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Has anyone worked at <20 person startup before? How was it?
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Once a few years ago as an independent contributor. I won't get into details because for privacy's sake, but it was <10 people for most or all of the little over a year and a half I worked there.
In short, it was a mess.
I accepted the job offer the because product they were working on seemed compelling enough and to be honest, because my resume was rather thin at that point and I really just needed to get a paycheck coming in again after the considerably larger startup I'd worked at prior (30-40 people, I want to say) ran out of runway.
My peers were great, being smart, interesting people who'd done (and were doing) cool stuff. The founder was another matter, being someone who got bored easily, loved to micromanage, got fixated on minute details at expense of the bigger picture, and sometimes seemed more interested in the glitz, cachet, and network associated with being a tech startup founder in the 2010s than doing the associated work. Predictably, this ultimately led to the company's demise despite its potential.
I don't regret the experience and that's not to say that every small startup will be like this, but the risk is relatively high, and I'd be hesitant to join another unless I had strong connections with most of the people working there, preferably including leadership.
I’ve worked at two small startups. One I joined at around 6 people and left at 20. Another I joined at 3 and it’s now 4. There’s definitely an order of magnitude less bullshit than working at a big tech company. But I’ve also seen a 100 person startup ran pretty well. That’s supposedly the threshold where the CEO couldn’t know any more people than that. So when looking for jobs I’ve always steered clear of a >100 person startup. It’s just less pay than big tech and, potentially, many of the same problems.
Too early and you’re taking on risk that fundamental things are unproven. Is there a market for your product? What even is your product? Can your leadership lead? Maybe you’re okay with that amount of risk. There is a sweet spot where the company has just started to get traction and they’re doing a hiring spree. At that point you still get to build a lot of fundamental stuff, but you’ve got a tail wind. Everything’s easy when the graphs are up and to the right.
I like an environment where I can learn as much as possible. That usually means early, really early. There’s no way I can be motivated to do my job if I’m just closing a bunch of everyday tickets month after month. Because I’m one of the first hires I got to build our entire web app, learned kubernetes (the basics), got more AWS skills, learned lots of new Postgres stuff, upped my prototyping skills, built an ML workstation/server and just this week finished off a GPU cluster project in a data center. I like being in the position to put my touch on everything. For example, when you SSH into any of our servers I put in an ANSI color ASCII art version of our logo in the motd. And the best part is, when you’re new to something your learn the fastest. And there’s lots to learn.
It’s not the right way for people that are just trying to maximize income. In my opinion you should not work at a startup because you think it’s going to get big and let you retire. 99% of startups don’t have that kind of outcome. You need to enjoy the work. Thankfully, the work is much more enjoyable than the alternatives.
I've also joined two startups, one as pre-seed employee 4 (murdered by COVID at 7 employees) and another as seed-round employee 8 (current role; 14 employees @ A). I also joined two "startups" of 30-50 people (series C and B, respectively). I think @teaearlygraycold has the most nuanced take in this discussion but I wanted to add a few things.
Fundamentally, startups are about asking the question "do people want to buy this thing?" Sometimes, the answer is no and they fail. Rarely, the answer is yes and everyone is happy. Most often, the answer is sort of, but not the exact thing we built and we have to change some fundamental aspect of our business. It's this last part that most startups struggle with and it's called product market fit or PMF.
Every time a company doubles in size up to about 150 people, it's a completely different company. At 5 employees, everyone is everything. The likelihood that one of the founders is committing code before a sales call is very high. The lone engineer is working hand-in-hand with the first customer and the CFO soliciting feedback on designs. Day 1 at work is "get a code repository and a CI pipeline set up." At 10 people, the founders are probably focusing on sales and the 2-4 engineers in engineering are maybe making their first major iteration on the first minimum viable product. At 20 people, there's an org chart and maybe a filled out C-Suite of people. You might have a product manager. The engineering team is struggling to break down silos and even talk to each other. It is likely that the company has still not found PMF. In the 40-80 range, you're probably doing great! There's a lot of traction but you maybe haven't figured out how to cross the chasm. At 160 employees, congratulations, you probably aren't a startup anymore! There may be a funding around but the mission isn't "does anyone want this thing" but rather "how do we sell a LOT more of this?"
Every person at a startup has an outsized impact in a startup because there are too many hats and too few people. This leads to the learning that @teaearlgraycold discusses. My first stint at a pre-seed company fundamentally changed me and launched my career. I initially joined the company with a 1% stake and a salary of $120k in 2018. In 2021, I was making $45k and had a 3.5% stake of a now-worthless company. It was the most heartwrenching, stressful, fulfilling, engaging, technically and emotionally challenging, time of my life and I learned so much. When applying for the next job, in late 2021, my experience let me increase my base salary to $175k (and some other stuff). Fundamentally, every company pays you twice: there's the paycheck you get to put food on the table today and the skills you get to put food on the table tomorrow.
It also means that the interview is really, really, really important. That guy who's an asshole? You can't not work with him- he's the person who does those 5 things and has no real manager to speak of! Interpersonal skills- the management of humans and relationships, plus setting expectations and communication- plays an even more outsized role in a startup. How do you get people to listen to your insight and integrate into their insights? How do you get their insights? Are these roadmaps even remotely viable or are we throwing everything away in a month or two on the next pivot? How do I get John to not be a raging piece of shit? Startups do not fail because technology didn't work. They fail because of mismanagement and poor communication.
If it's really early everyone's expected to need to learn a lot. So the question is, how quickly can you learn just enough about k8s to deploy a service? And then once it's live learn a bit more about k8s to make sure you don't shoot yourself in the foot later.
How did you get your foot in the door at your first startup? I’ve applied to a few online but haven’t gotten any interviews. The fast pace culture of learning and doing is attractive to me but I can’t seem to break into it and find out if it’s for me.
Not the OP and things may have changed since I was in that position (mid-2010s), but for me it mostly boiled down to applying to as many as possible, even those I wasn't particularly interested in, to basically play the numbers game. Some number of applications led to phone interviews, the first few of went terribly but allowed me to find my footing which then eventually led to landing in-person interviews (which also needed to be mastered), and after a several weeks of non-stop grind, one of the in-person interviews finally "clicked" and I got hired.
It's likely an experience that varies a lot between individuals, though. My role is technical (developer), and at the start of the process, I had no credentials and my resume was very weak, with nothing but personal tinkering and a couple of small one-off gigs listed. For someone in sales, customer support, content, etc it might be entirely different, and someone with e.g. a relevant degree, certifications, etc is probably going to have an easier time earlier on than I did.
I used TripleByte, which was a recruiting firm that tried to find “hidden gem” candidates that wouldn’t do well in typical resume screens. They shut down a few years ago, but their CMO is trying the idea again under the name “OtherBranch”.
My last job was like this! Overall, a great experience but I imagine the quality varies more widely than larger companies. The environment can change a lot each time a person leaves or joins--but this is true on some level at larger companies too: one individual can make your life heaven or hell.
I think the added stress of working in a small startup is not worth it unless you are one of the founders. The workload can vary a lot too, depending on how management sees the company (are they planning a product pivot?, etc). Good leadership will know to not demand pointless busy work when they'll need all-hands-on-deck in the upcoming months.
I've been doing tech stuff for... a while. Last 10 years for 2 startups both between 5 and 8 people. Before also only smaller companies, but whenever they got acquired I've always left quickly (Every company I ever worked for got acquired while I was there, it sucks).
There's very little bullshit going on, no meetings about insane things, people who aren't competent just don't end up/survive in this setup it seems, it's a very personal connection to everyone, I don't care about "career", and there isn't one when the tech team is 3 people, just the ability to do your job well.
To be fair, there's less knowledge, and sickness/holidays do affect things... But I wouldn't want to have it any other way.
I have always preferred smaller companies and also been CTO in a startup with only 4 people. In startups, everyone gets a C-title. Silly titles aside, it does provide a great level of freedom and a great way to get experience. And as you have observed, much less stressful because there is practically no dumb corporate bureaucracy or chain of commands to worry about. The time from idea to implementation is very short, so you will spend most of the time actually doing stuff on the product and not much meta-work that will often creep up in larger organizations.
Of course the downside is the risk. Fewer people to handle emergencies, the constant threat that the company will go bust any minute and the focus for getting features out the door will often get in the way of designing your product with the best practices in terms of design, testing and safe deployment.
No recent experience. Back in the dot-com era I worked at several startups. Each was pretty different, but overall I learned a lot, I liked my coworkers, and it was never insane hours. I enjoyed the experience. None was a huge success, but one got bought out after I left and the sale gave me a nice bonus.
Working at a startup when it’s failing to find funding isn’t fun - a gloom sets in as management keeps talking up the next opportunity and people stop believing it.
After that I went to work for Google, which was a very different experience.
My advice is if that is what you hearing, then stay away from startups unless you stumble across a group you REALLY like and a project you are REALLY interested in.
Go in with the expectation that the startup will not make it, most do not.
Do it while you are young, don't have dependents, fewer obligations, etc. Count on only getting a pay check, some fun work ( why do it otherwise? ), and not much more ( no 401Ks, benefits, etc ).
Reading your post made me realize how fortunate I was with my small startup.
It only lasted a year, had no real benefits, but it was fun. It was 6 people. The owner was a very decent person and a pleasure to work for. They sysadmin guy was a bit of jerk. The rest were fun loving and fun to work with. We had our tables pushed together, encircled it with our laptops, talked and laughed while we worked. It was very casual. We got some stuff done. We only worked about 8/9 hours a day. The owner was even decent enough to give us plenty of notice when the company would be liquidated so we could start a job search if we wanted to. I was happy to hear that much later the own was able to sell part/all of what we made.
It all depends. I've worked at a series A startup (at the time maybe 12 people) where everyone got 3% of their salary as a 401K contribution. Not a match, just extra income.
I am currently at a very early stage startup as one of the first hires and have worked at another from 7 employees up until we were ~100.
As others have indicated. The experience varies from startup to starup. Two early stage startups will be very different even if they are trying to solve the same problem. This is because when the company consist of 5 people those five will have huge impact on what the company feels like. Once you start hitting 20-30 people I think there's a shift (and necessarily so). What works early on needs to be adjusted. At this point people are usually personally invested in the success of the company (and hopefully not only due to potential payouts). After this I think you'll stay to see diminished returns on hires unless there is structures in place for solid onboarding and a true company culture that people actually believe in. Once a company hits 100 employees I don't really think it's a startup any more. Sure, it probably sells itself to investors and potential hires as such, but at that point you either have a product with at least partial market fit or it's a failure.
Another aspect which I've been thinking about recently is the relative job security. At a startup with a 6 months runway you know that you won't have a job in 6 month ( unless you happen to succeed). Now you can either view that as highly stressful, "what am I going to do in 6 months?!?" Or, you can view it as 6 month of perfect security (as long as you are moderately good at your job).
As others have mentioned, doing a startup is probably not sound from a financial perspective. The startup is likely to fail. It can be a great experience (but on the other hand so can working at any company) and it is only as stressful as you make it. If you tend to worry a lot, have financial voes and little safety nets, then maybe go for a more stable job (if that's an option).
Finally, looking at Glassdoor reviews for companies with less than 50 employees (over its lifetime) is probably not a great indication of what your experience will be. For one, people who've had a bad experience is much more likely to vent. Reaching out to current employees and buy them a coffee might give a more nuanced picture. Then again if a few people have left a small company in a short time the job is probably going to be difficult due to the knowledge loss...
What constitutes a strategic deal for a startup with less than 20 people? I know 2000 people companies who would love anything above a five hundred seats at companies with about 5000 employees and 200 people SaaS B2B vendors that would love anything over 50 seats at companies 500 strong.
Frustrating. Performance is key to retention and expansion. It's all I had my guys focus on for like a year or two, until I felt like we had it dialed in.
Aside from actual runway, I wonder if it is true that startups have more security--even if you are the CEO. Startups follow trends just like any other company. If layoffs are vogue then some aspiring middle manager might try the old outsourcing to Croatia trick. Maybe he even knows that it isn't going to work but he does it anyway out of spite because you didn't make a good first impression to him.
Job security at large companies is illusory too: the company might have lots of revenue but they might have equally high costs. Especially fixed resources which might be inflexible to adaptation: a factory that can efficiently push out dadoods but not doodads. The company might be incapable of recognizing the changing market or be too committed to the strategy that worked for the last twenty years. Or maybe the new leadership team are all McKinsey alumni and they know how to gut the company to the ground in less time than you can say startup.
If you have a company with "aspiring middle managers" the company is probably out if the startup phase. It's probably past 20-30 ppl at least. If you are at that size and have started to look at cost cutting the company has already failed. You might be looking to grow by hiring in Croatia (which may or may not be wise), but firing people in a startup (if they can do the job) would look really bad and a surefire way to stifle your growth.
I think you have to be white and probably a man and you're gonna be doing senior software engineer to staff engineer level work. The stress levels are pretty high and it is not for everyone, certainly not for me. But that being said, you do absolutely learn a lot. There are a lot worse ways to spend time as a 20 something than in tiny startups trying to learn how companies are built.
Just, have an exit plan. That's something you learn early on.
Nitpick: On the West coast you could be white or Asian and a man.
As someone that's benefited from this stereotype I want to agree that this is certainly true. I've realized that throughout my whole career I've been able to walk into interviews and the default position is "Yeah he looks like he can do the job". I do still need to stay ahead of getting too comfortable. I need to keep getting better and gain experience. But there's a tremendous advantage to having people believe in you from the beginning and a tremendous disadvantage when from day one you need to prove you can do the job.
We only get so much influence in this world but I hope when I'm a hiring manager in the future I can make an incremental chip in that stereotype.
Yeah, I'm Indian. These days I'm not even sure being a 'model minority' is enough unless you're an H1B slave. I can't help but remind people that unconscious racial bias is gonna be an outsize problem with extremely tiny startups, since they're so risk averse.
You might be able to get by if you're Asian. But remember how the world works, a lot of really rich white people's fun personal hobby is being racist, often subconsciously.
My startup experience has been in the biotech/gene therapy sector. I held a position at that company for a little over three years before I decided to move on to graduate school. When I started there, I was just the 3rd employee to be hired, and by the time I left, the overall company had grown to ~15 people.
The initial experience was quite interesting- I literally helped to build a molecular biology lab from scratch (assembling furniture, installing the water purification system, establishing protocols for brand-new equipment, etc.) I put in long hours, but it didn't bother me then- I was learning new techniques & actually using my bachelor's degree in a way that felt meaningful. We had new ideas to bring to the market, we were funded out for several years with seed capital and grants, and I genuinely thought if we could actually develop product based on those ideas, the company would be successful.
Over time, though... it became painfully obvious that the people hired to be in R&D leadership shouldn't have been. They would frequently shift priorities in the lab, fail to communicate with others in the company about changes they made to projects, and engage in petty, near-shouting matches in the conference room if data they were presenting in a meeting was questioned. Several scientists burned out and quit after working themselves sick over a project, only to have that project scrapped by leadership. The misogynistic attitudes of one manager were frequently papered over by the CEO/co-owner (I suspect because they were members of the same religious community)...
So, yeah. Even with good base ideas & plenty of funding, the workplace turned toxic because of poor leadership and an unwillingness to actually address that toxicity. The company is still going, with a small market presence- but I wonder where it might actually be now if it weren't for the internal conflicts I was present for during my time there.
I was the first employee at a startup that grew to about 85 before starting to shrink again. Those first few years when we were scrappy and small were the most fun but also the most chaotic. Pay a lot of attention to the way the founder is because that will dictate how everything goes. The makeup of the rest of the team does matter, but the founder has probably hired people who are ideologically aligned or at least compatible, with their way of doing things. I had the advantage of having worked with the founders for a long time, so I knew what I was getting into.
My other piece of advice is this: being in early like that can make it easy to get overly invested in the product and the company. I ignored a lot of warning signs because a lot of my personal identity was wrapped up in being part of the company. When things got really bad and I finally did leave, it was more like a breakup (complete with sad song playlists) than quitting a job.
I'm not saying everyone will have this experience, but I think it's a risk especially if you are excited about the goals of the org. Try to find someone you trust who can help by providing some objectiviwAlso pay attention to the red flags. Don't talk yourself out of them. If the new HR person is closely related to the CEO, that is a red flag even if you trust the CEO.