Insight

Your Sales Problem Might Not Be a Sales Problem

Replacing the sales leader rarely moves the number. The cause is usually somewhere else.

Andrew Wildblood, Co-Founder and Chief Executive Officer · 18 September 2026

Having run sales teams for the best part of twenty years, I've seen the good, the bad, and the ugly. One thing stays constant: growth expectations remain high, even as almost everything that influences growth gets harder to control. Buyers are more informed, with more stakeholders expecting more from every interaction. Economic uncertainty has made decisions slower. AI is changing how the work gets done, while organisations are asked to deliver more with the same or fewer resources.

Sales is where strategy meets execution, where customer expectations, marketing, product, pricing, technology, customer success, and operations all converge. So when commercial performance falls short, sales is where the strain becomes visible first. The underlying cause is rarely confined to sales alone.

The revolving door

We're seeing chief revenue officers and chief sales officers given less and less time to deliver. The average CRO tenure now sits around eighteen months, against a CEO's average of four to four and a half years and a CTO's of roughly three and a half. Boards change the head of sales and expect a different outcome, from an organisation that's misaligned and resistant to change, expecting one individual to transform what the rest of the business hasn't moved on.

I've lived this. I was the third sales head in one business in three years. A few patterns kept showing up, and none of them were sales problems:

  • Product-market misalignment. The pitch reps were trained on didn't match what the product had become, so every deal turned into an uphill negotiation.
  • Pricing friction. Deals stalled not because reps couldn't sell, but because the packaging forced an awkward conversation at the wrong moment.
  • Broken handoffs. Marketing, product, and customer success each owned a piece of the buyer's experience. When those pieces didn't connect, sales absorbed the confusion, and the blame.
  • Trust damage from outside sales entirely. Competitors had moved. Operations weren't delivering. A security breach had cost us customer trust. None of it showed up as a line item under “sales,” but all of it showed up in the numbers sales got measured on.

What it looks like when it works

I've also had the opposite experience: a board that gave me the time and space to work systematically through every part of the business. Aligning with product to get the right offer for the market. Working with marketing to position it correctly. Building the sales team without compromising on quality. Building the investment case with the board to fund capability, product, and market expansion. That's what actually changes a company's trajectory, not a new sales leader parachuted into an unchanged system.

It shows up in smaller moments too, not just the big strategic ones. When operations and sales work in harmony toward the same customer outcome, you can feel the difference. Two executives sit around the table and align, it's fine to debate, even necessary, but the debate serves the better outcome for the customer, not two functions pulling in opposite directions to protect their own numbers. That's when brilliance happens: not when everyone agrees immediately, but when disagreement resolves around what's right for the customer.

Revenue is an executive responsibility

Improving sales performance isn't about focusing on the sales team in isolation. It's about strengthening the entire commercial ecosystem around them. The highest-performing organisations don't just build better sales teams, they build commercial systems where every function is aligned around creating customer value, and every leader understands their role in growth.

When the commercial system breaks down, the impact shows up in sales. But revenue is not a sales responsibility, it's an executive one, shared across the whole leadership team. Sales can own the number and the customer relationship. The inputs that determine whether that number is achievable come from across the organisation.

I've been on the inside. I've seen the good, the bad, and the ugly. If you're interested in how we can help you build the commercial system behind the number, get in touch with Caidence.

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