“I appreciate you meeting with me,” Victor began. “I actually want to tell you in person that next Friday will be my last day. I’m putting in my notice.” He smiled somewhat apologetically at his manager on the other side of the desk.
Lauren’s stomach sank. Victor was absolutely her best rep. He lived up to his name, winning more deals than any other rep in the company. Out loud, she said all the right things that a sales manager should say in this situation. On the inside, her mind was spinning. How could this have happened? What was she going to do now? And why had this caught her off guard?
If you’ve ever been in this situation, your first instinct might be to ask, “Did anyone see this coming?”
In most cases, yes, the sales ops team should have been able to see the signs in the data that your best rep was about to leave. The pipeline building slowed. The deal sizes shrank. CRM hygiene deteriorates. Engagement with tools and guidance dropped off. The signals were all there weeks or months before the actual resignation.
But while this data is all very important, focusing on the missed signals can obscure a more important question: What does this mean?
2 business problems that lead to resignations
Not every resignation indicates that you have a bigger problem with your business. Sometimes people quit for personal reasons: a health concern, a spouse gets a job in another state, or maybe they won the lottery.
But when you lose a top performer, it’s always worth taking a look to see if you have a deeper issue.
In one scenario, you could have an HR problem. The rep got disengaged and checked out. HR didn’t flag it or respond quickly enough. That certainly happens.
But there’s also a second possibility that is far more consequential. What if the rep is leaving because they think their opportunities are drying up?
A company’s best reps are often the earliest sign of a growth problem. They’re the ones most in touch with the market, so they’re the first to feel it when something shifts. And if they sense that they soon won’t be able to meet their income goals, they’re quick to jump ship. If a top performer leaves (or even just starts to show signs that they’re considering it), it might mean:
- The territory is tapped out, and there’s not enough upside left to chase.
- The products or services don’t align with what buyers are asking for.
- A competitive shift is making it harder to win.
- The comp plan doesn’t reward the kind of growth that’s available or doesn’t compare favorably with what competitors are offering.
In these cases, the rep isn’t really disengaged—they’re actually so engaged that they’re able to read the market more accurately than leadership is. They’re not leaving because they’ve lost motivation. They’re leaving because they don’t see a path to growth. That’s not a retention problem.
It’s a canary in the coal mine.
So which is it?
Sales ops is uniquely positioned to determine if you have an HR problem or a larger issue with the business. The data can help you distinguish between a rep who’s checking out and one who sees the company is hitting a ceiling.
You can start by analyzing pipeline composition, win rates by segment, deal velocity trends, and competitive loss patterns. When the signals cluster around a specific rep, it could be personal. When they cluster around a territory, a segment, or a product line, that’s something much bigger.
We also have some resources that can help. Check out Managing Risk in Sales Ops, Making Sales Ops More Responsive, and The Fundamentals of Sales Intelligence
Losing a great rep always hurts, but a well-functioning organization can always overcome the loss of one person, no matter how skilled they might be. The problem is that sometimes the organization isn’t as well-functioning as you think it is.
Managing Risk in Sales Operations
Whether real or perceived, it's always best to take a proactive approach to managing and mitigating risk in Sales Operations. In this session, learn how to mitigate major sources of risk before they can manifest.
Making Sales Ops More Responsive
How do we design our sales models, systems, and processes to maximize ongoing responsiveness, flexibility, and agility? And how do we do it without sacrificing rigor, diligence, and accuracy?
The Fundamentals of Sales Intelligence
In Sales Ops, it's easy to feel like decisions are made in a vacuum. But the reality is that there are many sources of intelligence you can leverage to help the sales team sell more effectively, now and in the future.
