Ask HN: How do you cope when your startup contracts?

The same general situation has happened to me twice now and I am wondering if it’s something I can break free from or if it’s just the nature of the Startup beast - or what. There seems to be some kind of bubble that starts drying up investment in a startup where I am a technical lead. Both times, things seem to be going well and then 2 years in there are rounds of layoffs due to factors outside my/product’s control where the result is the same. I end up as the last tech generalist. It falls to me to write as much of the code as I can, manage (if any are left) engineers in my department, running support basically on my own, owning a large part of the product roadmap, working with the customers on support and implementations, working with integration partners, plus a slowly expanding list of responsibilities as new stuff falls on reduced teams. I pick up new domains pretty quick (finance, insurance, compliance), switch contexts well. I’ve always been the person who just figures it out - someone who takes ownership of something and just does it. But, instead of being rewarded, I just get to keep my job while absorbing the work of others less fortunate.

During these contractions, the work never shrinks. Same clients, same integrations, same support volume (for now). Something else I’ve noticed is the scrutiny goes up - not down. I think a big factor is you have founders and upper managers stepping in to be more engaged or attempting to cover gaps. This causes all sorts of issues.

After this last round of cuts, the company offered me a revised title and job description that focused on managing the department that now was essentially just me down from 6 a year ago. It was full of responsibilities like “leading team to meet targets”. I did kind of want to accept it since it is the sort of role I was hired for and would help in a job search later. Regardless, I couldn’t because I am basically the team. It felt like a trap (or at least, wishful thinking that has been proven as much time and time again due to factors beyond my control.)

I could just leave, but the job market and economy look scary as hell. It took me 8 months to find a role last time. This is primarily due to my experience and background. I’ve been involved in engineering, product, support, sales, customer success, integrations and user comms. I look like someone who could/did do everything but that comes off as someone who owned nothing. The reality is I owned way way too much as things evolved.

Three things I am trying to think through and could use some help with:

1. Is it just the companies and bad luck? Am I picking startups in industries or with offerings that are just vulnerable to VC trends and hype? They both seemed like great opportunities, and I completely understand there is always risk - but the current/former result as it pertains to my role and situation once cuts were made is surprisingly identical.

2. Should I stand my ground? I have a habit of trying to work things out and get scrappy. During the last contraction, I spoke out to the president of the company that I wanted to sit down and look at our team’s responsibilities and projects that were being used/sold and see what was essential, could be covered, etc. That never happened - should I have been more firm and demanded it versus just absorbing it?

3. Ignoring the company, should I lean into the role and try to develop it? Should I accept I am an amazing generalist “jack of all trades, but master of none” and make it a more deliberate role/career? I know these sort of people are needed, but no company can really put out a role description for them. I’m seeing AI helps cover a growing amount of the gaps that I can’t dedicate the time to developing. I also have enough experience and knowledge to know AI is a tool and needs to be closely guided and applied in focused/appropriate areas. (Case in point - I’ve spent the last two hours fighting it from going off the rails in our Go golden test framework because it wants to ignore our test patterns).

I’m curious if others out there have found similar issues with Startups. Also, if there are other “Red Mage” technical folks that have a hard time in the job market because they’ve been asked to cover such wide areas?

14 points | by jasonephraim 1 day ago

9 comments

  • bruce511 21 hours ago
    >> The same general situation has happened to me twice now and I am wondering if it’s something I can break free from or if it’s just the nature of the Startup beast - or what

    9 out of 10 statups will fail. So if you're joining startups uou can expect them to (mostly) follow this pattern.

    If you don't like this pattern the perhaps look for jobs at more stable (ie non VC) companies. And consider companies not directly in tech.

    As regards to today, yes the job market is swamped. Don't quit your current job unless you gave something else to go to. But perhaps start actively looking.

    Given you're a generalist, it's likely you'd make a good fit in a company which has been around a while, and which has a reasonable "IT" department, as distinct from a pure IT company.

    • jasonephraim 13 hours ago
      Polishing off the resume. Thanks for the advice
  • tacostakohashi 1 day ago
    imho if you're at a company, and they're having layoffs... it's generally better to be laid off, get some severance, and end up at some other company that is hiring / growing, rather than a "survivor" who now has more work to do with fewer people at a company that is possibly troubled, unlikely to give any good pay increases any time soon, etc etc.

    re #3 - no, "jack of all trades" tends to be a career trap / dead end. companies hire for specific skill sets.

    • jasonephraim 13 hours ago
      Yeah there is always that thought like it would be easier if I was cut early - especially as they are usually more generous initially.

      Any tips on avoiding being pulled in too many directions?

  • toast0 8 hours ago
    > During these contractions, the work never shrinks.

    That only works so much. If a team goes from 3 people to 1 person, that's probably doable... you're leaving out a lot of communication. But from 6 to 1, you're going to have to prioritize what gets done and what doesn't.

    But if you're working for the payoff from equity and the team size is shrinking that much, there's no payoff coming. Your salary had better be enough, but you should be looking for an exit.

  • nehpets 21 hours ago
    You're not unlucky, you're just really good at absorbing pain. Companies keep you because leaving would break things. That's leverage... use it. Negotiate equity or walk.
    • jasonephraim 13 hours ago
      Appreciate the thoughts. If I am in a position like I describe, equity seems like the last thing I'd want. IMO the only real choices are walk, some guarantee of a team, or reduce the work.
  • slashnode 1 day ago
    The only reason to accept the negatives of working at a startup (stress, below market remuneration, workload) is the potential upside (rapid growth and an eventual liquidity event).

    If the startup is contracting, it sounds like the only potential upside has disappeared. I’ve been in a similar situation before and made the mistake of sticking around, to the detriment of my physical, mental and financial health. Obviously businesses pivot and turn around, but that’s the exception rather than the rule. Most startups fail, and if your startup is starting to falter, I’d say it’s about to prove the rule.

    I’ll give you the advice I wish I had:

    Run. Start interviewing like crazy and get another job. Good luck.

    • htrp 1 day ago
      sounds like you need to tell your CTO to lead more on the tech side or get enough equity to be an equivalent head of engineering level
    • jasonephraim 13 hours ago
      Heard. Thanks for the advice
    • toomuchtodo 1 day ago
      Seconded. You’re only there because it’s a rocketship. If the rocketship is out of fuel, parachute.
  • blowsand 21 hours ago
    Honestly only read enough of that to get the gist, but having been through many iterations of this over a couple decades of living a life in SV tech - you carry on. Each time you take away (hopefully) some improved sensitivity to the flags and signs that help guide your future decisions. That said, it’s also the nature of a fast moving industry to rapidly ideate-float-fund-fold.
  • DANmode 1 day ago
    Have you tried owning 40% or more?
  • Nicci-K26 13 hours ago
    [flagged]
  • corpusiq_io 19 hours ago
    [flagged]