Ask HN: Ever been the last engineer at a failing startup?

As long as you're having fun, learning new things, and not missing out on a great opportunity it makes sense to stay. That being said, depending on your job market, it doesn't hurt to look around. You don't have a hard decision to make until you have another job offer on the table.

I’ve never been in this position but I have a family to feed so I know I would at least have another job in my back pocket, even if I REALLY believed in the company or the team. But I wouldn’t leave just because I was the last.

If you can, look for other opportunities. The best time to look for other opportunities is before you need them. It will also allow you to understand your job relative to other jobs, and this knowledge will give you a much clearer reasoning for your decision making.

I have been in a similar position. In case you stopped receiving your salary, you should bail immediately. If you are being paid, start preparing to jump ship while continuing to work.

Not knowing anything else, there's a good chance you know your position may be gone in the next 3-8 months... One man shops can do a lot, but for a tech startup of note it's a joke.

This window is the time to get your resume together, watch online courses on company time, and start using some hot new tech in some capacity at your job. Your time should be focused on building your resume and attractiveness on the job market, and to differentiate yourself from other applicants.

I was the second to the last engineer at a startup that dropped from 15 to 3 people. my boss was the CTO, who I worked with on the perpetually 6 months from release “idea”. I switched to work for marketing guy, and together we shipped an update to a published product that had fallen on bad times. The update did great business, leading us to hire and grow till the company employed 100 people.

How is the last engineer at a failing startup different from the first engineer of a 'starting' startup? You're in a startup, volatility is a given. At least a failing startup knows more than a 'starting' startup.

Yes I have. Are you one of the founders? No? Then get out, out, out, out.

A lot depends on what the founders are looking to achieve. If they are still trying to grow the business then this creates some opportunities for you to make technical decisions and push for some equity.

On the other hand if they are just looking to milk whatever profits are available and you are running round maintaining a lot of legacy code it could be career death.

In either case the standard advice applies, keep some savings, stay in contact with your former colleagues and keep your technical skills up to date.

Not the last one but I have been on a sinking ship. It's not a good experience. Definitely plan ahead and look for new options but talk to the founders.

Not seen this yet but: negotiate hard. Ask for whatever would keep you happy: hours, money, whatever. And don't undersell yourself!

Yes. I worked on an application to detect major events around a topic using the Twitter firehose. It created alerts for, eg, when the Ukraine changed prime minister, showing alerts for the event way before BBC and Sky news had the story online (if you're interested there's screenshots in my portfolio, https://mikemaccana.com, the app was called 'waves').

CEO kept saying we were funded and had 'infinite' runway whenever I (lead engineer / CTO) asked. I never believed him, and then one day he turned round and decided to shut down the company. We're still good friends, but I wouldn't go into business with him again.

I spent a couple of weeks cleaning up docs for if someone discovered the git repo in future as it was hinted he might get some contract help in once the CEO sorted out the finances. I don't think it's ever happened.

Not the last, but near it. Also not the first, but near it. There's a huge difference between the two.

In my experience a sinking ship doesn't start floating, so don't stick around for that reason. It was also depressing to be there after all my friends had been laid off or quit. In reality I probably stayed there two years too long, and it was because of the people I worked with.

Last year, I was working for a biotech startup that was doing lots of interesting work but not making lots of interesting profits. Somehow the founders convinced a big company to buy us, and we spent about three months transitioning over to the new company. All of us knew the company had been in trouble, so it seemed like this buyout was the sensible thing for everybody, and all seemed well. The old owners got their millions, we lost all of our stock options (of course), but at least we still had our jobs. We spent the next three months being absorbed into the new corporate behemoth, until the Tuesday before Thanksgiving last year. I got an e-mail the day before that there was a mandatory 8 AM meeting for all of the new employees. I showed up, we all got on the call, and it was a recording informing us that all three of our offices were shut down effective immediately, and we would be informed of our separation details by personal e-mail. I got two weeks of severance and was unemployed with effectively no warning just before a major US holiday. If something comes up, you should probably take it.

I have left three startups that seemed like they were going nowhere. All three still exist, in a stagnant sort of way, but the friends who still work there seem pretty depressed. It's amazing how long you can keep a lousy business on life support.

You'll be happier with something new, and it's much easier to find a new job when you don't desperately need one.

I was actively recruited out of my last company. I was the last person engineering in the company but not the last engineer. Over a dozen other people had left by the time I did. The management was somewhat dysfunctional the whole time; but somewhat functional. We were always a subsidiary of a larger start-up which is still in business. Even thought they wanted it to be a unicorn worth billions it has been valued at 100 million for over five years now. They tried several times to hire me into the first company but the management disfunction there was very similar. Most importantly the company hired a replacement and is still profitable, with its existing customers. I just needed a change and I didn't do the hard work of finding a job until I was actively recruited. Once I received a job offer I was countered at the exact same level (not better though!). It seems that I myself had gone stagnant. I like the advice from others, don't be a person at a small startup who doesn't own part of the company. Just don't.

I was the last engineer of a small startup (from 4 full-time employees + ~4 contractors). I stayed a year beyond everyone except the founder/CEO in an attempt to launch the nearly-ready service, despite clear red flags. I achieved the established technical goals multiple times, but it became obvious the product would never launch due to non-technical reasons. It was a big mistake from which I have not completely recovered.

I'd suggest seriously considering what you hope to achieve and what you can reasonably expect from several angles: Financial outcomes, career trajectory, and personal motivations to name a few.

A few relevant questions: Have the issues which led to the current stagnation been addressed? Does the startup have a product that has been validated and can produce sustainable revenue? If not, what is the likelihood of securing (more) funding? Are you being paid well (without considering any equity/options)? How will your decision to stay look to future employers, considering likely outcomes? Why do you want to stay? Because you enjoy it? The challenge? Responsibility/Obligation (and to whom)? Sunk costs? Ego? Hubris? Messiah complex?

If you do decide to stay, I would suggest setting concrete limits/criteria for when to move on, so you don't get stuck in a zombie company.

Startup, no, but I was the last engineer in an established company that had been around for over a decade and fell on hard times.

I basically spent the last two years building my own business, and learning. When my boss walked in with the expected news that the company was shutting down, I wasn't in the least bit surprised, and was fully prepared for it.

However, I discovered I had a lot to learn about marketing my own business and took another full-time job about a year later.

I've been maybe not the last but one of the last handful quite a few times. If you don't believe in the company or don't like working with the people there, there's no reason to stay.

If you like being there, and you think it could work, I'd say to look for three things:

First, think about if there is a "turning point" moment that you're working toward. E.g. are you close to shipping your alpha, is there a big show coming up that could realistically generate a lot of publicity, etc? There's always some deadline or artificial milestone but is there a real one that people are actively working towards and isn't just wishful thinking? Or is everything just plodding along waiting for a big break to just happen?

Secondly, do you have a few customers (or testers) that are very passionate about your product? You don't need a lot of them, but if there is one or two people that really love the product that's a good sign that it's a real thing.

Third, how has the company or CEO handled bad news in the past? Was it a surprise or did they let everyone know it was coming and try to prepare together. If they're not being honest about their trajectory and their funding it can be a pretty unpleasant situation, but if everyone is working together to right the ship it can be a positive and bonding moment.

Finally, I would say to make sure you set the ground rules with your manager or CEO about payment. e.g. "I really want to see this company succeed and I will do everything I can to make it happen, but I have my own financial obligations, so I won't be able to come in if I haven't been paid yet for the previous pay period." etc. It's extremely common for people to go weeks or months unpaid and then the company goes dark suddenly and you're left without recourse. This is not even due to shady people or fraud, it can be good, well intentioned folks that think they have a solid line on more funding that falls through, or just aren't tracking finances carefully enough.

You should see it no differently than any other stage of any other gig: look after your own interests first since no one else is going to. Do you have better options elsewhere? Then jump ship. What's in it for you to stick around? If nothing, start looking since you're likely to be out of a job soon anyway. If they're asking/expecting you to go above and beyond to try to turn things around, what's in it for you to do so? Without a sizable equity stake (i.e. being a co-founder... and even then, the equity isn't sounding very appealing given the current situation), the only question you should be asking is 'what's best for me?' when considering your options.

Of course there may be non-monetary mitigating factors that only you can evaluate: do you really enjoy the work? Are you learning skills that you and/or future employers will value? Is it easy work for the money? etc. But considering the fact that they've already gotten rid of all the other technical staff via layoffs and attrition, you should be well disabused of any illusion of loyalty on the employers part. You owe them none. And redoubling your efforts is likely to make the endgame twice as painful for you if you stick it out.

Not exactly, but I was the only engineer at a small local publisher that was in transition of being acquired by a blue-chip company. But the transition seemed to be chaotic for the small company because they just had a blackout, causing them to lose days of work ahead, and the acquiring company didn't care and wanted to keep the goals as if nothing happened.

This lead to me putting out multiple fires related to one of the e-zines the small publisher had. I replaced the only developer who just greeted me on my first day and left. Clearly they didn't foresee how to budget for a tech department.