Harley Finkelstein: From Class President to the President of Shopify

A lawyer by trade, Harley Finkelstein met Tobi, the Founder of Shopify when he began his entrepreneurial journey, selling t-shirts through Shopify. Shortly thereafter Harley realized that the way to pursue his passion for entrepreneurship was to join Tobi on his mission to make entrepreneurship accessible to everyone. Today, Harley is the President of Shopify.

Listen to this episode (or read the transcript below) to learn how Shopify hires and retains the best employees.

1 You were class president in high school, right?

I went to a very large, typical US public high school with around four thousand kids. I was a short Jewish kid; I couldn’t play basketball or play football and I realized that a lot of people in high school found their identity through their extracurriculars. Whether it was sports, drama, or debate, I was drawn to student politics. I liked the idea of advocating for people that may have otherwise not been able to advocate for themselves and I liked the idea of leveling the playing field in a way that was effective and valuable for others, which may have even led to my passion for entrepreneurship. I’m assertive, aggressive, and incredibly extroverted. Tim Ferriss refers to me as a power expert, which I think is accurate.

2 Can you be an entrepreneur without simultaneously being a leader?

At Shopify, we talk a lot about this idea that we are leaders, and we want all of our leaders at Shopify to think about doubling down on their strengths as opposed to mitigating their weaknesses. Shopify is currently from a market cap perspective, the largest company in Canada, we’re one of the largest companies in the tech industry in the world and one of the things about most big companies is that they tend to want their leaders to be these well-rounded objects and know about everything. At Shopify, we’ve taken a different approach. If you’re really good at this one thing, we want you to become the best in the world at that one thing, and we will help you bring on people to fill those weaknesses.

One thing that I’ve embraced in the last six or seven years is realizing that Shopify is not my only life’s work, but I also recognize that Shopify may be the greatest place in the world for me to grow, learn and develop.  I like to say that every single year I work at Shopify, it feels like I’m getting 10 years’ worth of career development, which is amazing. The prerequisite to that is that I have to show vulnerability. I need to hire people that are better, smarter, and faster than me and I need to listen to them.

3 Have you ever had a real manager or someone that you reported to outside of Tobi at Shopify?

I guess the only sort of job I’d ever had other than Shopify was as a lawyer. I worked in a law firm in midtown Toronto, and it was a corporate finance firm.  I had senior lawyers supervise me and they were terrible managers and leaders. They were uninspiring, they didn’t teach at all. It’s fairly common in a lot of service-based professions, particularly in places like law firms, where the unit of productivity is time-based so the more hours I work, the more they can bill clients, which is good for the firm and increases their profitability of the year. But there was no interest or no appetite, to teach me how to do things better and more effectively and it pushed me to entrepreneurship. And in fact, it pushed me to call Tobi and say, I was one of the first merchants on Shopify, I know what Shopify did for me, I want to offer that to others and the end result was leaving as fast as I could and moving to Ottawa to work for Tobi.

4 How do you hire with your long-term vision in mind?

How do you hire people that are effectively unhireable? You extend the process of engagement, you extend the dating process, that’s how you hire people that are effectively unhireable. People that are ‘unhireable’, are usually also very, very well paid so a financial incentive isn’t always going to be the trick to get them to come over, but you are showing this very long-term, multi-year interest in them. It’s not a sure thing but it may be the difference of someone feeling like the company really wants them to come work with them.

5 How do you retain employees for so long?

Lindsay Craig, who leads brand at Shopify, wrote this great blog post about this idea of the career path not being a ladder, but being more like snakes and ladders or as she refers to it as a jungle gym and that’s a big part of the culture at Shopify. Shopify is a place where your path inside of Shopify, whether it’s five years or 50 years, may not look like a traditional path. We have people that have led teams of 50 or 100 or 500 people who decide at some point they just want to be an individual contributor, and that’s okay. Or we may have someone who is an amazing salesperson who decides they want to learn how to code and go be a junior developer or an apprentice Product Manager. At Shopify, it’s okay to look at your career like a jungle gym, as opposed to a ladder that has to go up.

The second thing that helps us with retention is our ability to continuously evolve. As someone that works at Shopify, whether it’s for a long period or a short period, we don’t want you jumping around too much because you know, you need to get deep in something before you have the conversation to go to something new but there are enough opportunities that all these different teams at Shopify feel like they can have multiple careers at the same company. Not only do we make that available, but we also encourage it and we think it’s a really neat thing.

6 When did you really start to understand how impactful culture is within a company?

I’m reminded of it almost daily. When COVID started the Irish Prime Minister had a really great speech that said, “Let the world say about us when things were at their worst, we were at our best”. The way that Shopify showed up during the COVID-19 pandemic, to not only support existing entrepreneurs and existing small businesses but also to invite more people to supplement their income to or replace their income or even to adapt and pivot their business showed the world who we are. I think a big part of the reason why we were able to step up and adapt was because of our culture which thrives on change.

7 Do you have any tips, resources, or words of advice for leaders or managers that are looking to get better at their craft?

The best thing that I’ve done for myself to improve my management skills or leadership qualities is continuing to find really great people that I admire, and I learn from them. I’ve had the chance to meet some amazing managers and leaders from all around the world and I essentially just ask them how they do it so I would recommend that everyone keeps a list of people that inspire them or people they look up to.

Stephen Beckta is one of the greatest managers in the world, he’s a close friend of mine and he runs three of the best restaurants in Canada and the way he gets his staff to care so intently is brilliant. Stephen is in the culinary industry and I’m in the tech industry but there is still so much I can learn from him. When you begin to create a list of managers or leaders that you want to emulate, you can start to ask them questions and learn from them. Creating a set list of mentors, and people that you really admire when it comes to managers and leaders has been very effective for me.