I worked in one for 6 years. The best thing was getting close to my coworkers, I’m still in contact with some of them to this day. The worst thing was the compensation. Can’t get more money when there’s none to go around.

Small companies are great. Opportunities for growth. Always the chance to switch to a bigger company later.

In my experience the micromanaging is LESS at a smaller company. No middle managers who have to justify their existence.

As you’ve already touched on, company culture is everything at small companies. If you fit in well, you’ll love it. If you don’t, you’ll hate it. I would ask to talk to other people in the company besides the CEO and talk to them about what working there is like and what kind of person would fit in well. If the CEO (I’m assuming that is who you are interviewing with) balks at the Idea, that right there tells you something.

I’ve worked at both small companies as small as about 12, all the way to massive fortune 100 companies (as a trans woman). Big companies get you many perks and often a very nice campus. But I’ve had better experiences mostly at the small companies.

The “boys club” thing never materialized too much, coworkers were decent people and I made great friends Never had a problem being trans at work. But the size definitely affects culture. Large companies have a fake explicit (not bad words, I mean explicit as in well defined and stated) culture shoved down your throat, small companies tend to have an organically formed culture. Big companies often attract leaders with high levels of narcissism highly driven to succeed and you have to deal with their tantrums. Startups attract unique people, still driven but in a different way.

One thing to be aware of at small companies though, is that many of these companies were formed for the purpose of being acquired, so their goal isn’t to be a cool company, it’s to do whatever it takes to be an attractive acquisition target which often sucks.

Even in a small company, the CEO is either going to be busy doing other things not managing IT, if they do manage IT, they would be no different than any other boss.

I’m in this exact situation now and have been for many years, while previously in a gigantic company…

Pros:

You (hopefully) tend to have significantly more influence on the tech stack and software direction. 

You're (hopefully) treated like a real person and not a cog in the corporate machine.

You (hopefully) get to learn and do a larger variety of things.

Cons:

Pay can be lower, and getting raises can be harder when you're talking directly to the CEO/Owner and it is quite literally coming out of his or her pocket.

Taking leave tends to be harder when there is so few people to pick up the slack.

the biggest downside imo is it can be hard to leave because you’ll feel more connected to everyone involved. but they won’t necessarily be able to pay you much more than you start at even if you do stay. and you’ll be spending that time on more or less the same tech stack which can limit your growth and make it harder when finding a new job later.

id say it’s fine especially as an early job but strongly consider a new job after 2-4 years

Pros: You get hands on with all sorts of tech and get to do everything. You’ll have more flexibility in how you solve things.

Cons: You get hands on with all sorts of tech and get to do everything. You’ll have more flexibility in how you solve things.

It’s fun being at a small software company but it can be exhausting.

Yeah, been at mine for 25 years now.

Pros: Good job security.

Cons: Not much money.

Pros: there shouldn’t be a lot of red tape or layers of middle management to deal with. If you have an idea, you know exactly who you have to convince to get them to buy in. Your contributions will have a visible impact right away. If you get along well with the team it may seem like too much fun to really be work.

Cons: resources will likely be scarce. The “IT Department” might just be Ed, one of the greybeard Linux guys, who maintains the servers in his spare time. (or worse yet, Ed might have just retired, and they think you’re the new Ed). There are only a handful of people “in charge” and if you don’t get along with them you may not be able to get much done.

I’ve worked at two smaller companies like that. I had a great experience at one of them, and a mediocre experience at the other one. So, I feel like it’s probably just hit or miss depending on the company.

Whether the culture is good or bad is not strongly indicated by the size. You’ll get a good feel by meeting them. Prepare some questions on turnover and overtime use. You want both low.

You will have to do work that in a bigger company would be specialist work. Some possible examples: Maintain infrastructure, drag network cables, purchase your computer, negotiate with service providers, software architecture, UX, product strategy, frontend, backend, integrations, customer support, QA, fix the printer, argue with the landlord about ventilation, etc. All this could be heaven or hell based on your personality. :)

pros - you can make a big impact and less strict processes.

cons - you cant just pass the buck and hide, you couldnt say ‘thats not in my job description’ just he ready to wear random hats when needed.

Very small is 3 people. It’s a small company.

My experience working in a dev company exactly that size -

Pros

Less dead wood (people not carrying their own weight).

Everyone knows everyone well, it’s a tight team

Think it, do it - quick to develop and respond

Less pressure

Feels a bit like a family

More chilled than corporate esp. working from home

More support of networking and linking up with industry peers

Higher degree of trust and support

Way more latitude to do what you want to do

Easy to influence senior leadership

Can offer things like equity etc

If you’re a high performer you will be noticed

Way less red tape

A lot more trust

Company can prosper if everyone works hard

Cons

Company favourites

Can be quite political, although far less so than some large organisations I’ve worked for

Less cover if you’re on leave or similar

Harder to get some things done if money is needed (lower budgets and thinner reserves)

Lower remuneration, fewer levers to pull to get a salary increase

More drama with paychecks etc

Fewer higher skilled people to learn from

Culture can go sideways quickly

Nowhere near the same level of support and benefits provided by the big companies

Tend not to attract the best and brightest talent

Comoany more impacted by economic conditions

It also greatly depends on you and your preferred style. Some people just outright don’t like working for big businesses and prefer smaller gigs.

Clique culture in small companies is pretty common. It might not be boys club but there’s no middle man to protect Devs from those in charge so there’s always going to be pressure to hang out if everyone is or to work overtime. You have to work in that clique culture but you don’t have to always say yes as long as you are friendly about it. The phrase “being firm” has never sight right with me for these as it’s the antithesis of friendliness you can be loose and say no and if it’s brought up again stay loose and continue to say no. You don’t need an excuse but a loose excuse is works well.

Security is obviously always scary but the tech landscape does not really have that anyway. Realistically if the only worry is it’s a small company and everything else is good, take it. If you find that you don’t fit into the small team flow, then you can continue looking in the future.

Some thoughts to keep in mind, speaking from my own experiences:

A small company is a higher risk in many regards, less ability to remain solvent during difficult times, less resources so more pressure on the smaller workforce, things like that.

From a dev perspective, you are also limiting the number of similar or better co-workers you could interact with which reduces exposure to things that came to them with experience that you don’t have yet.