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If Your Sales Leaders Keep Failing, Maybe They Are Not The Issue

Beth Yehaskel · January 7, 2026

The average tenure for a VP of Sales is about 18 to 24 months. It’s only slightly longer for a CRO.

There isn’t just one reason for this, but in my experience there’s often a strong correlation between companies that struggle to find the “right” sales leader and the overall health of their GTM system. Which begs the question: is the problem that the leaders being hired aren’t the right people? Or is it that these leaders are being asked to succeed within a broken GTM system? It’s hard for any leader to be successful if the system is broken, no matter how good they are.

Here are a few things that consistently separate a healthy GTM system from one that isn’t functioning well.

Data-driven decision making. If you want to make informed decisions, you need to prioritize data. “You can’t manage what you don’t measure” (a nod to Cassie Young on that). That means tracking the right data accurately to set a solid foundation, and ensuring leaders use the right metrics to guide the business. Healthy systems don’t rely on gut feel, no matter how many years of experience a leader has. And a mountain of data and complex spreadsheets does not mean you are data-driven if you can’t extract the insights needed to understand what’s working and what isn’t.

A systems mindset and integration across revenue functions. Systems are interconnected, and changes in one part affect other parts, often in unexpected ways. A great marketing team, a great sales team, and a great CS team don’t automatically result in a great system. You have to design the system so these teams share goals, integrate their processes, communicate openly, and use tools that interoperate.

Repeatable processes. A healthy system provides predictability. You put something into the front end and you know what you’ll get at the back end. You monitor the output and adjust the inputs as needed. The system only works this way if you first learn what actions drive what outcomes and what skills it takes to execute them well. Roles, responsibilities, and workflows are all captured and clearly defined.

If you’ve struggled to find GTM execs who are the “right fit,” and find yourself replacing heads of Sales, Marketing, or CS every year or two, take a look at your GTM system before hiring again. Compare it against the points above. If you think there might be a system issue, may I suggest we chat before you go through the cost and effort of recruiting another leader who would face the same challenges? There is a better, and far less expensive, way.

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