Why I Left the 'Coolest Job in America' for a Startup

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Senior Director of Marketing Communications at SAP
4 min read
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A year ago this week, after close to eight years, I left Microsoft and jumped headfirst into the world of startups and joined Porch.com, a home-improvement network.

I was very fortunate to have built my career at Microsoft. From Windows to Xbox and places in between, every day I was given tremendous opportunities to grow and was supported with all the resources anyone could ever ask for.

Many people would consider my last position at Microsoft a dream job. I served as director of sports marketing and was responsible for carrying out marketing activation and execution of Microsoft’s partnership with the NFL. My friends called it the “coolest job in America.”

Related: Are You Cut Out to Work at a Startup?

In addition to being well compensated I literally spent my days walking, talking and breathing football. As a lifelong fan of the New England Patriots I had a job that perfectly blended my personal interests with work. Simply put, I had a job that in many ways never felt like a job.

As fun and cool as the job was I couldn’t ignore a very real emotion: I had an entrepreneurial itch I needed to scratch.

But could I handle the risk? I was in a role that I loved that was paved with clarity. Did I have what it takes to walk the unproven path and succeed?

As I look back on the last 365 days I can say with a high degree of confidence that the risk and move from corporate life to startup world was the 100 percent right thing for me to do.

For anyone considering a move from the big company environment to chase his or her entrepreneurial dreams, here are a few things you will learn and experience at a startup.

At a startup, every moment counts.

When you work at a big company things move slower. Even the best ideas require internal reviews with stakeholders before moving ahead.

Here’s what I can tell about startup life. 
Every moment counts. Every day, hour and minute is material to the success of the business. You don’t have time to waste in frivolous meetings. There is no time for piles of emails where stakeholders weigh in with their two cents. If you are at a startup with a really great culture you there to do your job, do it well and do it fast.

At a startup, you find out how good you really are.

To be completely honest this is the number-one reason why I had to leave Microsoft for a startup. Was I really good at what I do or was I successful because of the resources at my disposal? Could I still do the basics -- the fundamentals of my discipline -- if I had nothing to rely on behind my own skills and the corresponding talents of my teammates?

Here is what I can tell you about startup life.
You will find out very fast if you are as good as you think you are. As mentioned in my first point you don’t have time to waste. You need to show conviction in your instincts. You need to rely on your superpowers. You can’t hide behind others, agencies or huge budgets. Success comes down to one element: you. If you perform the results shine through immediately. If you cannot, those mistakes are amplified and made clear instantly. You find out very fast how good your best really is.

Related: 9 Reasons to Quit Your Job As Soon As You Can

At a startup, it truly is all about the people.

Culture is everything at a small company. As a leader, you have the opportunity to develop teams and people that fit within the values, principles and characteristics that matter most to you. It’s not about having pockets of great culture, its about having a great culture that permeates through every level of the business.

Here is what I can tell you about startup life.
Nobody ever achieved anything without the support of a great team. The business thrives when they thrive. For a startup to be successful everyone needs to be 100 percent all in. When you have the right mix of people, amazing things happen. There is no room for bad apples as the culture of the business trumps everything else.

When are you in the trenches with a team that is completely bought into the vision and everyone is executing at an exceptionally high level, you will experience some of your greatest career fulfillments. 

Related: The Most Important Career Choice You'll Ever Make

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