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Early in my career, I walked into a shared office space on my first day as a full-time software developer and sat between the CTO and CEO for check-in. The four of us were complete. Before that day was over, I got my first assignment.
This was one of the most formative—and most stressful—things in my professional life. In the ten years since then, I’ve worked at a dozen companies that include Fortune 100 firms, mid-sized startups, and companies you’ve probably never heard of. I also spoke with nearly a thousand developers at various stages of their careers.
Many developers entering the field are obsessed with getting to Google, Meta, or Amazon. But those roles represent about 0.6 percent of software engineering positions. For most of us, the real choice is between a small startup, a mid-sized company, and a large corporation. Each comes with tradeoffs, and your experience will differ from mine. What follows is an honest account of what you might reasonably expect.
Starting Small
Benefits
Your work is actually important. The feature you’re building can determine whether a company closes its next funding round. You get exposure to the full spectrum of business, from shipping pipelines to sales and operations and everything in between. He wears many hats out of necessity. For developers who want to grow quickly and understand how the product is ultimately built, there are a few fast-moving areas.
Evil
Everything is on fire, always. Work-life balance is hard to maintain when every release feels critical. Priorities change without warning and culture tends to reflect the personality of whoever has the most influence in a small room. Startups prioritize speed over craft which means engineers learn to move fast but don’t always learn to build well, and that gap can follow you into your next role.
Middle Company
Benefits
“So this is how real business works.” There is process, documentation, quality assurance work, and some sort of work structure. The team is large enough to offer diverse experience and perspective. Stability is a myth, especially these days, but it is much more visible than the first phase.
Evil
“So this is how real business works?” Quality-enabling processes also produce conflict. Access controls, approval workflows, and cross-party dependencies make things slow. The career ladder is there but can stop at senior engineer. Without significant organizational growth, your salary and title may increase early.
Big Business
Benefits
That badge on your LinkedIn profile just bought you credibility for the next five years. Compensation at this level can be reasonably high, especially if equity is included. The career ladder is long and clearly defined. Engineering processes in mature organizations tend to be strong, and a recognized employer carries market value in future job searches.
Evil
It’s slow going. Technology stacks often lag industry trends by several years. Political power shapes development as much as technical ability does. Skill atrophy is dangerous if you spend years on a small piece of legacy system. You are now a small fish in a big pond and it will be hard to get attention.
The Roadmap I Will Take If I Had To Start Over
According to a recent Stack Overflow survey, 47 percent of professional developers work at companies with fewer than 100 employees. This may surprise you because social media is full of developers who work for the most famous companies in the world.
The way most developers think about themselves and the way most developers walk are two very different things.
If I could do it all over again, here’s the approach I would take: Start at a small company to build scope and learn how the business works across functions. This also provides room for experimentation within different roles. Next, move to a medium-sized organization with a clear goal of reaching a senior or leadership role. Making a lateral move is easier than trying to move up at the next company. Finally, target a mature company where a leadership position opens the door to meaningful equity and long-term growth (stocks and bonuses).
Each stop creates something that the others cannot. Getting started gives you scope. A mid-sized company gives you a taste of how large orgs work. Business gives you power, credibility and maybe some stability.
Your path will not look like mine. At the start of five people, I didn’t know what I was getting myself into. In retrospect, I wouldn’t trade. Just know what you’re signing up for before you sign.
—Brian
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