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Why I Prefer Working at Startup-Like Companies as a Software Engineer

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July 8, 2022

I recently wrote an article about working at super corporate companies and why I won’t work for them anymore; if I can help it. Here’s the article:

Why I Won’t Work for Super Corporate Companies Again as a Software Developer

A reader asked about the other side of the coin. This article will highlight the pros and cons of working for a startup, consultancy, etc.

Some Background

Out of 22 years in the industry, I have about 7 years of experience working at some form of startup or small shop that has gone past the 5-year initial startup lifespan; I have even built my own startup and ran my own web development shop long ago, but I’m not counting those years as they were run in parallel to regular work.

I’ve worked at a company that was building biometric security software and I led the ‘.NET’ department where we built desktop and web applications. It was a promising technology, but the company eventually lost its main investor after 6 years and shut down. Almost the same thing happened at a well-established company that put all its chips in on a social media platform and shut down its main business before finding out the platform was taking longer than expected. Long story short, shut down.

Now, I’m working at a company that’s been around for 12 years and over the last few years, I haven’t been more excited about a product or service. I was hired to rewrite their current application and build in new features. The team is small, but everyone is a solid developer. We have a lot of work and the client base is growing.

Why Small Companies?

Smaller companies are really appealing to me as long as their product or service is exciting. There are many pros and cons about working at places like this, but I feel the pros eclipse the cons, and a vibe comes with working at a small company. Let’s get into it with the cons first:


  • There’s a lot of work and a small team to do it. This can be stressful as you’re working on coding a massive list of features, getting it tested, and out the door before working on the next list.
  • There are no slowdowns or lulls. Because you’re working with a small team; it’s go go go. Time to market with a new set of features will probably be around every 2–3 weeks; not 2–3 months like at big companies. This is, in my opinion; a good thing… see pro #1 below.
  • Not a lot of requirements documentation depending on the company. You may get a mockup and a short bulleted list of what that feature will do. In my first startup experience, I had to decipher a drawing as the entire requirement.
  • There may not be a formal time-off plan. You may or may not get any time off and will be taking your laptop on vacation with you. In some cases, you may get “unlimited PTO,” which means take as much time as you need, but get your work done. If you’re anything like me, you’ll work your ass off for a few months before taking a vacation and still working.
  • You will take on more hats than what you were hired for. You may be responsible for project management, testing (if you don’t have a QA), deployments, dev ops, various tech stacks, etc.


  • There’s no shortage of work and release schedules are shorter. I actually enjoy this more than the longer release schedules at big companies as I won’t get bored or feel like I’m not earning my keep.
  • You have a small team you’re working with. You will get to know these people really well, will most likely hang out with them outside of work, and create a strong friendship that will last decades; I have two friends like that from other companies.
  • The pay is often higher and there may be bonuses. These companies want the very best developers and will pay a premium as well as quarterly bonuses to keep you from looking elsewhere.
  • Shares in the company and the potential to buy more. As the company value increases, so do your shares. I’m not talking about buying shares in the stock market, these are internal; you are becoming a private shareholder.
  • Company-paid health insurance. To go along with the higher pay, you may have your health insurance paid for you and your family. To a small company generating millions per year, it’s a small drop in the bucket to pay for this and leaves you with more money in your pocket.
  • You may have your own office and office hours. Your company may be a total of 12 people with everyone in their own office. You may be in earlier or later than everyone else and that’s okay as long as you’re getting shit done. You may also be in an open space where you can collaborate with everyone freely, but you’re most likely not gonna be in a cubicle.
  • Unlimited PTO/vacation. Instead of getting the obligatory 2 weeks of PTO, which can increase with a certain number of years at the company; you get to take time off whenever you need to. This is great as you can avoid burnout with frequent breaks and don’t have to save up your PTO for the end of the year.

Burnout as a Software Developer And How to Fix It

  • You will be super creative and will be pushed to the edge of your skillsets. You will learn new skills, libraries, and tools to build a new feature. You will create things that have never been done before and your capacity for god-level thought will grow exponentially. Think of the movie Limitless.

Finally, The Payout

There are all sorts of benefits to working at a small company, but more so for a startup as there may be an end goal. The sale of the company. So many smaller companies get bought out by their bigger well-funded competitors and those that have a stake in the company can become wealthy individuals or at least get a big payout, but you have to be mentally tough to get through the ups and downs of working in a small fast-paced environment with no shortage of work.

Whatever your motive is for working at a small company, or any company really; you will have pros and cons to deal with. It will all depend on where you are in your development journey.

What are some of the pros and cons you’ve encountered working for small companies?