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What Size Of A Company Should I Work For?

Last Modified On: February 5, 2024, Author: Amy Sanchez

When pondering the next right career move, a common question that comes up is, “what size of a company would suit me best?”  I’ve worked for Fortune 50 companies, mid-sized companies, and a small start-up with less than 30 people.  So, if like Goldilocks, you’re wondering which one is “just right” for you, read on to learn about the nuances of each option to help you make the decision that's right for you and that can help you acquire the right type of leadership skills.

Smaller Company (Revenue $0-$10M)


  • Ability to see the immediate impact of your work
  • Working for a small company brings the opportunity to learn… A LOT
  • Less layers, easier access to senior management or support staff.  Presumably, less people mean less politics (although, this is not always the case)
  • Working for a small company comes with the opportunity for closer connection to the end-user in a smaller company (helps with real-time feedback and also, you can see the immediate impact of your efforts)
  • Can be very lucrative if your small company takes off (typically, a lower salary is balanced by access to a % of company ownership)
  • Very easy to stand-out as a superstar
  • Since it’s a small company, the employees tend to get to know each other very well, and this can create a close-knit environment
  • Fast paced
  • Little or no structure so lots of ambiguity and white space
  • Very little red tape
  • Less rules/more flexibility


  • Expect to work… A LOT.  Especially if your company starts to take off
  • Must wear many hats.  There is no, “that doesn’t belong to me.”  Everyone must pitch in
  • Like a small town, everyone talks so privacy can be challenging
  • Little or no structure so lots of ambiguity and white space (included in both pros and cons because it appeals to some and not to others)
  • The lack of structure and policies can make every task take twice as long… because you’re doing both simultaneously
  • Fast paced (pro or con depending on your preference and work style)
  • Low, low budgets.  So, no fancy agencies to help with the workload
  • Base pay tends to be lower
  • It’s almost impossible not to work on vacation because there is likely no overlap in jobs so if there’s an emergency, you’re working under the palm trees
  • There’s always the question of, “when will our funding run out?”  Job security can be iffy between rounds of raising capital
  • HR may be minuscule or non-existent so performance reviews/promotions/pay raises are largely optional

These were some of the pros and cons of working in a smaller company. I was drawn to a small start-up after five years in two massive Fortune 150 companies.  I was craving more autonomy and ownership and less red tape. I wanted to see a more immediate impact from my work and feel less like a COG.  I remember my first day at my start-up being so refreshing.  At my first cross-functional meeting, everyone had a voice, regardless of seniority and people really listened to each other. And it felt like we were on a shared mission with a common set of goals.  It was a fun, laid-back group of employees who were all passionate about serving our consumers.  I met some incredible people on the journey and being a part of a start-up was fascinating and extremely helpful for my development. Working at a startup made me realize that size of a company really does matter.

On the flip side, because the product wasn’t as effective as expected, the company was burning money at an unsustainable rate.  During my two years there, I didn’t get a raise or a bonus (there just wasn’t enough money to fund it) and eventually, even though our marketing group of four people drove remarkable awareness and uptake rates, because the product ended up being faulty, return rates were high and we were losing money.  Marketing eventually got eliminated so the smaller company could return to focusing on Research and Development and I found myself without a job.  But this is just one data point out of many.  If your small company does well, your story can be very different.  But the majority of small businesses don’t make it. But if you take the risk and your company does do well, GAME ON (imagine if you had joined Google or Facebook in their meager beginnings?). Size of a company thus plays a crucial role in your career.

Bottom line: If procedures and rules and red tape and make your skin crawl, or if you don’t like conformity, or if you’re a risk taker, a small or medium sized company is likely a better fit for you.

Medium-Sized Company (>$10M <$500M)


  • If you get in early enough, it can be extremely lucrative if the company is growing
  • Some structure is in place so you’re not inventing the wheel every time.  But there’s still opportunity to influence/alter processes
  • Compared to the small company, there is more money for budgets if you make the right business case
  • There is usually an HR department that supports training and development, performance reviews, raises and promotions.
  • Expect to see a lot of changes to personnel, processes, policies, desk location, etc. as the company grows.  This is a pro if you like change.
  • Lots of opportunities to grow or move around the company


  • High scrutiny to how money is being spent
  • Must spend a lot of time making business cases if you need more budget/headcount, etc.
  • Expect to see a lot of changes to personnel, processes, policies, desk location, etc. as the company grows.  This is a con if you don’t like change (or if the change negatively impacts you)
  • If unrealistic goals are set, it can lead to a hostile environment that can spin out very quickly
  • Unlike smaller company, your direct manager has the most control over your success vs. both the big and small company (see notes)

My biggest aha at the medium company was the person you report to is even more important than at a small or medium sized company. Why? Because, on top of all of the intrinsic needs we hope management will satisfy, at a medium sized company, they also play a big role in how much financial support your team gets.  There is a finite amount of money at a medium sized company and more players competing for the pot. Unlike a small company where there’s a high amount of excitement and lots of aptitude to spend without worrying about profit, medium-sized companies now have to start thinking about how to get in the black.  So, if your boss doesn’t understand the importance of your team or if you don’t have a good relationship, there’s a high probability that you won’t get the funding you need to meet your goals.  And that can lead to stress, frustration, long hours, lots of fingers pointing, etc.

On the flip side, if your boss does understand the importance of your team and you do have a good relationship, you may be able to do a lot of great things at a medium sized company. Here again, size of a company seems to play a very important role.

Things change A LOT at a medium sized company.  During my almost three-year tenure, I had three managers, two titles, one office move, a marketing team that grew from ten to forty, three agency changes, innumerable senior manager layoffs, and a partridge in a pear tree.  The only certainty at a medium sized company is that change is inevitable.  But, because I joined relatively early in their growth, this was, by far, my most lucrative career move to date.  But it was also my most stressful by a long-shot.

Bottom line: Be sure you know who you’ll be reporting to (and their superiors, if applicable) and understand the culture and background of the key players. Research the industry well to get a sense of how likely growth will be. If you pay proper attention to these factors then you can utilize the size of a company in your favor.

Big-Sized Company (>$500M)


  • Can add a lot of credibility to your resume
  • Lots of learning and development opportunities
  • Typically, high budgets so lots of opportunity to experiment and outsource work
  • Reliable and competitive pay, vacation, bonuses, promotion structure, usually good health benefits
  • More people to cover you while you’re on vacation
  • Lots of talented people to reach out to for mentorship and support
  • A great opportunity to build your network
  • Opportunity to specialize
  • Company perks (big-budget parties, company discounts, on-site fitness center, food, etc.) which are usually not available at a smaller company or a medium-sized one.
  • Frequent change


  • Bureaucracy/red tape
  • Politics
  • Limited impact
  • The loudest or most senior person in the room can easily trump all other contributions, no matter how brilliant they may be
  • If publicly traded, increased Wall Street expectations quarterly can be stressful
  • Frequent change (included in both categories depending on the change and your comfort level with variety)
  • Can be easy to get lost in the crowd/hard to stick out
  • Harder to “move the needle”
  • Slow moving
  • You may be a victim to a massive layoff
  • No opportunity to become an overnight millionaire

After reflecting on my two experiences with big companies, (Johnson & Johnson and Eli Lilly), I realized that the stress in my job was largely dependent on how well my business unit was doing.  When we were losing money or market share, things became stressful and people around me became nervous (usually, there is a negative correlation between people becoming nervous and how they treat others).   So, the best thing you can do prior to entering a big company is dig into their financials (this is a big advantage while interviewing at big companies vs. small- if they’re publicly traded, you can easily find their financials and trader insights about projected growth).  If the target company is growing and managing a cash cow, has no or limited competition, has created high barriers to entry, and is targeting a growing niche, it can be a wonderful and financially dependable opportunity.

It’s also really hard to be bird of a different color in a large company.  About seven years into my career, I learned that my value of authenticity and diversity of thinking was difficult to honor in a large company so this isn’t an environment that fits me.

Bottom line: You won’t have the opportunity to make millions like you would at the small or medium-sized company but you can make a very good living, particularly if you stay on for a longer period of time.  This is, by far, the best option for those who are extremely risk adverse.

There are common differences between all three options.  Research which one is best for you and choose the right fit, based on your personal preferences.  Putting in the time and energy to research and do some intrinsic work to uncover your priorities will pay off in spades down the road.

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About The Author

Leadership Consultant and Coach Amy Sanchez

Amy Sanchez is a certified executive and career coach located in the Bay Area who specializes in helping mid- to senior-level executives achieve their full potential and build the lives they want.

She has an MBA from USC’s Marshall School of Business and 13 years of corporate experience.

She is a skilled coach and neutral partner who provides clients with tangible tools and effective guidance to successfully navigate the waters of this fast-paced, hyper-connected, high-stakes job market.

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