The CEO and the Salesman Podcast

Why Most Sales Transformations Fail (And 3 Fixes That Actually Work) Matt & James, Mentor Group

Most sales organisations underperform for reasons that have very little to do with their salespeople. Matt Webb, CEO of Mentor Group, and James Barton, Chief Solutions Officer, have spent decades helping global enterprises lift the bonnet on their sales engines, and the pattern they see again and again is that the issue is almost never just one thing. It is some combination of people, process, and technology, and trying to fix one of them in isolation is like playing whack-a-mole with the warning lights on a dashboard. In this episode they break down what is actually broken inside most modern sales organisations in 2026, why pipeline coverage at 3x or 4x has become a vanity metric, the difference between content consumption and skill acquisition, why so many enablement programs fail at the embed stage, and the order in which a CRO should think about investing in leadership, technology, and AI. Matt and James have just opened their first office in North America and have recently co-authored a new book, Infinite Selling. If you lead a sales team, run enablement, or sit at the top of a revenue org wondering why the numbers are not landing the way they should, this conversation is for you. CONNECT WITH MATT WEBB LinkedIn → https://www.linkedin.com/in/matt-webb-3b34ab9/ CONNECT WITH JAMES BARTON LinkedIn → http://linkedin.com/in/jamesabarton/ MENTOR GROUP Website → https://www.mentorgroup.com/ Infinite Selling (book) → https://www.amazon.com/Infinite-Selling-Approach-Generation-Realisation/dp/B0CKV4LB79 ▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬▬ 🎙 THE CEO AND THE SALESMAN PODCAST Subscribe for more episodes → https://www.youtube.com/@TheCeoAndTheSalesmanPodcast Follow Matthew on LinkedIn → https://www.linkedin.com/in/matthewwhyatt

Lessons from 30 Years Inside Big Business Transformations — Christopher Carter, CEO of Approyo

Most leaders believe their biggest threat is competition. Christopher Carter has spent decades inside some of the world's most complex scaling organisations and says the real threat is almost always internal. Complexity, dirty data, and the wrong technology in the wrong hands will slow a business down far faster than any competitor ever could.Chris is an author, keynote speaker, and one of the most experienced voices in enterprise technology and SAP implementation globally. In this conversation we get into the messy reality of what actually happens when businesses try to scale their systems without first getting the fundamentals right.WHAT WE COVER— Why complexity is the real enemy of growth and how it sneaks in through the people, not just the technology— The stair-stepping framework Chris uses when walking into organisations that have hit a wall— Why speed that makes a business successful at 10 to 50 people becomes a liability at 500 to 5,000— What actually happens when you plug AI into dirty, unstructured data— The most dangerous lie leaders tell themselves about growth— Why 97% of companies are failing to get ROI from AI and what they are doing wrong— What CEOs need to do before they even think about upgrading their ERP or adding AI toolsIf your business is growing but the cracks are starting to show, this episode is for you.Full links to Chris's books, upcoming tour dates, and speaking events are below.https://christophermcarter.com/Subscribe for more episodes: https://www.youtube.com/@TheCeoAndTheSalesmanPodcast Follow Matthew on LinkedIn: https://www.linkedin.com/in/matthewwhyattChristopher Carter: https://www.linkedin.com/in/christopher-carter-885159/

How to Increase Your Business Valuation Before You Sell — Digital Systems, ERP & Exit Strategy

When your business grows fast enough to outpace its own systems, success becomes the problem. Mark Batina, CEO of Precise Business Solutions, has spent 30 years walking into companies at $10M, $60M, $100M+ and finding the same silent crisis: the expertise that drives the business lives entirely inside a handful of people's heads, and you cannot scale a person.What we cover—What it actually looks like when a business grows beyond its own systems—Why the "linchpin" people in your business are both your greatest strength and your biggest fragility—The real reasons digital transformation projects fail (it's not what you think)—How systems maturity directly shifts your valuation multiple when you exit—The AI conversation every founder needs to have — and the one most are getting wrong—What it feels like when a founder finally gets their business running without themWhether you're at $5M or $500M — if all roads lead back to you, this episode is for you.Chapters00:00 Introduction00:53 What breaking actually looks like inside a growing business05:01 Why it's a complexity problem, not a revenue problem05:30 The expertise transformation framework — where it came from10:03 The knowledge multiplier effect and what smaller businesses can do now15:54 Why most digital transformation projects fail24:19 The founder as bottleneck — signs and solutions30:00 Valuation multiples and systems maturity — what buyers actually look for36:04 The most expensive mistakes founders keep making44:57 When a tech project sends a company backwards49:17 AI — what to tune in to and what to tune out55:42 What it feels like when it finally clicksSubscribe for more episodes: https://www.youtube.com/@TheCeoAndTheSalesmanPodcast Follow Matthew on LinkedIn: https://www.linkedin.com/in/matthewwhyattMark batina: https://www.linkedin.com/in/markbatina/?originalSubdomain=au

From Mowing Lawns to $3M Exit: The Sales Mindset That Builds Real Businesses | DJ Carroll

What separates entrepreneurs who build real businesses from those who stay stuck?In this episode of The CEO & The Salesman, Matthew Whyatt sits down with entrepreneur, speaker, and author DJ Carroll to unpack the mindset, systems, and sales principles that actually drive growth.DJ’s journey started when he turned down eight football scholarships to start a lawn care business. That decision led to building a company that reached $3M in revenue before selling, and eventually to coaching entrepreneurs around the world.This conversation goes deep into the real mechanics of building businesses today. Not theory. Real lessons.DJ shares:• Why most entrepreneurs misunderstand growth• The sales mindset that separates hunters from the hunted• The mistake founders make when they say they “just need more leads”• Why follow-up wins more deals than talent• The leadership habits that actually scale companies• How AI is changing the future of sales and small business• Why entrepreneurs must develop urgency to winThis episode is for founders, sales leaders, and anyone trying to build something meaningful in today’s economy.If you're building a business, this one will challenge how you think about sales, growth, and leadership.Watch the episode from the link in the comments.Subscribe for more episodes:https://www.youtube.com/@TheCeoAndTheSalesmanPodcastFollow Matthew on LinkedIn:https://www.linkedin.com/in/matthewwhyattLearn more about DJ Carroll:https://hunterheadgame.comhttps://www.linkedin.com/in/dj-carroll-65589b21/Explore Allie AI platform:https://hirealli.com

Why Most Founders Should Make Funding Plan B

n Episode 34 of The CEO and the Salesman, Matthew Whyatt sits down with Ed Kang, Chief Strategy Officer at Startups.com, multi-exit founder, investor, author of The Cortex Circuit, and yes, gas station owner.This conversation goes deeper than tactics.We unpack:-When resilience turns into stubbornness-Why most founders misunderstand strategy vs execution-The dangerous emotional bias behind pitch decks-Why funding should be Plan B-How joy becomes a performance advantage-And what AI is about to disrupt in startup playbooksEd has advised hundreds of founders. He shares what he sees six months before a startup collapses, the blind spots founders ignore, and the mental traps that sabotage growth.If you’re building, raising, selling, or advising startups, this episode will challenge the way you think.Watch the full episode from the link in the comments.Subscribe for more conversations with founders, CEOs, and sales leaders:https://www.youtube.com/@TheCeoAndTheSalesmanPodcastFollow Ed Kang on YouTube and LinkedInLearn more at Startups.com