Short Stints, Big Questions: How to Assess Sales Executives Who’ve Jumped Roles

Hiring a sales leader is never simple – whether you’re trying to see beyond a charismatic exterior or make sense of a resume marked by multiple moves in recent years. It’s common for clients to dismiss executives with a string of short stints, and sometimes that instinct is right. Frequent job changes can point to poor performance, repeated missteps, or cultural misalignment. But today’s market demands a more nuanced view. The question for investors and CEOs isn’t whether to consider candidates who have “moved around,” but how to understand the story behind those moves and determine if the individual is worth your time. 

Why Today’s Resumes Show More Moves 

Frequent transitions are increasingly common. Demand for proven executives remains intense – these leaders are constantly being recruited and will sometimes take a risk on a company without an established product-market-fit or referenceable client base for a variety of reasons. For example, they may be itching to join a high growth company and shape GTM strategy and build a team, or they may be drawn to an equity opportunity or the chance to step into a C-suite commercial leadership role. At the same time, market realities have created turbulence. The softening of the market in 2023, shifting expectations around venture-backed growth, rising interest rates, and complex ownership structures have all contributed to moves that reflect circumstances rather than performance. The real challenge is distinguishing between opportunism, market-driven necessity, and genuine red flags. 

Effectively Evaluating Sales Leaders 

Evaluating such candidates requires rigor and nuance. A few tips:  

• Request high-level references. Ask the leader whether their former CEO, investor, or a board member will serve as a reference – why, or why not? Their response is an indicator of how their exit was perceived at the highest level. If they say no, especially after multiple short stints, this may be cause for concern. Yet even this approach must be taken with a grain of salt; some departures are confidential, contentious, or tied to broader market forces.  

• Probe for patterns. If the last three hops were attributed to “didn’t get along with the founder,” or “didn’t like the culture,” that can be a red flag. Some founders and cultures are challenging, so if it happens once, that may not be cause for concern. But multiple times? It’s very possible that the candidate was the problem and not the company. 

Ultimately, assessing candidates extends beyond resumes and timelines. The goal must be to understand whether moves reflect poor fit, poor performance, or instead adaptability and resilience. After all, an “A-player” can have a bad game if the company does not match their skill set.  

Finding the Right Talent 

Constructing the right recruiting process ensures hiring teams don’t waste time on candidates who aren’t a fit. Taking a targeted approach – prioritizing quality over quantity, applying market context, and digging into the nuances behind each move – is critical. By carefully vetting candidates to build a strong slate of five to ten, teams can optimize efficiency and stay focused on making high-impact decisions. Every hour spent on the wrong profile is time not spent advancing the business. Whether working with an external search partner or refining internal processes, cutting through the noise allows you to focus on what matters most: making better hires that drive results. 

Ultimately, short stints don’t always tell the full story. Sometimes they flag risk, but can also indicate adaptability, resilience, or external factors beyond a leader’s control. By asking the right questions, verifying references, and working with the right search partner, investors and CEOs can separate signal from noise and identify the leaders who will thrive in the organization and drive growth.