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


Startup concept

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.

RELATED: Are You Suited to Working at a Startup Business?

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.



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