There’s a conversation I’ve had with more than one Sales Director recently that goes something like this:
“We had one of our best reps leave. No warning. Just gone.”
When I ask what happened, the answers are almost always about compensation plans, opportunities elsewhere, or the usual “better culture” excuse. But the truth is often more layered—and more uncomfortable.
We’re not just seeing top performers jump ship for a bit more base salary or a fancy job title. What we’re seeing is disillusionment. The sense that the bar for great selling has moved—but the environment around them hasn’t kept up. And it’s costing companies their best people.
So the real question isn’t why they’re leaving. It’s why they’re not staying.
- High performers want more than money—they want momentum.
It’s easy to assume a top rep leaves for better pay. And yes, money matters. But most top tech sellers aren’t just coin-operated—they’re growth-driven.
What I hear from reps who’ve left is rarely “I wasn’t paid enough.” It’s:
- “I was carrying the number, but nobody cared what I needed to get better.”
- “I kept hitting target, but there was no talk of promotion or a new challenge.”
- “The company celebrated the wrong people.”
Top performers are usually the most self-aware. They know when they’re plateauing. They know when they’ve outgrown the role. And they’re acutely aware when no one around them seems to notice.
Sales leadership often makes the mistake of doubling down on what’s working—but forgets that what’s working for us might not be working for them. We tell them “Keep doing what you’re doing,” when they want to hear “Let’s find your next gear.”
The most magnetic environments for top sellers today? They’re the ones that combine recognition with reinvention. Not just: “Great job.” But: “What’s next for you?”
- Culture starts losing credibility when it’s not built for the best.
Here’s a hard truth: most sales cultures are built around the average rep. Which makes sense when you’re trying to scale. But it also means top reps are often treated like high-output machines rather than high-value individuals.
The moment your top performers feel like they’re being measured by the same lens as someone consistently underperforming—something cracks. You can’t build a performance culture if you’re not willing to differentiate.
That doesn’t mean putting people on pedestals. It means giving them what they need because of how they show up—not in spite of it.
Ask yourself:
- Are we creating growth tracks that are compelling enough for top reps to want to stay?
- Do our one-to-ones challenge them beyond deal reviews?
- Are we giving them visibility, stretch assignments, leadership exposure?
Because if not—someone else will.
What keeping your best people really looks like
Retention strategy isn’t about counteroffers. It’s not about adding another 5% to OTE after they’ve already mentally checked out. It’s about consistently asking:
- What keeps this person energised?
- What makes them feel seen?
- What are they building towards—and are we helping them build it?
One of the most underrated moves I’ve seen work? Building personal development into your QBRs. Not just “how did you perform,” but “what’s the next skill you want to master?” It sends a clear message: your growth matters here.
The companies who keep their top reps in 2025 will be the ones who don’t just reward performance—but actively invest in potential. Who don’t just build comp plans—but build careers.
Because when high performers feel they’re growing, they don’t start looking elsewhere.
They double down right where they are.
