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Harley Finkelstein

Chief Operating Officer at Shopify

Harley’s charm, wit and youthful entrepreneurial spirit brings a great energy to conferences and events across the country. His personal philosophy is about ‘the hustle’. Go hard, go fast, build the best and execute.

Ottawa, Ontario, Canada


On The Hustle – don’t settle for mediocrity
Finkelstein believes the real path to success and upward mobility stems from merit  and an ability to better execute. While with experience comes expertise, organizations shouldn’t focus solely on longevity criteria when evaluating team members, projects or your organization’s future.  The person or company with the best product, service, or offering will ultimately win. So hustle, execute and win!

For Campuses:  Textbook to Checkbook
Finkelstein was an entrepreneur even while in school.  Among the lessons learned, he talks about balance, networks and the value of failure along the way.   “Balance is everything, you need to give 100% to both your education and your business;”  this is a skill set that he continues to work on daily.

The Future of Retail & E-Commerce
The view of the future is not one where online and offline are separate, but it all being commerce. Whether you buy it in a store and have it shipped to you, or you buy online and pick it up in a store,  the future of retail is going to be in commerce in general, not a separation of online and offline.  Right now 5% of retail sales are done online in Canada, and that’s going to grow very rapidly. Currently we have brick and mortar and we have “click”.  Finkelstein shows how the future is “brick and click” whereby retailers sell online and off-line.  Are you ready?

Platform Plus

Panelist/In Conversation


Candian Startup Awards | Angel Investor of the Year
Ottawa Business Journal | Newsmaker of the year
BOB Newsmaker of the Year

PROFIT Magazine Canada’s Smartest Company (Shopify)

  • Harley's presentation was captivating, he really had everyone's attention! I would definitely recommend him to another association who is search for an entrepreneur to speak at their event. He was an overall good guy, with a great personality and showcased a great amount of knowledge about the industry.

    - Information Technologies Association of PEI
  • That was amazing. People are reeling from that. One participant said that her colleagues will be very jealous that they were not there. People are disappointed that you will not be at the Embassy - however, you would probably get mobbed and cornered for the evening.

    - Project Manager, University of Ottawa, Telfer School of Management
  • The youth kept raving after about how inspiring you were. Even my boyfriend who finds this volunteer stuff of mine boring could not stop talking about how great your story was!

    - Project Manager, IC Change (ICC), SIFE Carleton
  • Delegates LOVED your talk and many have come up to me saying they want to work for you as well. They really appreciated how authentic you are and the practical lessons you shared.

    - Nspire Innovation Network

Summary Profile

Harley Finkelstein knows what it means to hustle and he enjoys every minute of it. Harley is an entrepreneur and Chief Operating Officer (COO) at ‘Canada’s Smartest Company’ (Profit magazine, 2012) – Shopify. Harley was directly hired by Canadian CEO of the year Tobi Lütke to become comfortable with being uncomfortable.

Shopify was also named by FastCompany as ‘one of the world’s most innovative companies’ ranking in the top 10 of innovative online retailers. Shopify is one of the world’s leading ecommerce website solution that includes everything you need to run an online store and is growing in leaps and bounds.

In 2018, Shopify expected revenues of over $1billion. His personal philosophy is about ‘the hustle’.  Go hard, go fast, build the best and execute. Finkelstein stared his first company at age 17 while a student at McGill. Seeing opportunity to sell T-shirts to the university he went bought a screen printing machine, started calling the executive council and soon landed the contract to supply the school with 200 T-shirts. Fast-forward to three years later, he was supplying apparel to over 50 universities across the country.

He’s become a lawyer after completing his law degree as well as his MBA at the University of Ottawa, where he co-founded the JD/MBA Student Society and the Canadian MBA Oath. Additionally, Harley’s served as a mentor and advisor to a number of entrepreneurial organizations and incubators, including FounderFuel, ExtremeStartups, CYBF, OCRI & CIPPIC. Harley’s charm, wit and entrepreneurial spirit brings a great energy to conferences and events across the country. Harley became one of two new Dragons added to CBC’s Next Gen Den for season 2 of the show.