CEO and the Salesman: Why Most Sales Transformations Fail

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 rarely singular. It is some combination of people, process, and technology, and trying to fix one of them in isolation is nothing more than temporary patchwork.

They recently joined Matthew Whyatt for an episode of The CEO and the Salesman Podcast where 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.

If you lead a sales team, run enablement, or sit at the top of a revenue org wondering why your pipeline is telling a different story to your revenue numbers, this conversation is for you.

Check out the episode on YouTube here: https://lnkd.in/eJgKvjBG