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'My profs became an informal board of directors'

Now CPO at Shopify, Harley Finkelstein graduated from student entrepreneur to business guru
January 15, 2014
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By Alyssa Tremblay


Cancel that plane ticket to Silicon Valley, because one of the world’s most successful Internet start-ups is within walking distance of Parliament Hill.

Ottawa-based Shopify.ca provides software and resources to help businesses build online stores to sell their wares. The company is currently valued at $1 billion, making it the first Internet startup in the country to reach such heights since the dot-com bubble burst in the early 2000s.

Harley Finkelstein Harley Finkelstein, BA 05, chief platform officer at Shopify | Photo courtesy: Harley Finkelstein

But landing a job with Shopify is no walk in the park — in fact, for some it involved literally trekking through woods.

“While I was camping in Utah, someone actually found me there just based on my Instagram location and delivered a job application to my tent,” said Concordia alumnus Harley Finkelstein, Shopify’s chief platform officer.  

Finkelstein was behind an unusual job posting that eschewed the traditional interview process and asked hopeful applicants to “hustle their way in.”

One applicant showed up at Shopify’s offices with his resume attached to a skateboard. Another sent Finkelstein a series of singing telegrams, each a part of a riddle that ended with the job application. In total, over 500 people applied from around the world.

The goal, Finkelstein explains, was to get candidates to prove they could do the job before they were even hired.

"Given that the role is for business development, which is all about creativity, I thought that the way to get the job should be similar to what the successful candidate would have to do if they got the job," he says.

Finkelstein, BA (economics) 05, is a testament to the tough love that he preaches. Financial difficulties prompted him to start a screen-printing business to support himself while studying as an undergraduate at McGill.

While the T-shirts paid his tuition, he switched to Concordia for the final two years of his degree because its curriculum and scheduling were more accommodating to a student-entrepreneur like himself. He graduated with distinction while growing his business.

"Concordia was not only willing to help me but they wanted to help me," Finkelstein says. "Even the faculty was very supportive. Whether we were talking about profit margins or marketing, I was able to create my own sort of informal board of directors out of my professors."

Being able to incubate ideas in the classroom and then enact them in his business was a big advantage to Finkelstein.

"If you can balance academia with entrepreneurship, you actually have an incredible formula for success because then you can learn about stuff in the classroom and try it out in your business,” he says. “You also have this incredible fall-back plan — if everything failed, at least I was still in school.”

But Finkelstein’s screen-printing business — unlike his menagerie of past ventures selling slippers, watch winders and poker chips for fraternities — didn’t fail. Instead, in a decision to sell his T-shirts online, he became one of Shopify’s first customers and was eventually hired by its CEO Tobias Lütke. Today the 350-person company boasts 85,000 e-commerces stores in over 100 countries.

As Shopify’s chief platform officer, Finkelstein leads business development and sales. As he explains in a Fast Company magazine article, he's responsible for the creation and development of relationships with value-adding partners, ranging from app developers to theme designers and anyone in between. 

"Shopify is this really incredible high-speed train. It helps small businesses move their businesses online. But in order to get on and off the train, like at a train station, you need a platform. That's kind of what my role is — I help merchants come on to Shopify," he explains.

Between Shopify hitting the $1-billion benchmark and raising over $100 million in venture capital, 2013 was a great year for Finkelstein, who’s made a strong name for himself on the side as a business conference and event speaker. The Ottawa Business Journal named him their Newsmaker of the Year and Ottawa Citizen Style Magazine called him a person to watch in 2014.

As for new year’s resolutions, Finkelstein’s personal goal for 2014 is to be more vulnerable, challenging himself to step into unknown territory by taking pottery courses and guitar lessons.

“I want to get really, really comfortable with being uncomfortable," he explains. "I believe that the magic happens when you step outside your comfort zone."

As for work, this year is all about building up his team at Shopify.

"I want to shift the focus from my own growth to my team's growth," he says. "In the past, as an entrepreneur, it was a one-man show. Now I want to be the best leader I can be."



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