7 episodes

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.

I Used To Be Crap At Sales MySalesCoach.com

    • Business

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.

    EP06 - Jack Hankey, Leyton

    EP06 - Jack Hankey, Leyton

    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

    • 1 hr 5 min
    EP05 - Kaitlen Kelly, Klaviyo

    EP05 - Kaitlen Kelly, Klaviyo

    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 career10:11 - Kaitlen rating her early sales skills and an awkward sales moment16:16 - Kaitlen's bold career switch from fashion to sales31:34 - Kaitlen turns into a robot at her first sales event39:29 - Developing the mindset to overcome fear and rejection in sales46:11 - Kaitlen's blueprint to success for new SDRs in their first six months53:10 - How Kaitlen gets organised, plans and time blocks1:00:00 - What Kaitlen would do differently if she could start her career again

    • 1 hr 3 min
    EP04 - Holly Allen

    EP04 - Holly Allen

    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

    • 1 hr 1 min
    EP03 - Benjamin Dennehy

    EP03 - Benjamin Dennehy

    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

    • 1 hr 13 min
    EP02 - Stuart Taylor

    EP02 - Stuart Taylor

    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 Introduction13:23 Early struggles in his sales career at Barclays26:45 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
    For shownotes visit: https://www.mysalescoach.com/blog/podcast-ep02-stuart-taylor

    • 56 min
    EP01 - Tom Boston

    EP01 - Tom Boston

    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 - Introduction01:44 - Tom’s early career and transition to sales04:11 - First sales role and cold calling challenges06:52 - Moving into the SaaS world08:46 - Becoming Brand Awareness Manager at SalesLoft16:54 - Overcoming struggles and finding success in Sales22:21 - Importance of resilience and support systems37:08 - Advice for new sales professionals45:32 - Reflections and final thoughts
    For shownotes visit:  https://www.mysalescoach.com/blog/podcast-ep01-tom-boston

    • 50 min

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