Lessons in Career Disruption—5 Tips for Moving From a Corporate Job to a Startup

By Keith Crerar

Everyone remembers the first day at a new job. Mine was in March 2015. After spending close to a decade working for a publicly traded company, at age 40 I decided to move to a startup at age 40—about the same time other guys are locked in midlife crisis and buying motorcycles.

Having been well-entrenched in buttoned-up corporate culture, I arrived for my first day at TradeRev’s Toronto headquarters in my best dress shirt, a nice tie, and a fitted suit . . . and I’ll never forget what happened next. As soon as I walked through the doors, a young web developer in a t-shirt and jeans asked me if I was someone’s father. (Needless to say, not the greeting I was expecting!)

In the past two years, I have since learned many more differences between corporate and startup life. So, in hopes of helping others avoid the culture shock that comes with career upheaval, here are five things that anyone transitioning from a corporate environment to a startup should bear in mind:

1. You have to believe in what you do

To survive at a startup, you have to hustle. There will be many late nights, working weekends, and personal sacrifices you’ll have to prepare your family for. That’s why, before joining any new company, you must be absolutely certain you believe in your founder’s vision.

In my current role, I really believe in what I do, helping bring real-time car auction technology to dealers’ mobile phones. You’ll also need to bring that same passion to your new position. If you don’t, you’ll never hustle hard enough. You just won’t.

2. You must be ready to embrace chaos

Ask yourself, how do you perform under pressure? Because, make no mistake, things are going to go sideways at a startup and you’ll need to stay flexible and keep an open mind in the face of chaos. When you’re building something new and disrupting an entire industry, you’re going to have some hiccups. There will be bugs and all kinds of unforeseen setbacks, but if you can keep your cool as a leader, you can help your team stay calm.

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3. You have to be willing to learn

I went from heading up a team of 800 to managing a team of 50, and am now more hands-on than ever before. At a startup, you don’t direct the troops, you are the troops. And, to thrive in this life, you have to be able to move outside your comfort zone and take on new, unfamiliar roles on a daily basis.

At my old job, the sales team that spoke with customers was far removed from the product development team. But, now I’m in those development meetings. I’m learning about coding and product roadmaps, working with engineers, and I am part of big decisions to adding new features to our mobile app. It’s exciting.

4. You need to keep your ear to the ground

When you’re at a large organization, leadership can quickly become disconnected from the people who are directly talking to the customers. However, when you’re small, you have the chance to connect with employees and customers on the ground floor—and you need to capitalize on those opportunities every chance you get.

The objective of every startup is to grow its customer base; growth only comes with great customer service, so your boots need to be on the ground. You have to put yourself in position to hear unfiltered customer feedback firsthand.

5. You will have the opportunity to shape company culture

Coming from a structured corporate environment I had to learn that nothing ever has to be a certain way. As long as everyone is working together towards a common goal, it doesn’t matter how you look, how you dress, or who you are. All that matters is the job gets done, you have fun, and you take care of each other.

While the culture at most corporate work spaces is largely set in stone, at my company, I have a real opportunity to shape how our employees work and play. This means taking the time to say good morning to everyone, blaring my iTunes through the office to motivate the team for an upcoming launch, and helping present custom-made, company-branded Chuck Taylors to employees on their one-year anniversaries.

These are the things that make the long hours worth it. Over the past two years, I’ve learned that if you can create a workplace that people enjoy being a part of and get satisfaction from, coming to work each day becomes much more than picking up a paycheck.

While corporate life may have been more comfortable, I wouldn’t trade my experience at a startup for the world. I mean, having the chance to disrupt an entire industry? That’s definitely something worth disrupting your life for.

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