Hopping too many startups in a row? | Hacker News Reader

Hopping too many startups in a row?

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The last 3 positions I've held have been SWE at relatively small startups. Within 2 years of being at those companies, big changes occurred prompting me to hop for job security (didn't secure next round of funding, C-suite got replaced, etc). For me, this is the nature of startups- fast turnaround and turnover. I thought this was normal until my last interview where a recruiter was looking for stronger explanations as to why I haven't held a position for 3-4 years recently. Being clear that it wasn't a positive sign to them. Is it really that strange, or were they maybe used to bigger company culture and expectations? Not going to risk my own security riding a sinking ship.

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I would not recommend that you go down with the ship but you will want to have a good story for why you switched so often. It's hard to see "1-2 years for the last 2-3 jobs" and not get nervous as someone hiring. Even more so if I hear "The culture wasn't good so I left" or something vague for all reasons of why you left. It's going to take a month or so before they are contributing to the team and then a few months to a year before they fully understand the platform they are working on fully, it sucks to invest that time and energy into someone just to have them leave after a 1-2 years.

The old adage of "If everywhere you go smells like shit then check your shoe" applies here. That's not to say you couldn't have worked at 3 actually bad companies that you should have left but it's at least a warning flag. I've had people with short job tenures back-to-back explain the reasoning and I've been perfectly satisfied with it but I've also had people give me reasons that sound very fake. Interestingly, the people that come across as "fake" are also the ones that give off a slight whiff of "I'm better than this job" or "This is only a stepping stone for me". Those things can both be true but if can't at least pretend to care then I'm not interested.

> I would not recommend that you go down with the ship but you will want to have a good story for why you switched so often.

I mean have the story ready but you'll likely never get a chance to tell it. In this job market this is a "screen out without a phone call" criterion. I think it's shitty but it will likely be very hard to get interviews with this sort of recent employment streak.

> I mean have the story ready but you'll likely never get a chance to tell it.

Potentially, depending on where you are interviewing. I didn't write off anyone with multiple short tenures when I did hiring earlier this year but it was a red flag that I addressed in the first interview.

It's not you, it's the recruiters.

There is a wide cultural chasm between the startup world and established companies. The recruiters I have come across have very little real world experience. They are merely ticking boxes as handed down to them by management. So if management wants to hire people with a "solid" track record, then your startup experiences are going to be viewed negatively.

When you hop, at least get promoted. That way it paints a better picture. If you can honestly say that job C has more responsibility than B and B than A (even if same title) that is good too.

One option is to work for a large company with more opportunities negating the need to hop due to it going bad financially and more room to go up levels etc.

>> When you hop, at least get promoted. That way it paints a better picture.

I mean, it does, but it's still got a good picture. It comes across as "I'll jump ship the moment a better offer comes along."

The problem with job-hoppers is that there are ones done for sensible reasons (I joined high-risk startups, but ultimately they failed, or got acquired or whatever) and ones who just treat the position as a placeholder until something better comes along, or until they get itchy feet etc.

It's hard during the hiring phase to tell the difference, so employers tend to err on the side of "why take the risk?" Especially in the current market where there are plenty of other applicants.

Neither side of this story is strange. You have a reasonable history. It doesn't match what they want to see. Neither side is wrong, and you can't please everybody. I'd say if you are looking to stay in one place for 4+ years, you need to start by staying in a place for 2+ years. If you are fine bouncing more than that, that is your choice, and anyone who doesn't like it wouldn't have been a good match for you anyway.

Here's the thing: you don't really get to see the consequences of your decisions until 3yr after you've made them.

While it's perfectly understandable why you've responded to the changing environment of startups, the lack of holding a position for long enough is a career-limiting move.

It sucks, but the world isn't fair.

> the lack of holding a position for long enough is a career-limiting move.

is it though? I see people hoping all the time. Sure you're bound to run into a situation where somebody will view that as a negative but the only way you can switch jobs every 2 years is if somebody hired you. Which means that by definition, there will be companies that don't care.

I guess in a tightening market you'll have more candidates without job hopping so you can use it as a criteria but if your company has legitimate vertical movement there's probably less to worry about. Of course though if you company staffs its ranks pretty entirely by hiring outside as opposed to internal promotion then you should expect to replace the role in a couple of years.

> Here's the thing: you don't really get to see the consequences of your decisions until 3yr after you've made them.

That's a weird thing about resumes... they're pretty much for life, so any move has to be explained/justified over and over again one or more decades later.

Any short-term quick win to get away from a bad boss of a few thousand $$$ could stop you from getting a great job much further down the track. Any move should always be thought of in terms of "how will this look on my resume?" (which won't show salary, office environment, etc.) and "how can I explain this?". "It was a good opportunity to learn about XYZ, which they didn't have at the previous company" sounds great. "I had to get away from XYZ" or "I wanted more job security" don't sound as good, especially if XYZ or the fact that the company was a startup with limited job security was evident from the start.

"Where" you are in your career also make a difference. In your 20's, fresh out of uni, you're expected to switch around a bit. No problem there. Still job-hopping every 2 years in your 30's or 40's - that's a signal to the prospective employer that you'll be here for 2 years, then gone.

Often I'll also see someone who was in a job long-term (10 years+) but then has bounced through a few since leaving. That's a different kind of signal and requires a lot more exploration. You clearly -can- settle down, but you seem to be struggling to do that - why is that? I've had folk who are in the "don't tell me how to do my job, I've been doing it for decades" attitude which can be hard for others to work with, especially when "we do it differently here."

Meanwhile I've had 10 years of experience before my current job, only one of which is longer than a year. It's the nature of startups. I don't think it was ever held against me. If anything, some were only evaluating FAANG-style experience (usually ex-FAANG managers), but I wouldn't qualify for those anyway.

I would say riding a sinking ship is a negative for an employee - it's a world of pivots and rapid change. You shouldn't be too loyal to an idea, and likely that extends to loyalty to a company. For a founder level person, they are expected to see it through to the end, and do graceful shutdowns when it is doomed.

That's more like contracting than a full time position.

Yeah, that's a better way of putting it. I actually have them on resume as contracting because 1 page resumes are abstractions. The details go into a 20 page portfolio. But if a company has 6 months of runway, I can't mentally consider it a full time position anyway.

The recruiter perspective has some relevance too.

A question in their minds is whether candidates have the tenacity to stick through ups and downs of a company. This happens very frequently and I guess the employers are trying to gauge whether people will up and leave the moment things get difficult.

it may merit some nuanced explanation when such a question comes up.

"the moment things get difficult"

What does that mean? The company on freefall? The company reversing WFH policies that are in your contract?

You have generalised a huge number of situations into one phrase and implied that employees should suffer it through. Would companies suffer it through "the moment things get difficult" with an employee if they had the chance of not suffering it through? No, they would just fire the employee.

You can only expect reciprocity in a business transaction. And that is what employment is.

I think this is an important perspective. That is, think about why the recruiter is asking and focus on how you address those concerns. With the experience you have now, you should be well placed to ask questions early to find the right fit for the long run. (Or at least that’s an angle I’d consider!)

I disagree. How many interviews do you think it takes for someone to realize lying yields better results?

When "things get difficult" is a catch-all of subjective nonsense and to paint it in a more charitable light is intellectually dishonest.

Whenever "things get difficult"—whatever that means—you can count on the recruiter not being around and is why their opinion does not count for much. Often companies will let referrals skip introductory recruiter call entirely. Recruiters are invaluable to form cohesive teams in a startup, but they're glorified secretaries for hiring managers at a large corporation.

Anyone that believes they can deduce a person's commitment to some abstract mission statement based on a few historical facts and a couple hours of interviews is not a serious thinker. It denies the genius 1000x engineer whom quit to move across the country and take care of a sick family member or two. And it denies people with the self-respect to say no to unethical demands by executives. This might be a minority of applicants, but claiming to hire the best necessarily means reducing the type II error rate to zero.

I never said theres a catch all meaning to difficult situations. Every one has to draw their own lines about it. I understand its in fashion to talk about RTO as a difficult situation and it certainly is for a large segment of employees but would it also be a difficult situation for a developer if they are asked to follow a coding style at work that does not conform to their own personal style?

Some might say yes, thats a difficult situation while others might say how stupid that is to make a situation out of that.

The point was, the difficulty levels can vary and employers would like to know where an employee stands so as to gauge fit with the ups-and-downs of a particular context of that particular organization.

Over 27 years I have worked at 8 companies. 6 were large to medium size publicly traded companies and 2 were startups.

The startups were very chaotic and when I saw them fail to sell the companies 5 times, fail to secure more funding, layoff employees, no raises, no bonuses, failure to listen to employees, I could go on and on...

My explanation if someone asks is that I thought they were good opportunities but I was concerned about my job security after all of the issues and more I listed above.

It's not _great_, but it's not the end of your career, either. Try to start establishing longer tenures going forward. You're going to be doing this for decades, so build your resume now while you can. I job-hopped four times in four years toward the beginning of my career (late 90's), and although I've been at every job since for much longer, I've had recruiters ask for good explanations for it even as recently as my last job search in 2017.

It sounds like they're looking for not you tbh, but it also sounds like you value something startups can't give you and should probably try to find a more stable boring company to stick with longer; instead you're just repeatedly risking sinking ships and reacting to it by leaving early.

2 years is actually fairly long in the startup world imo, most startups (by %) don't even last that long. The average across the SWE industry (not just startups) was hopping every ~2.5 years a few years ago, and I believe it's worse now. I only start to scrutinize if I see a pattern of several in a row of < 8 months, tbh.

If anything, I tend to judge people a little bit who stay in the same place more than 3-4 years in this industry. Staying somewhere that long you end up with very insular views and limited exposure to new tech and ideas outside of your bubble, and beyond that, I am a bit wary of someone who isn't motivated by the financial incentive of a diagonal upgrade every 2-3 years, or somehow doesn't see that potential. Being able to effectively advocate for yourself and by extension your ideas I see as an essential skill for SWE.

Also, I think failed startup experience is super valuable, perhaps more valuable in some cases than coincidentally riding a unicorn and now falsely believing that every little thing you did along the way (or your cherry-picked list of "favorite" things you did) is actually repeatable, useful advice and/or a blueprint for future success.

>> If anything, I tend to judge people a little bit who stay in the same place more than 3-4 years in this industry.

While I completely understand this point of view, I wonder if you are speaking as an employer or employee? If, as an employer, how do you cope with your 25% of your staff leaving every year? How do you build that institutional deep knowledge if your longest serving person has < 5 years under their belt?

I can really only view it from the view-point of an employer (so my comment comes from there.) Personally I've been in the same job for 33 years now (was my first job out of uni) but I've seen the company grow from 2 people to 50. Most of our staff have > 10 years with us, and a bunch > 20. They are highly skilled, and have a depth of knowledge about our products and customers that are unmatched. They earn salaries well higher than other companies would pay them.

50 people is of course very modest success - I'm not saying we're a unicorn, or even especially valuable. But from our view-point we're also not looking to hire folk who have short-term goals and are already looking for the next gig down the line. Obviously lots of job-hopping is a red flag for our recruitment process.

And that's the thing I guess. Another company would have a very different perspective, and be looking for a very different kind of person. And ultimately that's ok. We don't all need to fit the same mould.

I'll add that it was never common in my experience to get "real" details during the interview process from team members regardless of using a recruiter. Maybe it's only with my background, but I find out an actual impression the first week (processes, cross team interaction, gossip).

So you switched a company 3 times in the last 2 years and now you’re trying to do it again? That gives roughly 8 months per company. So you onboarded yourself, worked a bit and started sending the CVs again?

That sounds like a huge loss for the employer.

> Being clear that it wasn't a positive sign to them. Is it really that strange, or were they maybe used to bigger company culture and expectations?

The question they’re asking themselves: What is the chance that you’ll be staying with them at least 3 years.

Based on your CV: close to zero.

I think he's saying he has been moving to the next company within 2 years after starting a job. Not all 3 companies in 2 years.

Let's wait for them to clarify. If it's 3 companies in 2 years, I'd not bother them. If it's a third company where he's leaving at 1 year 11 months - it'd look completely regular / fine for me.

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