Services -- -- Blog -- -- Podcast-- -- About

Services ---- Blog ---- Podcast---- About

Practical Strategies for Entrepreneurs and Salespeople from The UK's Most Hated Sales Trainer Benjamin Dennehy

2244 - Practical Strategies for Entrepreneurs and Salespeople from The UK's Most Hated Sales Trainer Benjamin Dennehy

July 28, 20253 min read

The Unvarnished Truth About Sales: Lessons from the UK’s Most Hated Sales Trainer, Benjamin Dennehy

Custom HTML/CSS/JAVASCRIPT

In the world of sales, few voices are as candid—or as controversial—as Benjamin Dennehy, widely known as the UK’s most hated sales trainer. In this episode, hosted by Josh Elledge, Benjamin pulls no punches as he exposes the uncomfortable realities of sales, debunks persistent myths, and offers actionable strategies for founders, salespeople, and small business owners. This blog post distills the key themes and expert advice from their conversation, providing a comprehensive guide for anyone looking to elevate their sales game.

The Realities of Sales and Building Repeatable Success

Benjamin starts by addressing an uncomfortable truth: most people in sales didn’t choose the profession—they stumbled into it. This lack of passion often leads to mediocrity, with many salespeople operating at a “seven out of ten” level, performing just enough to get by. To break through this, Benjamin advocates for treating sales as a craft that demands continuous improvement and investment in proper training. He emphasizes the importance of building a repeatable sales process, focusing on long-term relationships rather than just closing deals.

Benjamin also talks about the “founder-led sales trap” where entrepreneurs, passionate about their products, often dread the sales process. Founders frequently hesitate to delegate or hire the right salespeople, leading to burnout and stagnation. He encourages founders to invest in structured sales training, create a clear sales process, and treat sales with the same importance as product development or finance. This shift in mindset is crucial for scaling a business beyond the founder's efforts.

Finally, Benjamin discusses the common pitfalls businesses face when hiring salespeople. He warns against hiring based on charisma alone and stresses the need to look for candidates who demonstrate solid sales processes and results. Without a clear and documented sales approach, businesses will continue to struggle with underperforming teams. He advises on setting clear metrics and ensuring new hires are onboarded with proper training to drive predictable and repeatable sales success.

About Benjamin Dennehy

Benjamin Dennehy is the Founder of Sales Matrix Courses, a platform offering comprehensive training and coaching for sales professionals. Known for his blunt, no-nonsense approach, Benjamin helps businesses confront uncomfortable truths about sales, break through mediocrity, and achieve repeatable success.

About Sales Matrix Courses

Sales Matrix Courses is a sales training platform created by Benjamin Dennehy. The courses are designed to help professionals and businesses develop stronger sales foundations, overcome common challenges, and create repeatable, predictable sales outcomes.

Links Mentioned in This Episode:

Episode Highlights:

  • Why most salespeople fall into the profession without passion or preparation

  • The “founder-led sales trap” and how to avoid it

  • The importance of treating sales as a craft and investing in ongoing training

  • Why hiring the right salesperson requires more than just charisma

  • How big companies fail at sales training and what small businesses can do differently

Conclusion

Benjamin Dennehy’s direct approach to sales offers a wake-up call for anyone stuck in mediocrity or struggling to scale their business. His message is clear: sales is a craft that demands discipline, self-awareness, and continuous improvement. Whether you’re a founder, an experienced salesperson, or new to the field, the key to success begins with confronting uncomfortable truths and committing to mastering the craft.

Ready to take your sales skills to the next level?
Start by reflecting on your own motivations, invest in real training, and don’t be afraid to seek help from those who’ve walked the path before you.

Apply to be a Guest on The Thoughtful Entrepreneur: https://go.upmyinfluence.com/podcast-guest

More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.
What is your #1 Lead Generation BLOCKER? Take my free quiz here.
Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.

Don’t forget to subscribe to The Thoughtful Entrepreneur and thank you for listening. Tune in next time!

👋 30-year veteran journalist, serial entrepreneur & B2B relationship-builder • 🎙️ Host, The Thoughtful Entrepreneur (2,200+ episodes) • 🚀 Founder, UpMyInfluence (2x 7-figure companies) • 📺 2,500+ media appearances (TV, radio, Forbes, columnist) • 🤝 Fractional CRO & B2B networking strategist (helped 250+ founders land high-value clients—no cold outreach) • 🐕 Dog lover, advocate for real human connection

Josh Elledge

👋 30-year veteran journalist, serial entrepreneur & B2B relationship-builder • 🎙️ Host, The Thoughtful Entrepreneur (2,200+ episodes) • 🚀 Founder, UpMyInfluence (2x 7-figure companies) • 📺 2,500+ media appearances (TV, radio, Forbes, columnist) • 🤝 Fractional CRO & B2B networking strategist (helped 250+ founders land high-value clients—no cold outreach) • 🐕 Dog lover, advocate for real human connection

LinkedIn logo icon
Instagram logo icon
Youtube logo icon
Back to Blog


Sick of B2B 'LeadGen'
That Wastes Time and Doesn’t Work? 😖

We’ve launched 250+ interview podcasts for 6- and 7-figure founders just like you.

Chasing cold leads is broken 🚫 and is considered amateur behavior today. 🤢

Ready to stop wasting time and start meeting the right people every single week?

Click to see the step-by-step system real leaders use.

My full masterclass workshop: Attraction Mastery - The FastPass to Magnetizing High-Value Partners and Clients Week After Week:

Watch my free video class about creating unlimited high-ticket intros:

Watch my free 4-video series - no opt-in required:

My epic blog post about how I run a DSLR camera as a webcam:

Click to see the step-by-step system real leaders use.

Listen & Subscribe to The Thoughtful Entrepreneur

Say: “Hey, Siri / Alexa. Play The Thoughtful Entrepreneur Podcast.”

Join our community of over 120K!

UpMyInfluence © 2025

1969 S Alafaya trail PMB #230 Orlando, FL 32828