President of Shopify, Harley Finkelstein.
Stephanie Ricci contributed to this story.
Entrepreneurship has always been a huge part of Harley Finkelstein's life, going back to his family immigrating to Canada, to founding his first company at the age of 17. Today, he is the President of Shopify, one of the world’s leading e-commerce platforms, reducing the barriers to entrepreneurship by helping others start, run, and grow their own business.
Shopify was inspired by a poor online shopping experience. In 2004, three Canadians opened an online store for snowboarding equipment, but the unsatisfactory e-commerce solutions at the time halted their success—so they launched their own two years later.
The all-in-one commerce platform now powers millions of companies of all kinds in 175 countries and represents 23% of the market share in the U.S.
From early customer to president
Finkelstein joined Shopify in 2010 after meeting one of its founders, who remains CEO, Tobias Lütke, at an Ottawa coffee shop. At the time, the company was just transitioning into helping anyone build an online store, and Finkelstein became one of their early customers.
“The experience that I've had as a Shopify merchant, building an amazing company that was competing with the likes of Walmart was so cool,” he recalled. “I would love to help other people have that same experience.”
“It's more about philosophy than size”
For Finkelstein, a key element of the company’s swift success is found in its effort to maintain a flexible and dynamic workspace culture.
"Even though we're a much bigger company with a much larger footprint, we very much culturally act like a startup," he said. “[The culture] should feel as ambitious, as optimistic, as enterprising, as entrepreneurial, as a one-person T-shirt business."
According to him, large companies tend to "lock in" a culture, to which all new employees must acclimatize themselves. That is not the case at Shopify, where every new hire can drive positive impact within the organization.
"Rather than keeping a culture static, make it dynamic, let it be a living tree and evolve," he said. "That is why I can still use the skills I acquired selling T-shirts in college today while running a large, publicly-traded company."
A geo-diverse team
Part of Shopify’s philosophy is the belief that maintaining good working relationships with your colleagues is going to pay dividends no matter how far apart you are.
“The hybrid model often comes off as indecision,” he said. "We're trying to be more decisive to say, ‘work from anywhere, but make sure you and your team are getting together.’”
Since adopting a work-from-anywhere model, even the leadership team can be based in different locations anywhere as long as they have an internet connection. For instance, their general counsel is located in Washington, D.C., while the chief technology officer is in San Francisco and the chief financial officer in New York City.
“This idea of being geographically agnostic has meant that Shopify is a talent pool, and our ability to recruit is so much easier and higher now.”
And yet, some decisions call for the team to be in the same room. The company also launched a concept called “bursting” which brings employees together for team-bonding activities a few times a year.
“Being thoughtful about when it is appropriate to work by yourself, and when you are more productive in a team, has made Shopify a better-run company,” said Finkelstein.
Amid their digital shift, the leadership at Shopify also decided to grow the level of transparency within the organization. For example, the letters sent to the board every quarter are shared with the entire group, while the company enables its employees to voice their concerns or ask questions to executives through anonymous Ask Me Anything forums.
Vulnerability for better leadership
When it comes to his guiding principles for leadership, Finkelstein strongly believes in continuous learning, self-awareness, and a growth-oriented mindset.
“We’re growing so quickly and in so many new directions that for me to remain the president of the company, I need to grow equal or greater to the speed of how fast Shopify is growing,” said Finkelstein. “If you want to lead at a company like Shopify, you simply have to re-qualify for your job every single year.”
While many companies look for leaders to be “well-rounded,” Shopify looks at leadership through an opposite lens.
“We like the idea of having very spiky objects,” said Finkelstein. “If you have a particular skill set, my job is to make that even sharper, and I need to be incredibly self-aware of my weaknesses and hire for my weaknesses.”
“It allows us to have a very simple understanding of the division of labor and responsibilities” he added. “We know what everyone works on, and there's deep mutual respect around the executive table for everyone’s skill set.”
His final advice for managers? Be open and honest. Leaders who prove a sense of vulnerability and reveal a more personal side to themselves can allow for much more open dialogue across the organization. It increases trust, drives innovation, and can help create a psychologically safe space at work.
“We're all better off when we take off the strong, iron facade, and speak with more vulnerability around how we're feeling,” he said.
