset Shifts | EP09 | Jack Frimston

Episode 9

Thursday, August 29, 2024 • Duration 01:14:27

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.

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From SDR Struggles to Top Sales Leader at Gong | EP08 | Sarah Brazier

Episode 8

Wednesday, August 14, 2024 • Duration 01:05:09

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

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Ex Global Sales Leader at Rolls Royce and Motorola Talks Sales Psychology | EP07 | Steve Myers

Episode 7

Wednesday, July 24, 2024 • Duration 01:30:55

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 understanding your scripting from childhood in order to overcome it as a salesperson
The need for emotional intelligence as a leader, how to really motivate your team (no dangling the carrot here)
Strategies for maintaining focus and productivity within your team.
The burning question - can anybody and everybody be coached?

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.

The Power of Sales Coaching and Self Development | EP06 | Jack Hankey

Episode 6

Wednesday, July 10, 2024 • Duration 01:05:03

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

From Sales Struggles to Sales Leader at Klaviyo | EP05 | Kaitlen Kelly

Episode 5

Wednesday, June 26, 2024 • Duration 01:03:13

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

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Top Social Seller Shares Her Story to Success In Sales | EP04 | Holly Allen

Episode 4

Tuesday, June 11, 2024 • Duration 01:01:01

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

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Benjamin Dennehy's Most Honest Interview YET| EP03 | Benjamin Dennehy

Episode 3

Wednesday, May 29, 2024 • Duration 01:13:50

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

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From Telesales To Sales Leader at Allego | EP02 | Stuart Taylor

Episode 2

Wednesday, May 22, 2024 • Duration 56:52

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 sales35:47 Improving his sales skills through coaching38:36 Realising his potential for growth after years of repetition 44:02 How he rates his sales skills now, and areas for improvement51:09 The opportunities Sales provides59:41 Impact of coaching on sales team performance11:15 Advice for those struggling and importance of taking action

Social Selling Superstar Shares His Story To Success | EP01 | Tom Boston

Episode 1

Tuesday, May 21, 2024 • Duration 50:26

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

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I Used To Be Crap At Sales - Trailer

Wednesday, March 6, 2024 • Duration 01:22

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.

Read moreCollapse