Podcast Episode 3 - Benjamin Dennehy

Posted by Bec Turton

From Struggling Salesman to Sales Trainer Extraodinaire: The Benjamin Dennehy Story

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

When you think Sales Training, it's hard not to think Benjamin Dennehy.

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 a brutally honest discussion, pulls no punches, and offers a huge amount of wisdom for any aspiring sales professional.

He 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.

Another insight Ben shares is the power of persistence and self-belief.

At one point he was £45,000 in debt and on the brink of giving up.

However, his determination to master sales and the support from his mentors helped him turn his career around. His story is a key reminder that success often requires pushing through the hardest times.

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Highlights from the episode:

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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