Navigating Career Paths: My Journey in Startups vs. Corporate Companies

Good morning. I vividly remember the day I had to drive up Sand Hill Road, Silicon Valley’s investor mile—the place to be for venture capital investors. I had the honor of pitching the early-stage prototype of our next product generation.

We had been hustling for months, working long nights from our humble office space or our CEOs' or engineers’ living rooms on weekends to find every last issue before sharing it with the world.

This pitch could mean the difference between ongoing support from our investors or raising concerns about what we’ve been doing—it's high stakes and, we worked on it until the last minute to get a clean build.

While waiting for my turn, with a high heart rate and dry mouth, I couldn’t help but remember my days in my first job in a corporate environment. Back then, I had weeks to prepare a presentation, we had research labs to back our assumptions, and we had a well-established brand and good reputation. What a contrast…

These two scenarios showcase the stark differences between a startup and a mature corporate environment. Each has its unique set of challenges and benefits. I’ve lived through both. In today’s post, I want to share my experiences and how I would start and progress in my career, knowing how I did it in the past.

5-minute-read

Personal Journey

Early Career Choices

I started my career in a very structured environment. Right out of university, I started working for an Early—and Mid-stage Venture capital and Private Equity firm in Germany. I liked the clear career path and the projected stability. I also respected the people I would work with and knew I could learn from them.

My desire for the startup world

However, after a few years of working with this company, I was drawn to the startups we invested in. I admired how our founders crafted their visions and got to work toward them, making an impact with every small task they accomplished.

The rate of change was exhilarating, and I had to be part of that world.

I moved to Silicon Valley for an internship. One early memorable experience was being asked to prototype several possible landing pages for our upcoming app early on. I wasn’t a designer. I had done some web design before, but how could I be the right person for this job? Maybe I wasn’t at first, but it needed to get done, and nobody else had time to do it. It was trial by fire, spending every last minute learning and improving my ideas and learning by doing. It required me to understand and believe in the vision for the product and do whatever it takes to get it on “prototype paper”. I loved it.

Transition back to corporate

After a few years, our startup was acquired by Yahoo, and I entered the corporate world again. The transition was smoother than I thought, and suddenly, I was working on large-scale products with global reach. The mobile app industry was still in its early phase, and many things we learned in our startup applied to Yahoo’s mobile apps and their evolution. This added a new layer of complexity, dealing with millions of daily active users, new management layers, and corporate stakeholders. However, we could apply the early learnings from the many experiments we had run at the startup.

And so it continued

After 2.5 years at Yahoo, the startup bug got me again. I wanted rapid decision-making, fast and scrappy testing of our assumptions, and growth in an emerging technology. I’ve been back in “startup land” for the last 7 years. The last 4 years have been a stage of hyper-growth, which adds another layer to complexity.

All of these environments taught me invaluable lessons from which I can draw. What’s the path you would choose? Is it the firm belief in startups' vision, room for fast growth and lots of experiments on the one hand or navigating corporate environments with clear career ladders, structured processes, and access to a wide range of resources on the other?

I am thankful I got to see both worlds. It gave me new perspectives and new ways of seeing things.

It’s like traveling the world, seeing new things, learning new things, and opening up new perspectives. Why could a career not be the same experience?

Work environment and culture

Life in a startup

Life in a startup is fast-paced, a rollercoaster ride, and constantly changing. Your role could shift daily. In one of the startups I was in, we gave up on roles and called our team the “Whatever it takes team.”

You will build close relationships and notice how crucial everyone’s contribution is.

Pros:

• High level of autonomy, make your ideas happen

• Fast decision making

• Many opportunities ready to take on

• Clear and direct impact on the business

Cons:

• High level of uncertainty

• Lots of change

• Don’t look for established processes

• Resource constraints

Life in a corporate company

Until last year, I would have said it’s a stable environment. But even in established tech corporates, we see large waves of layoffs. So, I think the argument for stability does not apply to everyone anymore; however, there is a larger sense of predictability.

You will find a clear set of hierarchies and established processes and a guide to help you with any operation that needs to be done.

Pros:

• Established career ladder

• Less resource-constrained

• Clear 9-5

• The process will guide you in your work

Cons:

• Every task has a documented process

  • (I know I have it as pro and con, it depends on you)

• Less chance for new opportunities

• Business impact is not consistently directly measurable

• Decisions take longer

The skills gained and the career growth

Skills in Startups

Working in a startup made me very versatile. As these roles overlapped, I developed skills across product management, design, marketing, and engineering. My horizontal role helped me develop an entrepreneurial mindset and shaped my business acumen. I pitched to customers, investors, and users almost daily, which helped me quickly tune my pitch to their reactions.

Skills in Corporates

I learned quickly how to leverage other teams that were specialists in their areas. The luxury of having your own user research team and UX lab, as well as an expert marketing team, helped me hone the deeper skills required for a great Product Manager. I met people who were experts in their craft and found great mentors in different disciplines.

Growth in Startups

Startups are engineered for growth. If the startup grows, so will your career. As you complete projects that help evolve the company, you will expand your role as the product gets built out further. If you ever think of starting your own thing, experience in a small startup is incredibly helpful.

Bonus: If you strongly believe in a future technology and you can find an opportunity in a startup to work on it, it will pay dividends to get this head-start in the industry, and it might open higher-level doors in larger companies later on.

Growth in Corporates

Growth in corporates is well structured. There will be role descriptions, requirements, and milestones to achieve to grow into your next role. Role and even career changes can happen in the same company, as internal transfers to new roles or locations are sometimes an option.

The people you will meet

I want to point out the types of people you will work with. Different types of people thrive in different environments. In startups, you will find very purpose-driven go-getters. They come in, see what needs to get done, and get it done.

If you are a problem solver and want autonomy in tackling problems, startups are a good place for you. No structures exist, and you are expected to figure things out.

The bonds with the people in startups are stronger. You spend long hours with them, trying to overcome hard challenges. But you also celebrate early successes together as a team.

The corporate world is looking for people who can operate in a large machine with many dependencies, stakeholders, and established processes, without disrupting the normal. You will meet experts in their fields that can become great mentors.

Personal Reflection and Tips

If I had to restart my career again, I would now know to plan it exactly like this. I didn’t plan it that way the first time, but looking back, I find the different experiences enriching.

I would do it early in my career when mistakes can easily be fixed, and I can find an environment in which I can thrive.

Knowing the pros and cons helped me determine what I enjoy, what can be transferred, and what can’t or shouldn’t.

I cringe when large corporations promote their company as “we are like a startup.” It feels like saying, “My grandma is just like a big teenager,” or “Our board meetings are like an improv class.” You want it to be, but it just isn’t.

Personal preference

I enjoy making my career an adventure that includes uncertainty, change, and many opportunities to capture. Startups are a great place for that. But to sharpen your skills, find great mentors, put a big brand on your resume and learn about structure, a corporate environment in the mix can further help you grow.

Looking back, I am glad I got to see both worlds. Only when you have experienced both will you know the right path for you.

This was a bit more of a personal reflection. I hope you enjoyed this and found value. I would love to know from you what else would be interesting, you can let me know with just one click below.

Have a great rest of the week.

Best,