The Rock Star Hire Who Wasn’t the Problem
We recently sat down with executive coach Piper Moore on our podcast, Whiskey Is for Closers, and she said something that stopped us cold.
We’d asked her how often a founder comes in thinking they have a sales problem — only for her to discover something else entirely.
“I think it always happens,” she said. “People come with what they think is the problem. But when you start asking those probing questions to get a little bit deeper into what it may be, you realize — maybe it’s not the salesperson. Maybe it’s your approach. Maybe it’s your tone. Maybe it’s what you’re bringing into the room.”
We’ve been building sales teams for founders at Altezza for years. In that time, we’ve placed talented, experienced sales professionals into growth-stage companies — only to watch some of them struggle, stall, and sometimes leave.
Not every one of those was the salesperson’s fault.
In fact, more often than we’d like to admit, the root cause traces back to something Piper talks about constantly: the leadership gap.
What We’ve Seen
Here are the patterns that show up — with uncomfortable regularity — when a placement doesn’t work.
The founder assumes the sales professional will “just figure it out.” Because they’re the expert. Because they’ve done it before somewhere else. Because that’s what you’re paying them for, right? What gets missed is that every business has its own context — its own market, its own buyer psychology, its own internal dynamics. A great salesperson brings a process and a mindset, but they can’t manufacture the foundation beneath them. Piper puts it this way: you can ask someone to execute a task from beginning to end, but if they can’t walk you through each step, something important is missing — and often, that something was never given to them in the first place.
The founder doesn’t know how to lead a salesperson. This one is more common than anyone wants to say out loud. Most founders became founders because they’re brilliant at making something — a service, a product, a vision. Very few were trained to lead a revenue function. So when it’s time to hold a salesperson accountable, they either avoid the conversation entirely or ask the wrong questions entirely. Piper said it best: “When I coach an employee, I walk them through the process — where are you missing a step? And then I look at strengths and weaknesses, because you may be asking them to do something they haven’t developed the skill to do — but they’re not telling you that.” A founder who doesn’t know how to ask those questions can’t close that gap. The salesperson just keeps grinding in the wrong direction.
The founder doesn’t listen. This is the hardest one to say, and we say it with empathy, not blame. Our Expedition Leads give guidance. Sales professionals surface what they need. And sometimes, founders hear it, and do nothing with it. The conversations happen. The recommendations are made. Monday comes and nothing changes. Piper identified this as the dividing line between clients who close the gap and those who don’t: “The difference is acceptance and willingness to change.” Not agreement. Not enthusiasm. Just a genuine openness to trying something different.
The founder keeps the best leads for themselves. We understand why this happens. Those relationships were built over years. They feel personal. Handing them to someone new — even someone excellent — requires a kind of trust that takes time to develop. But what it communicates to the salesperson is unmistakable: you’re here to work the scraps. And the math doesn’t add up. You cannot hand someone the bottom of the pipeline and expect top-of-the-chart results.
No strategy, no systems, no runway. Sales is not magic. It’s math layered on discipline layered on process. When there’s no CRM, no defined ICP, no pipeline structure, no clear go-to-market, the salesperson isn’t just selling — they’re building the plane while flying it, then being judged on whether it lands. Piper talks about the performance gap appearing “when you set goals and the employee thinks they’re doing everything they’re supposed to do — but because it was not clearly communicated, they’re really going down the wrong path.” In sales, unclear strategy doesn’t just slow things down. It makes success nearly impossible to measure, let alone achieve.
The business runs like a family, not a company. Culture matters enormously in a sales environment. When a business operates on insider dynamics — where tenure or personal loyalty determines who gets resources, who gets support, who gets the benefit of the doubt — the sales professional feels it immediately. They’re the outsider. They haven’t paid dues. No matter how good they are, they can’t win a game that wasn’t designed for them to win.
Sales Is a Team Sport
This is the thing we wish every founder truly understood before making a hire.
A salesperson is not a mercenary. They’re not a vending machine you stock with leads and collect revenue from. They are a professional who needs leadership, context, tools, support, and a culture that actually values what they do.
Piper said something in our conversation that we’ve been thinking about since: “In order to lead, you have to have people trusting in you. You come in with the wrong mindset and demeanor, and you’re already putting up walls.”
That principle doesn’t just apply to coaches sitting across from executives. It applies to every founder who has ever hired a salesperson and wondered why it didn’t work.
The high turnover rate in sales — across every industry, at every company size — isn’t primarily a talent problem. It’s a leadership problem. It’s a culture problem. It’s a systems problem. The salesperson is often the last domino to fall in a sequence that started much earlier.
What We’re Actually Asking of Founders
We’re not here to deflect responsibility. When an Altezza placement doesn’t perform, we want to understand why — fully and honestly, including our own role in it.
But we want to be direct about this: if you’re going to invest in a sales professional, you have to be willing to invest in yourself as a leader. That means learning how the function works. It means asking better questions and actually listening to the answers. It means building the infrastructure — even imperfectly — before you expect results from it. It means treating your sales hire the way you’d want to be treated in a new role: with clarity, support, and the real resources needed to succeed.
Piper closed our conversation with the one line she’d put on every leader’s monitor:
“Self-awareness and acceptance are the first steps to behavioral change and getting the outcomes and results that you desire.”
That’s as true for sales leadership as it is for any other kind.
The rock star you hired might not be the problem.
The question worth sitting with — the uncomfortable, necessary one — is whether you’re ready to look at what is.
Steve Caton is founder of Altezza, a fractional sales support firm that helps professional services firms scale past founder-led sales. Altezza works with founders, CEOs, and operators of $1M–$20M businesses ready to build a real Revenue Engine.
Piper Moore is founder of PM Morning and an executive coach specializing in the performance gap between leadership intention and organizational outcomes. Reach her at pipermoore.com.
