Harley Finkelstein

From Grokipedia

Harley Finkelstein is a Canadian entrepreneur, lawyer, and business executive serving as the President of Shopify Inc., where he oversees the company's commercial teams, growth initiatives, and external affairs.

Born in Montreal, Quebec, Canada, and raised in South Florida, United States, Finkelstein demonstrated early entrepreneurial drive by founding his first company at age 17 while studying at McGill University in Montreal. He later pursued advanced education at the University of Ottawa, earning both a law degree and an MBA, during which he co-founded the JD/MBA Student Society and the Canadian MBA Oath. Following his studies, Finkelstein practiced law and became an active angel investor, earning recognition as the Canadian Angel Investor of the Year in 2017.

Finkelstein joined Shopify in 2010 as Chief Platform Officer, initially handling a broad range of responsibilities including business development, legal affairs, and finance. He advanced to Chief Operating Officer in 2016, managing areas such as sales, partnerships, and the app store, before transitioning to President in 2020 to focus on accelerating the company's expansion and merchant success. Under his leadership, Shopify has solidified its position as a global leader in e-commerce, powering millions of businesses and achieving record financial performance, including strong growth in Q3 2025.

Beyond his role at Shopify, Finkelstein is a prominent public speaker, podcast creator—hosting the Big Shot series featuring entrepreneurial stories—and board member for organizations including the National Retail Federation, Operation HOPE, and the Montreal Children's Hospital Foundation. His contributions to business and community have been honored with awards such as Canada's Top 40 Under 40 in 2017, Fortune's 40 Under 40, the Order of Ottawa in 2016, and the King Charles III Coronation Medal.

In brief

Harley Finkelstein was born in Montreal to a Jewish family, the grandson of Hungarian Holocaust survivors who later ran a market stall after arriving in Canada. He DJed as a teenager, started a T-shirt company at seventeen, and earned a law degree and MBA at the University of Ottawa while selling online as one of Shopify’s first merchants.

He joined Shopify in 2010 and rose from chief platform officer to president, helping merchants sell across a worldwide network. Off the job he hosts the Big Shot conversations with Jewish entrepreneurs and funded a Chabad student center in Ottawa. The family story — survival, a stall, a company — is the one he tells most often.