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Should I Move To A Smaller Company?

Should I move to a smaller company? It depends on the risks you are willing to take.

Many of our readers work at large companies. After the COVID years employees realized they had more influence on their employers than they once thought. For those large companies that are not embracing change, employees are looking outside of their current employer’s open role list and finding that smaller companies may offer a better way to accelerate their career.

We are here to share thoughts on the benefits and risks associated with moving down-market.


Generally, these smaller companies need to compete on a broad range of benefits. They are usually non-cash benefits, but important none-the-less.

Let us start with the one big benefit everyone wants. Remote working. These small companies do not care if you are on the beach in Costa Rica or a mountain top in the Swiss Alps. If you have an internet connection and you are getting your work done, they could care less.

You will likely have tons of paid time off. It costs the company very little in terms of cash, but everyone universally seems to like time away from work.

Similarly, if you are moving to a technology, finance, consulting, or other professional services style company you will likely get equity as part of your compensation and if the company does well you can reap the massive upside.

💡 Pro Tip: When you are negotiating your offer, ask for more equity if you can. It costs the company very little and can really increase your overall take home compensation.

You will be closer to the leadership team and decision makers at the top of the house. Access to senior leaders is a big deal; especially if you are a top performer looking to accelerate your career.

Culturally, employees at smaller companies value getting to know each other and spending time with one another outside of work. These smaller companies will host more after-hours events, volunteering projects, and dinners (alcohol included).

💡 Pro Tip: Don’t get drunk at the company events; NEVER! Give a good reason, order water with a lime and act like it is boozy, or whatever but do not become an epicurean.

And let’s not forget the awesome break room freebies in the form of all the snacks and drinks your inner child could imagine.


Compensation may be lower and in the form of restricted stock units. So if the company does poorly you will earn less. There is an upside, but it comes with risk.

People are highly mobile at small companies. It seems competitors and new contenders are constantly looking to poach talent who has already solved a problem the new company is struggling to resolve. This could be a benefit if you are the one with the right skill sets.

However, if your colleague leaves, or even several people leave at the same time, then the team usually has to bear the burden for a long time until a replacement can be found as these companies usually run lean and mean with short staffed recruiting departments.

💡 Pro Tip: As a manager always have a replacement plan for people in those key spots or for those who have hard to replace skill sets.

Support departments are less seasoned and less capable, especially in supporting senior leaders, but they are all responsive and very friendly.

The new company could be bought, and new leadership could improve or decrease the value of your department or project.

In general the expertise, professionalism, and pace of execution are not as good as you would find at a larger company. Smaller companies just don’t have the money to pay for nice-to-haves and focus on the core business in efforts to increase revenue.

Thoughts on Managers

We don’t talk about managers and bosses in terms of benefits vs. risks. The reality is managers are equally bad, or good, throughout the general population. Bosses and managers are people too. They have external factors determining how they interact with the world; including their job world.

You are just a number when you work in a company of 50,000+ people. It is simply too hard to make sure that every manager in the company is good at their job.

Ironically, smaller companies struggle as well. There are going to be a lot of first-time managers. The “leadership” training you get at a small company may be well intentioned, but there is no replacement for sending someone through the crucible of large company management training.

It has been our experience that most managers and bosses are just not good at their job, or they were good once and life has beat them down so much they stopped caring. You can succeed in your role regardless of management, but always be considerate about your new manager when looking at a new role.

💡 Pro Tip: Always keep a lookout for good managers and hitch your wagon to that pony.

Final Thoughts

Moving to a smaller company can promote your personal well-being and make you happier as an employee.

Remember our advice on Preparing For Your Job Search. You need to know what you are looking for in your new company.

Just remember smaller companies are no better or worse than large companies, just different and those differences may just be the thing you need to accelerate your career.

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