The Truth About Job Hopping in Tech Sales


The Truth About Job Hopping in Tech Sales

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Job hopping is one of the most misunderstood and misjudged aspects of working in tech sales.

After over a decade in the space, I've come to realize that it's a feature, not a bug.

I've been wanting to cover it for quite a while now...

I probably have 3 or 4 unpublished podcast drafts where I started to record an episode with my thoughts and then in the middle of the recording decided to scrap it and move on to a different topic.

Why have I been so reluctant?

For starters, job hopping can be a very polarizing subject in the industry.

But truth be told, the reason I've struggled to comment on it is because it's something that hits pretty close to home for me, and I'd go as far as saying I've developed a bit of a complex about it in my career 😬.

About 6 years ago, I had a recruiter tell me my resume looked like 'Swiss cheese', and that my tech selling career was 'most likely over' (I'm glad I ignored his feedback, otherwise, I would not be writing this today).

But sadly, I've been turned down for roles that I was excited about, with the feedback being that I have too many short stints on my resume and that they are looking for candidates with 'more longevity.'

It came up again recently when I was interviewing for my current role. My Founder expressed confusion that I didn't have any 5-year-long runs on my CV. Luckily, I was able to overcome the objection and secure the role (and I plan to stay put as long as I can to show some of that longevity 😏).

I get it, leaders want loyalty and a long-term commitment from the people they hire and overall, I think 99% of people want the same thing. But in reality, it doesn't always go both ways.

Plus, career success is typically not linear (especially in startup tech sales). Sooner or later, you are going to find yourself working somewhere where you are:

  • Trying to sell a product without Product Market Fit (PMF)
  • Subject to the whims of toxic leadership
  • Underpaid and/or undervalued
  • Living under constant stress or fear
  • No longer learning or growing
  • Completely burned out

On top of that, some data suggests that strategic job hopping can actually improve earnings since companies tend to pay more for new hires coming in.

So then, how does one find the right balance between staying long enough, but not so long that they lose out on career growth and earnings opportunities?

And how can short stints be reframed as a potential positive?

Over the years I've had a lot of conversations with: hiring managers, headhunters, and executive leaders to understand risk factors for sales candidates and what things they look for that scream 🚩🚩🚩

Some thoughts from my own experience, convos, and feedback:

  • Aim to stay at least a year. There are always exceptions, like toxic leadership or a company in financial freefall, but too many <1-year stints raise red flags and suggest you’re a flight risk.
  • Don’t stay too long either. Yep, this one surprises people. Some hiring managers pass on candidates who’ve been in the same role 5+ years, assuming they’re too comfortable or not looking to challenge themselves anymore.
  • VP turnover = rep turnover. The average VP of Sales in tech lasts about 18 months. When new leadership comes in, they often rebuild the team with reps from their network, so short tenures aren’t always your fault.
  • Startup reps get more leeway. If you’ve hopped around early-stage companies, hiring managers tend to understand. Startups come with chaos—M&A, leadership changes, shaky product-market fit, and unrealistic targets.
  • Job hopping is more accepted early in your career. In your first 3-5 years, moving around can actually be seen as a smart way to figure out what environment and leadership style work best for you.
  • It’s okay to leave for the right reasons. Better pay, a clearer path to growth, improved work-life balance, remote flexibility, or a title bump are all valid reasons to make a move.
  • Think of your resume as a narrative, not a diary. You’re not obligated to list every job you’ve ever had. I treat my resume and LinkedIn like marketing assets. If a past role doesn’t serve my career story, I leave it off.

So why share all of this?

To call out the fact that this shit is really hard!

Managing to be consistent in an industry that is always changing with growing targets, moving goalposts and a constantly changing guard is not for everyone, but that's why you're not "everyone," you're a Sales Player!

Take a step back and remember that this is just a game.

A former sales leader of mine used to say: "We aren't doctors saving lives, we sell 1s and 0s to companies... but if you learn to do that well, you can make more money than a doctor."

If you're struggling right now to know when it's time to make a move or you're having a hard time overcoming the "job hopper objection" in your interviews, then hit reply and let's have a discussion!

And remember that learning to manage this is all part of the experience.

Up and to the right!
- Jesse


Featured Episode: This Is Exactly How I Approach Cold Calls Every Day

Jesse breaks down the exact cold call routine he uses daily to drive pipeline.


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Sales Players is on a mission to reach 1,000 reps, founders, and operators in tech with FREE weekly content that explores the mindset, skills, trends, and tools used by the industry's top players to win at the game of tech sales.

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