Shopify COO Harley Finkelstein. Photo: Regina Garcia Shopify COO Harley Finkelstein. Photo: Regina Garcia

As a 17-year-old university student, Harley Finkelstein founded a T-shirt business, building a clientele across 50 universities in just three years. While running that business, he became one of Shopify’s first clients. In 2010, he joined the company.

This January, he was promoted from chief platform officer to chief operating officer. The retail software company now boasts more than 200,000 clients and saw the amount of merchandise on its platform double in the most recent quarter compared with a year earlier. Shopify went public on the Toronto and New York stock exchanges in May 2015; its share price has risen by 35% since then.

In this exclusive interview with Canadian Business Editor-in-Chief James Cowan, Finkelstein outlines his company’s vision for digitizing all retail, explains what it takes to scale startup culture, and shares his “weird, dirty secret” for managing better.

Shopify has always put a heavy emphasis on its corporate culture. When you’re hiring during this time of massive growth, how do you ensure people will be a good fit?

Most people assume a great culture is having a cool office or really great perks—and we have those things. But what really defines whether somebody is a fit for your company is how they act when nobody’s watching. What do they do when they are left to their own devices? It’s not about how they act when they know the right answer. It’s about how they act when they don’t know the answer.

That’s a really tough goal. How do you determine someone’s true character through a standard job interview?

You can tease things out. When I’m hiring, I don’t want the guy who played on the tennis team; I want the guy who created the tennis team. I don’t want the guy who participated in some charity; I want someone who created a brand new charity. I look for people who are self-starters—people who have a bit of a founder mentality.

It sounds like you want to hire entrepreneurs.

We try to find the best and brightest. Then we try to remove all the roadblocks and red tape in their way. Most companies of our size have a lot of bottlenecks. This is a company with a startup culture. That means people can run very, very fast. “People can get shit done” is one of our core values. That somehow made it into our filings with the SEC, which is pretty neat.

How does the company change as it gets bigger?

I can’t sit around one table with the entire team and have pizza and talk about the future of the company. That has become more difficult. But we now have four offices. It would be a mistake to impose our Ottawa culture on Montreal or Toronto. That also wouldn’t scale well. So we don’t have one office culture—we’re multicultural. But most things have scaled. Things like town halls actually get richer with the more people you add.

You started with e-commerce, and then dropped the “e” and have started offering a platform that supports traditional retail as well. What’s the relationship between online retail and bricks-and-mortar retail these days?

Most people assume the future of retail is one or the other: It’s online or it’s offline. You have big retailers like Macy’s or Best Buy talking about how online retail is hurting the offline business. Our view is that it’s all digital retail. In the future, consumers will dictate to the retailer how they want to purchase. That’s why our partnerships with platforms like Pinterest and Facebook are so important. We need to empower our merchants to sell on those social networks. But that only serves one customer demographic. In other cases, people still walk into a store, so we have our point-of-sale system. Or they’re buying something at a farmers market, so we need to be able to accept mobile payments.

It’s pretty well-documented that Canadian companies haven’t embraced e-commerce like those in the United States. Why is that?

For a long time, Canadians were buying from American stores where duty and shipping was fairly expensive. That turned off some people. And once consumers weren’t interested, retailers had no reason to be aggressive. But honestly, in the past two years, I think all that has changed. There are some incredible online businesses that started online that are just dominating here in Canada, and we power most of them.

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