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Shopify’s Harley Finkelstein on leading with impact

Oct 6, 2021

What started as a means of survival led to a movement to break barriers for entrepreneurs around the world.

For the 15th anniversary of the Thomas d’Aquino Lecture on Leadership, Shopify President Harley Finkelstein shared the story of how he went from being one of Shopify’s first merchants – selling T-shirts to support himself through university – to the face of the brand. And although the lecture was pre-recorded, he made a surprise virtual appearance to chat with HBA1 students during the Q&A portion.

Originally working at a law firm after university, Finkelstein said he changed course after realizing Shopify’s potential and pitched to Founder and CEO Tobi Lütke how the company could disrupt e-commerce. That conversation led to Finkelstein being hired as Shopify's Chief Platform Officer.

“For so long, entrepreneurship and business-creation was really out of the hands of most people. It was too expensive, too complicated and we want to level the playing field,” he said. “It became clear that what we are building here can actually have a really big, meaningful impact on the world.”

Finkelstein discussed how maintaining meaningful impact, building a dynamic corporate culture, and finding his “superpower” contributed to Shopify’s success. Shopify is now one of the world’s largest e-commerce companies and Finkelstein was recently named to Fortune’s 2021 40 Under 40.

Here are some of the lessons he shared.

Focus on adding value

Creating a successful company isn’t about high returns; it’s about having a meaningful mission that motivates people to bring their best every day. Finkelstein said he recalibrates Shopify every year to ensure it still adds value, encourages employees to challenge the executive team, and organizes frequent hack sessions to generate new ideas. By removing what he calls “traditional politics,” the company operates like a high-performance sports team.

“A high-performance sports team doesn’t care how long you’ve been on the team … but which person has the best arms to throw the football,” he said.

Build a dynamic culture

A company’s culture isn’t about perks or a sign on the wall. Finkelstein said it’s about how people operate and what they care about when no one is watching. Having a mission that employees believe in and celebrating each employee’s strengths is key.

“The culture at Shopify is not the input of the leadership team, it’s a proxy of everyone who works there. Our culture has only gotten better because we’re not trying to hold onto any status quo culture, we're letting it develop,” he said. “Most people feel that culture is cemented – it’s static. I would argue it’s absolutely dynamic – it’s a living tree. With every new person that joins the company, the average quality goes up, but also the culture develops in a much better way.”

Hire people who are smarter than you

Finkelstein said he used to be insecure about hiring people who are smarter than him, but now he makes a list of things he’s not good at and hires people who excel at them.

“It’s not about being well-rounded, but rather finding people who are better at our weaknesses so we can sharpen our tools around our strengths,” he said. “Together we create this wonderful dynamic whereby we’re all focusing on our strengths and building good things together.”

Be comfortable being uncomfortable

Finkelstein said someone once told him an easy decision makes for a hard life, but a difficult decision can ultimately make life easier. Taking this advice to heart has allowed him to become a better version of himself.

“I think the magic happens when you put yourself in a position where you don’t feel comfortable – you don’t feel safe all the time,” he said. “That’s where you feel the most authentic. That’s where you can do the coolest things.”

Find and keep your ambition

Don’t shy away from challenges, embrace them because they’ll help you maintain your ambition. Finkelstein said consistent ambition levels remind you why you’re doing the work in the first place.

“I think it’s more impressive when someone gets punched in the nose time and time again – things don’t go well, yet they still keep getting up because that ambition drives them,” he said. “Ambition … if you sustain it over time, your propensity to succeed will be dramatically higher.”

That said, he prioritizes self-care – whether it’s fasting, exercise, meditation, or spending time with family – so he can keep his ambition.

Hone your personal superpower

Finkelstein said he has long struggled with anxiety and initially tried to get rid of it – until he realized he can channel it to be a strength, not a weakness. Being anxious before a television show appearance or presentation forces him to spend more time on his data points and story arc so he can excel.

“It feel like it’s game time. The anxiety – it drives me and allows me to really hone my skills and be like a sharpshooter – a sniper,” he said.

Finkelstein encouraged the students to speak openly about their perceived weaknesses to get the input needed to turn them into powerful tools.

“I was insecure about sharing the struggles that I've had with mental health with the world because I thought it showed weakness. But as I’ve learned and grown as a human and as a leader, I’ve realized that vulnerability is actually a sign of strength, not weakness.”

Embrace diversity and inclusion 

Since more than 50 per cent of Shopify’s merchants are women, a diverse leadership table is critical. But rather than just having a diversity policy or checklist, Finkelstein said companies should embrace diversity of thought and experiences as a competitive advantage.

“My diversity – my own experience – gives me a limited view,” he said. “If I want to be a global company, not only do I need to have diversity across gender and race, I need to have diversity in terms of experience.”

Show your best face during a crisis

When asked about leading during a crisis, Finkelstein pointed to a current example – the COVID-19 pandemic. Whether it was selling gift cards and helping Shopify’s merchants with curbside pickup, or giving employees time off and supplementing their home office costs, Shopify strove to be its best at the worst of times.

“I’m really proud of how we showed up both internally and externally,” said Finkelstein. “That’s when a company should be judged, not when coming off their best quarter when everything is going great. You need to be judged when things are going sideways. And I’m proud of how we showed up during those times. ”

The Lecture on Leadership, supported by the Ian O. Ihnatowycz Institute for Leadership, was established in 2006 to salute Thomas d’Aquino’s outstanding contributions to national and international business, public policy and the voluntary sector.