Why CEOs struggle to understand sales - and what their background has to do with it

The importance of our background…

Whatever field of life, our early years are formative. Saint Thomas D'Aquin, an Italian dominican friar said: "Give me a child for 7 years, I will show you the adult". So the experience we have in early life forms the way we see the world.

The same applies in the business world. The experience we have in our early years define the way we see the business world. And this has a critical impact on the way CEOs understand the sales function. Or more often, doesn't understand it.

The CEO background

Mike Carrol wrote a book called "The Sales Team You Deserve: Why CEOs Tolerate Mediocrity and What YOU Can Do About It" (get it here). The tile might be provocative but Mike and I are aligned. There's often an acceptance of poor results (what Mike calls "mediocrity"…). And this is driven by the CEO's background, their vision of the world and the inevitable filters they have acquired.

From experience, these are the typical backgrounds we are seeing and how it affects their view of the selling function

The technical CEO

This is the CEO who is coming from an engineering background. He sees the world in a rational way, maybe a coding way or a manufacturing way. So this CEO would naturally think that a workflow or a process. Input / Output driven process.

The technical CEO might be also coming from a "PLG" - Product led growth - background and might be thinking: "Build it, they will come".

The consultant CEO

This CEO comes from a world where expertise is the product. In consulting, you don't sell - you get selected. Clients come to you because of your reputation, your firm's brand, or a warm introduction. The engagement is won in the boardroom with a PowerPoint and a methodology slide. Rational. Structured. Peer-to-peer.

So this CEO naturally assumes that if the product is good enough, and the pitch is smart enough, the deal will follow. What he struggles to understand is that selling is not presenting. That a prospect's silence is not agreement. That emotion drives decisions that logic then justifies. And that his salespeople don't have the credibility or the brand halo he had at McKinsey or BCG. They're cold-calling into a world that doesn't know them yet.

The finance CEO

This CEO sees the world through numbers. Pipeline coverage, CAC, LTV, conversion rates. Which is not wrong - but it creates a dangerous blind spot. He manages the sales function the way he would manage a balance sheet : if the numbers are off, something in the model is broken. Fix the model, fix the results.

What he underestimates is the human variable. That two salespeople with identical territories and identical tools can produce wildly different results - not because of process, but because of mindset, resilience, and the ability to sit in discomfort. You can't spreadsheet your way to a great sales culture. And when results disappoint, his instinct is to change the compensation plan - when the real issue is often upstream, in hiring or coaching.

The marketing CEO

This CEO has the advantage of being customer-aware. He understands positioning, messaging, personas. He knows what the customer wants to hear - in theory. The gap is execution. Marketing creates the conditions for a conversation. Sales has to have it. And having a conversation that involves rejection, negotiation, and navigating politics inside a prospect's organisation is a very different skill from crafting a campaign. This CEO often over-invests in tools, content and brand - and under-invests in the human capability to convert. He confuses awareness with pipeline.

The entrepreneurial / founder CEO

This CEO has been in the trenches. He often has sold, successfully in the early stages of his company's growth. So he assumes what he did can be replicated. Forgetting that the CEO title carries gravitas that his people don't. And that HE IS the company, has that natural drive and can, for example, articulate the vision. He has set-up the business based on this vision and the pains he, himself, faced. Forgetting sales people can't articulate this vision.

The sales CEO

This is, on paper, the CEO best equipped to understand the function. He has carried a bag. He knows what rejection feels like. He knows the difference between a qualified opportunity and a hope. But there is a trap here too. This CEO can become the best salesperson in his own company - which is not always a compliment. He jumps into deals, rescues opportunities, and inadvertently signals to his team that he doesn't trust them. If he coaches, which from experience is a rarity, it would be from his own experience, forgetting that what worked for him, as a CEO, or in a different market, a different era, or a different deal size may not translate. And because he is or was good at selling, he often underestimates how hard it is to build a team that sells consistently - without him in the room.

What they do miss…

Different backgrounds. Different blind spots. But there is one shared pattern.

Every CEO on this list has a filter. A lens built from their own experience, their own early wins, their own definition of what "good" looks like. And the problem with filters is that they are invisible to the person wearing them (which is why, when we talk to CEO struggling with sales, we turn the invisible into visible through our sales force evaluation)

The technical CEO optimises the process. The consultant CEO perfects the pitch. The finance CEO fixes the model. The marketing CEO builds the brand. The entrepreneurial CEO leads from the front. The sales CEO rescues the deal. None of them are wrong. But none of them are enough.

Because building a sales organisation that performs consistently - without the CEO in the room, without the perfect product, without a tailored market - requires something most CEOs have never had to develop : the ability to change mindsets and behaviour at scale. Not knowledge. Not process. Not tools. Mindsets and behaviour.

And changing this is hard. It is slow. It is uncomfortable. It doesn't show up in a dashboard the week after a training session. Which is why so many CEOs struggle to understand sales…