I’m struggling with making this decision at the moment and it was interesting to read this.
I’m not a founder, but I’m the first hire and the first engineer – there since day 2. Six years in, a couple of pivots, and now we have a team of 100 people with a gigantic series A just closed and an excellent PMF. I built most of the product myself – it’s genuinely game-changing and commercial demand is through the roof. Enough equity that if we were acquired now I’d be set for life.
But I just don’t know if I can hack it anymore. The commercial and product teams are pushing wildly unrealistic timelines for new features, which then the technical teams end up the bad guys for not being able to deliver on. Internal communication is all over the place, with nobody seemingly aware of deadlines and deliverables. The CEO is pretty visibly complaining about some teams not working hard enough, because he doesn’t see them in the office or working evenings and weekends. Meanwhile I’m on 18 hour days, under pressure to squeeze performance out of a team that I already think is delivering good quality at a pretty rapid pace, and being badgered constantly to provide KPIs and metrics for them so that the C-suite can deicide if they’re pulling their weight.
It’s almost exactly the opposite of the culture I’d want to create in an engineering team. Instead of teamwork and transparency aimed at producing a cohesive vision, everyone’s pulling in a different direction. Everyone is overworked and making mistakes, and instead of trying to build systems and processes to avoid these issues, it’s become a blame game. The answer to any problem always seems to be “work harder”, rather than providing the resources and support that teams require. Features are being rolled out to customers against engineering advice before they’re finished, meaning a massive drag factor as we scramble to patch them – and engineering leadership desperately trying to protect the rest of the team from having to pay for these decisions. And there’s this message being communicated from the top that suggests technical teams aren’t working hard enough that just feels utterly toxic. I’m probably making it sound worse than it is, but for certain the last six months have stopped being “I’m excited about working on this”.
How do you make the decision that it’s time to call it a day? Is it practically possible to shift the culture? Or is it feasible to detach yourself a little bit from it – concentrate on the areas you can change, and stop caring about those you can’t? I’m a well-paid engineer in an interesting field, and I’m invested financially and emotionally. It’s hard to be objective about whether it's time to quit.
Basically I can sympathise with the emotions you’re going though and thanks for writing about it. Hang in there!
I kind of hope you hold onto this throwaway account so you can tell us what you ultimately decide to do - from what you've said it sounds like the right course of action for you is to exercise your options to lock in your equity (assuming you have enough spare cash to do so) and move on, starting things off with a long vacation because you've been working crazy hours. Or you could start by just taking a long vacation and deciding what you want to do. Or a short vacation to work up to the long vacation - at the very least, a disconnect from the grind would probably really help.
I say this as an individual contributor though, and I imagine it must be tougher to consider walking away when you're a manager and you have a team of people who will be directly affected if you leave.
This reads like reasonably normal high growth growing pains. Miserable but common as everything is constantly breaking (not just the product but organizational systems and processes) as the company piles on new hires and new customer demands.
Communication breaks down completely as you leave the “everybody knows what everybody else is doing” stage and need to figure out coordination across siloed teams and work streams. Many people who were there at the smaller team stage get stuck in that mode of operating and it’s a painful push to formalize communications and build reliable/trustworthy systems.
Someone else mentioned this too but you should be past the 18hr/day phase now. It’s time to start building systems and spreading the work in a more sustainable manner.
Not sure what the situation is over there but it’s common to need to bring in a strong VP Eng who can help firewall the department, push back on unrealistic C-suite demands, counter strong personalities from other teams, and provide more stable prioritization. This is the most effective solution that I’ve seen when an eng team feels under the gun constantly, management is punching through to pressure individuals, people are feeling jerked around, etc.
> This reads like reasonably normal high growth growing pains.
Not the parent, but I don't see how this is normal. Your sales team giving customers high expectations is a recipe for customer disatisfaction. Releasing broken things binds resources on unnecessary things that would have otherwise been used to stabilize foundations or add new features. So you essentially have a sales teams sabotaging the plans of the engineering team by extorting them with things they promised to customers.
These are the signs of a dysfunctional and badly managed organization. Your sales guys should have a realistic image of your capabilities and customers should get things when the lead of engineering deems them ready. And if you don't trust their judgement on that, it is either a you-issue or a them-issue.
Completely agree with the ideal situation you present. The problem is that this doesn't hold up under the pressures of small teams chasing high growth.
Nobody is intentionally sabotaging anyone else (usually) but everyone stretches a little bit in the name of growth and things break down at the edges. Revenue growth can be life or death for small companies so, even though it sucks, promises are made and things are rushed. A perfect foundation and completely bug-free features don't matter if the business is dead.
There's a lot of sub-optimal juggling going on around this growth phase where you sometimes need to just focus on keeping the ship afloat until you hit the next set of milestones -> prove your worth -> raise -> grow the team to help shore up the foundation. Even if you aren't raising VC it can still be a similar grind where you need more cash flow to hire more to meet the exploding customer demands.
I will note that this only applies to high growth companies. If you have a pile of cash, strong product conviction (and skill), and the willpower to keep your feature set limited while turning away potential customers, you might be able to build the solid foundation -> sell the rock solid product. That isn't how most startups operate though and once you take VC the clock is ticking.
> Is it practically possible to shift the culture?
Yes. But it requires saying no to lots of things you used to say yes to (and vice versa), which can be extraordinarily difficult
It may not feel like it, but if you have been around since day 2 you’ll be respected enough to try anything you like, as long as you actually do it and don’t complain (not saying you’re a whiner but some people are). You basically have tenure.
Ask yourself if you're really that essential to things going forward? If not, then feel proud of what you've done and do what you need to do.
And I mean really ask yourself. As you say, teams are scaled now, individual effort has less of a multiplier. In most cases, they'll probably be fine without you. That should feel liberating.
the sense of frantic feature building is normal for a high growth startup. feeling constantly behind is also normal. a high growth startup is not a loving, nurturing, comfortable place. it's a mad dash for money and everyone is going to be pushing as hard as they humanly can, both in terms of work but also in terms of pushing others.
you're on the right track with the detaching yourself, but that can only get you so far. at the end of the day you still need to deliver things that sell. having people who don't know what the fuck they're talking about demand all sorts of wild shit from you is normal.
in the end, it's just difficult. you're being compensated with money and equity - if those aren't up to snuff, negotiate for more. if that doesn't work, you need to make the decision to stay or leave. there's a chance they give you what you want when you threaten to leave - and then you will have some leverage. but just realize this is not ever going to be a walk in the park. millions of dollars are on the line, people are not going to behave rationally because they see you as the limiting factor between them and their riches.
my comment is descriptive, not prescriptive. i doubt anyone even knows the difference anymore because of all the smarmy posturing these days.
"this rock is hard, and has sharp edges. it will cut you."
"no! that is terrible! rocks should be soft, with round edges! how dare you! nobody should accept rocks that are hard and sharp! that's dangerous! why do you support dangerous things?!"
No it's not, it's a false equivalence. What the original commenter described has way more pathologies than "startups are hard", and it does not smell like success to me. To pick up on your analogy, it's more like a rock that has been drenched in poop by someone, and you're supposed to use it to cut your food. There are other sharp rocks around, and most of them are not covered by poop, so you might be able to cut your food with it without getting a terrible disease and puke all food out again in the process.
Don't put words in my mouth. OP mentioned significant equity and the possibility to be acquired, without any details. This could both provide them with something to show after enduring all the suck, as well as with a real chance of changing management. If the question was to join the company, or no equity was at play (including if there's either no realistic chance of that equity being worth something, or if the equity does not lose its value for OP after quitting anyway), then yes, likely best to leave immediately.
Simplistic phrases are not going to help in complex situations with lots of details.
> because everyone is too mean.
No, because it sounds like a business bordering on dysfunction. You should know the difference.
I developed a very similar form for one of these sites. We were requested to and implemented features for safeguarding anonymity, like stripping information from web logs. The organisation insisted on including Google Analytics on the anonymous form submission page; I repeatedly made it clear that this was an awful idea, that this completely defeated anonymity, and that if usage data was required we could collect it in some other way. Unfortunately, I don't think they really care.
Security around this so-called anonymous data was thoroughly lax, and eventually someone is literally going to be murdered as a result of it.
I’m not a founder, but I’m the first hire and the first engineer – there since day 2. Six years in, a couple of pivots, and now we have a team of 100 people with a gigantic series A just closed and an excellent PMF. I built most of the product myself – it’s genuinely game-changing and commercial demand is through the roof. Enough equity that if we were acquired now I’d be set for life.
But I just don’t know if I can hack it anymore. The commercial and product teams are pushing wildly unrealistic timelines for new features, which then the technical teams end up the bad guys for not being able to deliver on. Internal communication is all over the place, with nobody seemingly aware of deadlines and deliverables. The CEO is pretty visibly complaining about some teams not working hard enough, because he doesn’t see them in the office or working evenings and weekends. Meanwhile I’m on 18 hour days, under pressure to squeeze performance out of a team that I already think is delivering good quality at a pretty rapid pace, and being badgered constantly to provide KPIs and metrics for them so that the C-suite can deicide if they’re pulling their weight.
It’s almost exactly the opposite of the culture I’d want to create in an engineering team. Instead of teamwork and transparency aimed at producing a cohesive vision, everyone’s pulling in a different direction. Everyone is overworked and making mistakes, and instead of trying to build systems and processes to avoid these issues, it’s become a blame game. The answer to any problem always seems to be “work harder”, rather than providing the resources and support that teams require. Features are being rolled out to customers against engineering advice before they’re finished, meaning a massive drag factor as we scramble to patch them – and engineering leadership desperately trying to protect the rest of the team from having to pay for these decisions. And there’s this message being communicated from the top that suggests technical teams aren’t working hard enough that just feels utterly toxic. I’m probably making it sound worse than it is, but for certain the last six months have stopped being “I’m excited about working on this”.
How do you make the decision that it’s time to call it a day? Is it practically possible to shift the culture? Or is it feasible to detach yourself a little bit from it – concentrate on the areas you can change, and stop caring about those you can’t? I’m a well-paid engineer in an interesting field, and I’m invested financially and emotionally. It’s hard to be objective about whether it's time to quit.
Basically I can sympathise with the emotions you’re going though and thanks for writing about it. Hang in there!