Jacob Kaplan-Moss

The Intersection of Tenure and Seniority

In a previous post, I wrote about when patterns of short job tenure might be red flags. (You may want to read that post first; this one builds on it.) I wrote fairly broadly, in a way that applies to most roles and careers pretty well. But that generalization misses some important nuances about the way that I think about tenure at the most senior roles – particularly Director/Executive-level management, and Staff-plus engineering to a lesser degree. In those most senior roles, a history of short tenure becomes more of a red flag, and I want to dig into that.

Patterns of short tenure early in a career are normal

At the beginning of someone’s career, I expect to see job-hopping. Most companies are terrible at internal career development, and even worse at scaling compensation as people’s skills and scope of work grow. This means that if you’re new to the industry and trying to maximize your compensation and/or career growth, you’re going to have to move around a lot. Let me explain what I mean with two contrasting approaches to the first six years of a hypothetical career.

  • Option 1: staying at the same job for six years. Say this hypothetical engineer gets hired as a Junior Software Engineer at a starting salary of $80k. They perform well and get the maximum possible annual raise of 10%. They get promoted twice, to Software Engineer I and then to Software Engineer II. This trajectory – a 10% raise each year, promotions every two years – seems to be roughly average for most mid-sized to large companies I’ve seen. That is, I’ve seen better, but not often.

    Result after six years: a title of Software Engineer II, making $140k.

  • Option 2: job-hop. Let’s start this hypothetical career at the same place: Junior Software Engineer making $80k. But instead of sticking around, let’s have this person switch jobs every 18 months. If they have strong results at each previous job, they can expect to increase their job title each time they move, and they can expect to increase their salary to an average level for that new title. Here’s what that trajectory might look like:

    • Year 0: Junior Software Engineer, $80k
    • Year 1.5: Software Engineer I, $120k
    • Year 3: Software Engineer II, $180k
    • Year 4.5: Senior Software Engineer, 250k

    As with the numbers above, this is a reasonable career trajectory – someone can reasonably move to a higher job title every 18 months – and these salary numbers are quite reasonable for these job titles. (If anything, they’re on the low side. See this post for more.)

    Result after six years: a title of Senior Software Engineer, making $250k.

The person who job-hops ends up making nearly double what the person who stays in place does. If both start looking for new jobs at this point, they both can expect to get offers at the Senior level, but the person who job-hopped will be coming in at the higher end of the Senior salary band. That salary band is often really wide – $200k - $500k is not an unusual span – so it’s not unreasonable to expect this discrepancy to continue to grow.

If you haven’t learned much about tech compensation, these hypotheticals may seem contrived – but I promise they’re not. It’s believable that a job-hopping strategy early in your career could double your salary versus staying put.

As hiring managers, we need to blame this pattern entirely on the heads of companies that aren’t willing to offer market-competitive salary and role increases to people who stick around. I’m completely fine with someone who wants to speed-run salary early – in fact, I encourage it. So a pattern of job-hopping early isn’t a red flag. Quite the opposite: it’s a sign of someone who’s smart, motivated, confident, knows how to get a lot done quickly, and understands their value. I want to hire those people.

Short tenure is more problematic in senior leadership roles

As roles get more senior, however, I start to get more concerned about short tenure. More senior leaders tend to work on larger projects with much longer time windows to judge success. For example: a staff engineer leading a migration to a new database engine; a director creating and staffing a new team; an executive engineering an acquisition. These kinds of projects can take months or years to complete, and then it could be many more months or years to judge success. So if I’m interviewing someone who’s been in a Director role, but only for 18 months, their track record may still be up in the air. It may be too early to judge their success.

Further, these kinds of senior leadership roles seem to get more difficult around the 2-3 year mark. New leaders come in with a blank slate and a set of fresh ideas and are often able to make substantial changes quickly. But somewhere around that 2-3 year mark, they start to reach the end of their first big project and have to wrap it up and move on. Finishing things is really hard, especially at senior leadership levels. Taking a promising pilot project and making it operational requires a sustained level of effort and focus that goes beyond “innovation”. Often in these final phases, substantial unanticipated blockers crop up, and leaders have to figure out how to deal with them. Compromises need to be made. Timelines slip. It gets hard. It’s not unusual for people to think about bailing at this point. When I interview someone for a senior leadership role, I want to hire someone I believe will be able to finish projects, even when they get hard.

Finally: the biggest impact these sorts of senior leaders have on organizations is culture change. A great Staff-plus engineer doesn’t just create better testing infrastructure, they build a culture that values testing. A CISO that merely builds a new security team doesn’t have nearly as much impact as one that infuses the entire organization with a culture of security. The best senior leaders have a track record of pervasive culture improvement, and that takes years. Someone with several short stints in senior leadership roles will not be able to demonstrate (to my satisfaction) that they have the skills to impact culture in this way.

For all of these reasons, I think it’s reasonable to be more concerned about short tenure for candidates with a history of senior leadership roles. I wouldn’t blink an eye at a candidate with a couple of back-to-back 18-month stints. But if I saw a candidate with that same timeline in Director-level roles, I’d ask some questions about it. This becomes more true the higher up you go. If I’m hiring a VP or CEO (and looking for someone with experience in those roles), I’d want to see someone who’s spent years in those roles. (Or have a reasonable explanation for why they haven’t.)

Is this a reason to “stick it out” in senior leadership roles?

Does this mean that if you’re in one of these roles, and it’s terrible, you should “stick it out” for the sake of your career? I’ll reiterate what I said in the previous piece: “If your job is terrible, if it’s making you miserable, you can leave”. I would never advise someone to stay in a role that’s making them miserable. I’ve been in one of these situations and had to leave after only about 4 months. That was absolutely a terrible decision if I’m only looking at the optics for my career progression, but it doesn’t matter: I was miserable, and the root cause wasn’t something I was going to be able to fix.

But if you’re in one of these roles, you do need to understand the realpolitik of the situation, and know that leaving these roles quickly (especially if it happens often) can be career-limiting. It’s worth considering the source of your unhappiness: if you’re wanting to leave because the job is getting hard in the ways I’ve articulated above, maybe you do want to consider staying.

It’s also worth considering the greater economic context. As we (likely) head into a recession, if staying put is an option, you may want to consider it. Will Larsen writes about this calculus in Downturn career decisions:

Folks will reasonably disagree with this, and I agree it’s an inequitable practice, but I have personally seen friends get filtered out of senior and executive opportunities for having “too many” short stints in their resume. Voluntarily moving roles right now increases your risk of joining a company shortly before your role is eliminated (or otherwise becomes problematic), creating a risk of multiple short-term stints. You can absolutely explain those stints, and a reasonable interviewer won’t penalize you, but my lived experience is that landing a senior role requires passing multiple somewhat arbitrary process gates. It’s valuable to minimize the number of process gates that hinder your progress, which in this case means reducing risk of short stints in roles by preferring role stability in this downturn

The key word here, for me, is “voluntary”. There are absolutely situations that get bad enough that staying is worse, but if you’re considering leaving because “the grass is greener”, you may want to consider the optics of that decision.

I hope these two articles have helped better explain when job-hopping might be a problem, and when it’s expected. As always, if you have questions, please feel free to get in touch!