Around this time of year, I start getting a lot of questions from my soon-to-be graduates about their next career step. One of the biggest decisions they face is whether to start at a large company or a small-to-medium-sized business (SMB).
I’ve worked for some of the biggest organizations in the world, the United States Army and Apple, as well as for a software startup, Mangan Software Solutions (MSS). I’ve even started my own companies with just a handful of people. There are pros and cons to both, which is exactly why I believe people should experience both at some point in their careers. Each provides different skill sets and learning opportunities that shape you in unique ways.
Large Organizations
My first job out of college was as an officer in the U.S. Army, an organization that has existed for nearly 250 years and employs around 1.3 million people, including active-duty soldiers, reserves, and civilian staff. Today, I work for Apple, which was founded 49 years ago and employs 164,000 full-time employees worldwide.
Why Large Companies Operate Differently
Any organization that has been around for decades, especially large corporations and government entities, has built-in protections to prevent catastrophic failures. These protections typically show up as bureaucracy. SMBs can take risks and pivot quickly, a bad decision might hurt the bottom line or investor equity, but it’s usually manageable. Large organizations don’t have that luxury, a single failure can have massive ripple effects across the economy.
Take the “Magnificent Seven” (Apple, Microsoft, Amazon, Google, Meta, Nvidia, and Tesla). As of 2024, these seven companies accounted for 35% of the S&P 500’s total market cap. Many retirement accounts, pensions, and 401(k)s are tied to these companies. One bad strategic move could trigger economic consequences far beyond their balance sheets and their direct employees. This means risk is managed tightly, sometimes at the expense of speed and innovation.
What You Gain From Working at a Large Company
Exposure to Large-Scale Operations – You see how high-impact decisions are made at scale and gain opportunities to work on global initiatives.
Well-Defined Training & Development – Large companies invest heavily in employee training, mentorship, and career development resources.
Prestige & Name Recognition – Having a well-known company on your resume (similar to a prestigous school) can open doors for future opportunities.
Higher Compensation & Benefits – Large companies typically offer better salaries, bonuses, stock options, and retirement matching. Healthcare, tuition reimbursement, and paid time off (PTO) are also often superior to what SMBs offer.
The Downsides of Starting at a Large Company
Limited Skill Growth & Autonomy – You’re often highly specialized, which means less exposure to different aspects of the business.
Slower Career Progression – Large organizations tend to see you at the level you came in, making promotions harder without job-hopping. This is why today’s workforce changes jobs more frequently than previous generations.
Bureaucracy & Slow Decision-Making – Layers of management can make it difficult to get things done or push through new ideas.
Small & Medium Businesses
Conversely, working for a SMB gives you the opportunity to wear many hats and develop a broader skill set.
When I joined Mangan Software Solutions after leaving the Army, I started as a Project Engineer, then moved to Engineering Manager, then Operations Manager, and eventually became VP of Operations. Over seven years, I touched nearly every part of the business:
Managed developers
Helped with sales pitches & software demos
Worked on marketing campaigns (even making commercials)
Dabbled in coding (until my bad code broke things, lesson learned!)
I gained more exposure and had a direct impact on the company’s success, something that’s much harder to achieve in a large organization.
What You Gain From Working at a SMB
Broad Experience Across Multiple Functions – You’re not just a specialist, you get exposure to operations, sales, marketing, and strategy.
Greater Impact & Visibility – Your work directly affects customers, revenue, and company growth.
More Flexibility & Innovation – You have more freedom to test ideas and see results quickly.
Stronger Company Culture – Small businesses tend to have a more personal, collaborative work environment.
Higher Potential Upside – If your company goes public or is acquired, early employees often receive significant equity rewards. At Nvidia, 76% of employees are now millionaires, with one-third worth over $20M due to stock growth.
The Downsides of Working at a SMB
Higher Risk & Job Instability – SMBs are more vulnerable to market downturns, and job security is less stable than in a large corporation.
More Stress & Firefighting – Smaller teams mean more responsibility, which can lead to higher stress when things go wrong.
Fewer Benefits & Perks – SMBs typically can’t compete with large corporations on salary, retirement benefits, or healthcare.
The Best of Both Worlds
Some large companies have teams that operate like startups, spending years developing new products before commercialization. If you can land a role on one of these specialized teams, you can gain the innovation experience of a startup while benefiting from corporate resources.
Final Thoughts: Which One Is Right for You?
If you’re trying to decide between a large company or a SMB, my advice is:
Take the best opportunity available to you at the time: your first job won’t be your last.
Switch between large and small organizations at different stages of your career to build a well-rounded skill sets.
Stay in a job as long as you’re growing: if you’re stagnant or too comfortable, move on.
Each path offers different advantages. Large companies provide structure, resources, and credibility. SMBs offer agility, ownership, and versatility. The key is to weigh the risks and benefits based on where you are in your career.
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