What Size Company Is Right for You? Here’s What I’ve Learned Going From Startups to a Fortune 500 Company

What Size Company Is Right for You? Here’s What I’ve Learned Going From Startups to a Fortune 500 Company was originally published on The Muse, a great place to research companies and careers. Click here to search for great jobs and companies near you.

Last year, after a decade of working at small startups, I set my sights on larger, established companies: Series Bs, recent IPOs, and the Fortune 500. Recently married, in my mid-30s, and staring down a global pandemic, I was looking for stability and structure, two things not typically associated with small or early-stage companies.

Big companies weren’t entirely new territory for me; I started my career at Caterpillar and I interned at Time Inc. while I was still in school. But it’s definitely been an adjustment going from a struggling startup with 20 employees working out of a converted loft apartment to a multinational corporation with enough employees to fill a large city.

I’m glad that I’ve found a place where my contributions matter and I’ve got room to grow. But if you’re thinking of joining a large team, it’s fair to question whether the grass is really greener on the other side. Aren’t big companies slow and old fashioned? Will you be stuck working alongside a Dwight Schrute?

Frankly, it’s not black and white. It depends on what kind of environment you thrive in and what your current priorities are. I’ll share the most significant adjustments I’ve noticed as I transitioned back to a big company and what the advantages and disadvantages have been for each one. But remember—what seems like a pro to me may be a deal breaker for you, and vice versa.

And of course, every company is unique, so while some things are more likely to be true at larger or smaller companies, it’s always worth doing specific research on a company you’re interested in to see if these general trends apply.

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Adjustment 1:


Just how big is a big company? Within the Fortune 500, a group of America’s largest companies (based on revenue), the average headcount is about 60,000. But the number of employees ranges from about a thousand to a couple million. At The Muse, we consider any company with more than 500 employees to be a large company, but keep in mind that there’s a pretty wide range of employee headcounts within that category.

Big companies don’t have to be publicly traded. Some of the largest firms in America, like PricewaterhouseCoopers, Publix, and Hearst are privately owned. Many late-stage VC-backed startups including Stripe, Robinhood, and Warby Parker have thousands of employees too.

Read More: These Fortune 1000 Companies Are Hiring Right Now


  • You can count on formal processes and support. Large companies have a full-time human resources staff whose job it is to support hiring, onboarding, benefits, conflict resolution, complaints, and career reviews. Need help determining what your health insurance actually covers? HR can give you a definitive answer.
  • Expertise is a phone call away. As headcount grows, so does specialization. When I worked at Caterpillar, there was an engineer who was the subject matter expert on nuts and bolts. In another building, there was a team of machinists who could prototype practically anything. In my current role, we have teams dedicated to supporting individual systems. If something critical crashes, I know someone accountable and knowledgeable is available to respond. This is a departure from the “deal with it” mindset of smaller companies, where it’s common to wear multiple hats and take ownership of problems. At a large company, you’ll have a narrowly defined set of responsibilities and an escalation path when things are tough or unclear.


  • Large companies tend to offer less flexibility. Policies on salaries, corporate expenses, raises, vacation, and remote work are likely to be set at the company or division level. If your company is based in Chicago, but you’re in California, your compensation package may be representative of their local options and market rates, not yours. Some of this is related to fairness and saving money: Offer everyone the same thing and nobody can cry foul.
  • Big organizations suffer from a lack of shared context. With multiple offices, product lines, or functional areas, as well as cultural and language barriers, keeping everyone on the same page is quite difficult. Every time I reach out to another team or department, I have to explain what team I’m on, what my product does, how it affects them, and why I need their help.

Adjustment 2:


Whether a big company is 150+ years old (Colgate-Palmolive, JPMorgan Chase, Macy’s) or relatively new (TikTok, Tesla, Zoom), it doesn’t happen overnight. These organizations snowball, accumulating employees, offices, technology, processes, expertise, market share, and momentum.

Depending on your point of view, momentum can be safe and supportive or bureaucratic and restrictive.


  • Stable revenue helps big companies ride out tough times. Large companies have entrenched cash cows that generate a lot of revenue. Google’s advertising revenue came to about $135 billion in 2019, for instance, and Procter & Gamble made $71 billion selling Tide, Charmin, and its portfolio of home and personal care goods in 2020. Unlike a startup with a limited runway or a small company with inconsistent cash flows, large companies don’t have to worry as much about running out of funding, collecting on accounts receivable, or pivoting their business model due to a bad quarter.
  • Large companies can afford to invest in “moonshots,” research and development (R&D), and new initiatives. Case in point, it costs pharmaceutical companies $2.6 billion to develop a new drug and bring it to market ($2.9 billion if you include post-approval R&D). But big companies can afford to do it and won’t go broke if it fails.
  • Big, established companies are more likely to have name recognition. This helps at home and in industry. My parents know exactly what Apple and Amazon do. But they couldn’t tell you anything about my professional career from 2010 to 2019. Similarly, if you’re trying to get a meeting or negotiate a deal, a well known and established company name can open a lot of doors—even if they don’t know you.


  • Every big company has a closet full of legacy skeletons. It might be outdated billing systems, mainframes, manual processes, or corporate policies that haven’t been updated in 15 years. Unfortunately, momentum goes hand in hand with inertia. Legacy systems remain in place because they’re critical, they’re expensive to build, and replacement is perceived to be too risky. When a company does get around to overhauling a legacy system, it’s almost always a multiyear effort with significant compromises. It’s difficult to rebuild something when your entire business depends on it. As a result, not everything you work on will be new, revolutionary, or high-tech. And you’ll most likely spend a lot of your time using one of these legacy products or processes—or maybe even keeping it on life support.
  • Inertia can negatively affect employee creativity and innovation. Big companies can be plagued by a “that’s not how we do things here” mindset. Your new idea may be tossed aside just because it represents a different or unproven approach. Not every team and company operates this way, but it can be difficult to tell from the outside. One question you can ask during the interview process is, “Can you give me an example of a time when someone on the team suggested a new idea and how it was implemented?” Otherwise, once you receive an offer, do your research and try to talk to past and present employees.

Adjustment 3:

Career and Compensation

Career progression and compensation look a little different depending on the size of the company along with other factors. Don’t forget that your career is more than your past jobs, titles, and paychecks—it’s the summation of what you’ve learned and achieved. So whatever type of company you work at, you should do it because it helps you grow, not just because it pays the bills.


  • Large companies are a great place to start your career as a new grad. You won’t be the first person to do this job, nor will you be the last. You’ll have access to a wealth of institutional knowledge, training, mentors who have been in your shoes, and structured support to help you succeed. After college, I joined Caterpillar as part of a class of trainees. For the first year, our job was to learn, not to execute. We spent our time in training classes, talking to more experienced engineers, and working on small, but increasingly difficult tasks. In contrast, none of my roles at smaller companies had any structured learning or planned career progression. The exact situation will vary by company, of course, so ask questions before you accept an offer if this kind of structure is important to you.
  • You’re more likely to have a manager who has experience managing and has been in your shoes before. Early on, startups and small companies hire for execution, not management skills. Startups, in particular, prioritize hires who can start contributing immediately, without extensive training or support. Why? Until it reaches profitability, a startup has an expiration date and must conserve capital. In some cases, that means they simply don’t have the time to nurture junior talent.
  • Big companies tend to offer clearer paths to promotion. With a more established company and a large workforce, there are often more structured paths to advancement and more levels to advance through. As you accumulate experience and responsibility, you can move up, and you’ll have a sense of what’s required to get to each level. At Caterpillar, it was always assumed that we’d evolve into fully capable engineers and eventually senior engineers. Fifteen years later, many of my classmates are still at Cat, leading projects as senior managers and technical experts. In small or flat organizations, and especially at startups, promotions are often driven by attrition or other factors outside your control, rather than achievement. In other words, it depends on what the company needs right now, and whether you happen to be in the right place at the right time.
  • The corporate ladder doesn’t just go up, it also goes sideways. Lateral career moves—such as engineering to product, operations to marketing, or finance to strategy)—enable you to apply your skills and experience in a new direction. It can be easier to make a lateral move at a big company because ultimately, all employees are replaceable and your team will have processes to backfill your role. You will be missed, but not so much they won’t let you go. In a smaller organization, you might be “too important to lose,” and unable to fully transition out of your old responsibilities.
  • Your paycheck is more likely to arrive on time and grow steadily. Working at a big company means there’s little chance of late payments and other fluctuations. You’re also much more likely to receive regular cost-of-living raises.
  • Big companies offer extensive benefits beyond healthcare. You’ll likely have access to more insurance options, legal services, purchasing discounts, a pension or 401(k) match, and more.


  • Career advancement also involves more bureaucracy and competition. It can be hard to identify top performers in a large workforce, where the difference between good and great might be a few dollars in sales or lines of code. Sometimes, promotions come down to tenure or something as transactional as getting an advanced degree or certification and you simply can’t get around those requirements. Unfortunately, not everyone is going to make it to the manager or VP level. That’s the nature of corporate hierarchies. A bigger team means there will be more competition for that corner office.
  • Big companies have a clear idea of how much your role is worth. That can be a pro, in the sense that you may not have to argue to earn within market rate. But it also means big companies aren’t likely to budge too much on compensation. Unless you’re an executive, you should expect a modest negotiation range—in my experience, probably not more than 15%.

Adjustment 4:

Work Environment

We’ve come a long way from IBM’s short sleeve shirt and black tie dress code and The Office’s bleak depiction of “regional office” life.


  • For better or worse, startup culture has gone mainstream. Many big companies have begun offering lax dress codes, “unlimited” vacation, standing desks, modern tools (Slack! Gmail! MacBooks!), free snacks, and other classic startup perks.
  • For the tech and software crowd, Agile development has largely replaced the Waterfall model. Say goodbye to coding for two years without ever deploying or getting customer feedback. Big companies are moving toward more iterative, responsive, and design-conscious workflows.
  • At a large company, you can find your community. Many companies with large workforces have the resources to support multiple affinity groups for Black, LBGTQ, Latinx, and other communities as well as folks who have shared interests or hobbies or play certain sports, which means you can find your community within the larger workforce. These groups are usually run by employees and not the company itself.
  • Big companies are friendly, but they are not family. As employees, you and your coworkers have a mandate to work together and deliver value to shareholders and customers. You do not have an obligation to love each other unconditionally, hang out off-hours, or make your identity about work. For me, with a family to go home to now, this is a plus, though I loved Thursday night happy hours and weekend ragers with my coworkers when I was 22.


  • You may have to expand or shift your schedule. Big companies often have multiple offices and distributed teams working across time zones. I work with folks on the West Coast as well as in India. They’re often up early and I often work past 6 PM so we can communicate in a timely manner, instead of waiting a whole day to get a response.
  • Security can get in the way of productivity. RFID (radio-frequency identification) badges, two-factor authentication, and complicated password rules are standard even at small companies. But big companies are a whole other ball game with email phishing tests, internal security teams, and the use of other tactics to maintain security. While well-intentioned, it can be very bureaucratic, especially if you’re coming from a smaller operation.
  • It’s a little flip, but big company, big inbox. I get a lot of email that has no bearing on my job or my team. It’s just corporate updates about new executives, quarterly earnings, and new policy announcements. Personally, I’ve learned quite a bit about email filters in the last few months.

Occasionally I do miss my scrappy startup days, but overall I’ve enjoyed the move back to a bigger company. The incentives and stability align with my career goals and I’m working on challenging problems.

If you want to move really fast and have a high tolerance for risk and uncertainty, a small company or startup might be the right fit for you. On the other hand, if you’re more risk averse, less financially secure, or want more guidance as you start your career, a larger company may support you better.

Whatever your personal and career goals are right now, think about which environment will help you reach them and go into your job search with open eyes and an open mind.