Shopify's Harley Finkelstein answers 5 questions about the future of work

By Mike Foster

Are you worried that artificial intelligence (AI) and increased automation will make your hard-earned degree obsolete? It might be time to unleash your inner entrepreneur and use AI to give your career superpowers, says Harley Finkelstein, Chief Operating Officer (COO) at Shopify, a leading cloud-based, commercial platform that has seen explosive growth.

Finkelstein (LLB and MBA ’09), a lawyer and entrepreneur, started his first business at age 17, selling T-shirts. After moving to Ottawa in 2005, he began attending meetings with a group of like-minded entrepreneurs. Among them was Tobias Lütke, who would soon realize that the software behind his online snowboard store had huge potential. Lütke went on to cofound Shopify, and Finkelstein became one of his first customers, using the platform to sell licensed T-shirts online. After completing his joint degree in law and business at the University of Ottawa, Finkelstein became Shopify’s Chief Platform Officer in 2010. He now serves as Shopify’s COO and hunts for promising tech start-up investments as an advisor for Felicis Ventures and OMERS Ventures. Finkelstein also sits on CBC’s Board of Directors. In 2017, he received the Canadian Angel Investor of the Year Award and was named one of Canada’s Top 40 Under 40.

As a key witness to the revolutionary change that digitization has brought to the workplace, Finkelstein shared his thoughts at the Chancellor’s Debate on The Future of Work: How will automation, artificial intelligence and tech trends reshape the jobs of the future. We asked him five questions about the future of work.

A recent report by the U.S. Department of Labour stated that 65% of today’s schoolchildren will be working in jobs that don’t exist yet. In this context, what is your vision of the future of work?

One area where I believe there will be an explosion is the commercialization of hobbies. Many of our parents and grandparents had hobbies. Maybe they made toys, or were carpenters, or made music. None of them felt they could make their hobby their full-time job. Technology now allows this. We will move away from this idea of work-life balance, where work and life are two separate things, to this idea of work-life harmony, where you fill your life up with things you absolutely love doing and that can also pay your bills.

What are your thoughts on the impact of artificial intelligence and automation?

I think AI will give almost every profession superpowers. We’re on the precipice of this right now. A lawyer can do research but AI can do better research; faster and more precisely. There will be jobs for lawyers because I think the ability to negotiate, argue and think critically is so innate to human beings. But imagine every lawyer has an AI tool, like Ross Intelligence, which helps expedite the research to build case law. AI is going to provide just about anyone with tools that traditionally only the biggest, wealthiest companies with the biggest teams were able to afford.

Is entrepreneurship something people are born with or can it be learned?

Everyone is born with ambition, nobody is born an entrepreneur. Entrepreneurship is the conversion of ambition into value creation. When you are a student, it is easier to explore new things. If you want to be a writer, try writing a blog while you’re in school; if you think entrepreneurship is something you might like, maybe start a little business. Leveraging the academic environment is something I did. In my case, my teachers were my board of directors and advisors, my classmates were my beta-testers and the academic buildings were my offices.

What tech trends are in play in e-commerce right now?

Personalization is a big one. Everyone’s experience of purchasing a product online, from an online store, Instagram or Pinterest, will become increasingly unique to that consumer. A second thing is Augmented Reality (AR), the ability to see what products will physically look like in your own home using your mobile phone. Imagine you don’t have to walk into a tailor anymore but using your phone and a mirror you can have everything fitted for you. We’re already experimenting with this at Shopify.

How can students and new grads future-proof their careers as technological advances rapidly alter the job market?

At my core, I always looked at education as a set of skills and tools, not a ticket to buy myself into a job. I think it behooves students, new grads and anyone in 2018, to know what they want out of life longer term. They should be self-aware to the extent that they know what gets them excited. People today want to create their own dream, they want to find their life’s work. Also, I think the language of the world will become computer programming.

Find out more about what jobs will look like in 2040 by catching up on a video of the conversation between Harley Finkelstein and uOttawa Chancellor Calin Rovinescu, which took place on March 29, 2018.