Advice from Harley Finkelstein, COO of Shopify

In episode three of the Second in Command Podcast Cameron sat down with Harley Finkelstein, COO of Shopify.

Harley’s Background

Harley Finkelstein is a Canadian businessman, entrepreneur, and public speaker. He’s also best known as the Chief Operating Officer for Shopify. He’s on the board of the C100 and an advisor to both OMERS Ventures and Felicis Ventures. He’s also a new dragon on CBC’s Dragon’s Den, which is the Canadian version of Shark Tank. He received his bachelor’s degree in economics from Concordia University. He then attended the University of Ottawa where he founded the Law MBA Society and also the Canadian MBA Oath while working towards his law degree and his MBA. After completing both his law degree and his MBA, Harley worked at a law firm in Toronto for a year.

How Shopify found their new COO

In 2008, when Harley moved to Ottawa, he was searching for some entrepreneur hang out spots and was directed to a coffee shop in the Glebe (a really nice area in Ottawa). It was here that he first met Tobias, a brilliant entrepreneur who was transitioning out of selling snowboards online to creating this software company. He wrote this piece of software to sell the snowboards online and quickly realized how his platform could be turned around to help other entrepreneurs all over the world. At the time, Harley was preparing to be called to the bar and eventually moved to Toronto where he would work for 10 months as a lawyer.

In 2009, Tobias, CEO of Shopify, spoke with Harley and they began talking about opportunities for the company. Harley was an early merchant and customer for Shopify and it was in 2009 when he moved to Ottawa with his girlfriend (now wife and mother of his child) to start working as a “Swiss Army Knife” for Shopify. Essentially, finding tasks that others did not want to do or did not know how to do and making sure the amazing product they built continues to be properly commercialized.

The COO/CEO Relationship

As COO, Harley recognizes that Toby is his boss. However, he is much more than that. He is also a mentor, and one of Harley’s closest friends. They spend a lot of time together and their relationship extends well beyond just the office. In terms of making sure the dynamic is as effective as possible, the onus falls on Harley. As the COO, Harley feels it is his responsibility to check in with the CEO and make sure that he is getting everything that he needs. A lot of the problems that the CEO/COO relationships often stem from either are misalignment,in terms of expectation or the data, or the prospect that they’re working through is actually dated and things have actually changed.

Harley’s advice to other COO’s

Finding a balance between work and home life is the key. Harley typically will visit the gym for an hour after work before he goes home to his wife and daughter. This clears his head and allows him to go home with a clear mind. From day one Tony and Harley agreed that being home for dinner and weekends with their wives, and now children, was a major priority. Even during the IPO roadshow, they were making it to 93 meetings all over the world and still home for those Saturday’s with the family.

Finding passions outside of work are truly necessary to be fully focused when it comes to Monday back at the office. During the summer he needs that quality cottage lifetime, and in the winter he needs to hit the hills with his skis.

This might be common sense and pretty obvious, but if there are more than five or six people in a meeting, it’s not a meeting. It’s a presentation, and there’s no way to have a great discussion with that many people. When conducting meetings it is important to consider that most people regard the meeting as ‘doing the work’, Harley does not believe that. The meeting is a good way to set the context and help get the work done in a more efficient or effective manner, but having a meeting should not be a checkbox next to a to-do list. That is ineffective. The onus is on every single person in every single meeting to say, “Is this really a meeting that should be happening? Are the right people in the room? Is there a clear objective?”.

Shifting the mindset away from treating meetings as “work”, and making an effort to create a rich work/life balance are the key takeaways that Harley leaves us with.

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