It’s a two-edged sword for sure.

The good:

• Lots of room for creativity, innovation, and change. But as others mentioned, this depends on the company culture.

• Less red tape because of the shorter line up the organization.

• Faster promotion track if the company grows and you’ve already established yourself. You can also get a huge payout if the company is acquired in the future.

The bad:

• Possibly not as organized vs a company with an established support group (admin, payroll, HR, etc.).

• People having to perform multiple roles due to having fewer personnel.

• As a counter to the 2nd bullet in the pro section, having to deal directly with top management means you’re more exposed to politics.

• Possibly lower pay. But you said they’ve been around for 2 decades so maybe they’re paying well, and I’m sure you’ve considered the pay already.

Ok, I’ll give my experience. I was hired as basically a paid intern. I was in high school, I “knew” computers like a nerdy teenager knows computers… Not real knowledge of their workings but I played with some programming(I got hello world to work using perl) , I could install linux(in the early 2000s, I bought copy of Debian Linux on 7 cds). I was basically told I would be an assistant to the other computer technician.

A week after I got hired, he got fired. For the next several months people got hired and fired after a 2-3 weeks. The company was 3 people, myself, the owner, his wife did the accounting. I didn’t know what I was doing, googling what I could to figure stuff out(i now know that’s normal but also now know how to Google correctly). I leaned on the owner to figure out things. I don’t know if your job is in computers but these are things I learned later were absolutely idiotic.

1. If a computer came in with a suspected virus, standard protocol was no research or investigation… Format and reinstall.

2. We had corporate clients (main client was a credit union), we gave the windows CD and license code to each teller with no record of what they were. He sold the license at the price he bought then for from staples.

3. All servers had local admin accounts. All local admin accounts had similar passwords. I was the only person who knew what those passwords were.

4. My boss thought time spent documenting was time wasted.

Anyways I stayed there for 4 years. It was not perfect and I learned so much wrong stuff. It was a decent job, my boss had really weird rules(why so many people got fired), and my time would of been spent better learning correct information.

That said I ended up causing the company to go bankrupt and the owner and his wife are now Christian consulers…

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.

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.

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.

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 worked for a small software company for 6 years after finishing uni. I was the first person the founders hired. It was a great time and I learnt a lot and got to make a lot of decisions and had a lot of freedom.

But they didn’t pay anywhere near as much as a corporate job so when I got offered significantly more money to work for a very large company the small company couldn’t match it and pushed me to take it as a huge career and development opportunity.

It’s been great working at the big company but I really miss the culture and involvement I had at the small 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, etc. All this could be heaven or hell based on your personality. :)

I’ve done both large companies, small startups, did freelancing, anything for a paycheck. I now am a engineer for a major company with 10k employees and there’s so much that I picked up that would have made my life easier when I worked at a small company.

At a small startup, I absolutely was the jack of all trades developer. Everything from setting up infrastructure to web development. I was paid well but I didn’t feel like I knew anything. We were always in rush mode. I remember working 60hr weeks for months because we had so little revenue and we’re trying to save the company.

At a small company of 20 ppl, I was senior developer #3. There were only three developers. All seniors apparently, but paid like 30% less than our counterparts in other cities. The drama was so stupid. Everything was done because “That’s how we did it.” So much reinventing the wheel. The lead senior belittled and was a awful human. When I quit and joined my current job, he asked me for a recommendation. I still gave it, but he failed the first round of technical questions.

The cons of working at a small company?

• Too many hats.

• You are in charge of the domain. If you take two weeks off, you will get phone calls.

• It’s only as good as the experts involved. Good Project managers and testers are a godsend and may not exist in small companies.

• I was paid well but being in revenue talks and the “we have two months of runway before the whole company shuts down” is so incredibly stressful.

There’s pros too. But at my experience level and current lifestyle, I love turning off my laptop for the day and coding my own stuff on the side.

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.

I worked in both small and big companies.

That “micromanaging CEO” can also happen in big companies as your skip-manager doing that. So, being in a big company isn’t a safe bet against it.

I would say there are more pros than cons in working for a small company. Especially if you’re at the beginning of your career.

What you should make absolutely clear is that what you’ll be working on i.e. products & technologies.

Pros:

• You may learn a lot of things. Not only on the tech side but also about how to deal with people, how a project is managed, how business is translated into tech.
• It’s easier to be seen and heard. You see a problem with a business initiative, you can convince the managers and change it to avoid a certain disaster. Your achievements will be recognized more.
• Less bureaucracy. Big companies move very slowly. Also with your career development. You will have to jump through many many loops to just get a pay raise as much as the inflation. In small companies salary adjustments and promotions are much faster.
• You may rise up quite fast. With the allure of big companies stealing talent from small companies there may be many opportunities to grow into different roles in the company.
• Small companies need to retain their employees more than the big companies. It’s an expensive and time consuming process to hire. So a smart small company will try their best to retain its employees. If the financials of that company are good it means you will have better job security.
• Less playing politics. In big companies there are a lot of times you have to play politics against other teams to get something done. That’s tedious and time consuming. You may see the work you spent so much time on to be “postponed” to another quarter just because some other team “wasn’t ready yet”.
• In big companies there are a LOT of legacy, badly written, big riddled, failing code present. Most likely you will have to maintain code like that alongside new code. In small companies it’s less likely to encounter very bad legacy stuff.

Cons:

• If there’s a micromanaging CEO (especially without tech experience) this may drive you crazy. The same applies for an incompetent direct manager.
• It may be unbearable if you don’t “vibe” with the people. Especially if they are rude or insulting. In big companies how people shall interact with each other is defined and enforced. May not be the case in a small company.
• The salary may be lower than what you’ll get in a big company. But if you’re early in your career that shouldn’t be the most important point.
• After 2 - 3 years most likely you’ll learn everything in the company and it won’t feel challenging. Then you’ll need to change jobs as the things you can learn at a small company are limited to what they are using anyway.
• There will be a lot of focus shifts and last minute changes. Things will (almost) never go according to the plan. What you have been working on may be shelved due to changes in business requirements.
• Related to the previous point you may need to work overtime.

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.

A small company like that likely won’t have policies and processes to fall back on. This can be good for some things, but when things go bad it can backfire.

Mainly for things like promotions, HR, complaints, etc. In big companies there’s a formal process for how to get promoted and what’s expected at each level, etc. Same for HR complaints. At a small company you’re going to be more subject to the whims of whoever is in charge.

Same for new projects. In a big company you have red tape and processes to blame when something fails, but in a small company it’ll be more likely to be “your fault”.