Ep.517- FAN FAVORITE | Harley Finkelstein – Inside the $100B Growth Strategy That Built Shopify
Second in Command: The Chief Behind the Chief with Cameron Herold
Second in Command with Cameron Herold
4.9 • 225 Ratings
🗓️ 9 October 2025
⏱️ 46 minutes
🧾️ Download transcript
Summary
What does it take to help build one of the most influential e-commerce companies in the world?
In this Fan Favorite episode, Cameron Herold sits down with Harley Finkelstein, President and COO of Shopify, to revisit one of the most downloaded and talked-about conversations in the show’s history.
Harley shares his journey from law school student to serial entrepreneur to becoming the operational powerhouse behind Shopify’s global rise. He opens up about working alongside founder Tobias Lütke, building the company’s culture from the inside out, and leading through rapid growth and constant reinvention.
Whether you’re scaling a startup or steering a billion-dollar brand, Harley’s insights on leadership, culture, and staying grounded in the middle of explosive success will challenge and inspire you.
About the Guest
Harley Finkelstein is the President and Chief Operating Officer of Shopify, where he’s played a pivotal role in scaling the company from startup to a global leader in e-commerce. A serial entrepreneur and public speaker, Harley is also on the board of C100, an advisor to major venture funds, and a familiar face as a dragon on CBC’s Dragons’ Den.
Resources & Mentions
- Good to Great by Jim Collins
- The Misunderstood Role of the COO – Harvard Business Review
- Rocket Fuel by Gino Wickman
- Riding Shotgun: The Role of the COO by Nathan Bennett & Stephen Miles
- Maker’s Schedule, Manager’s Schedule – Paul Graham essay
Important Links
- Connect with Cameron: Website | LinkedIn
- Explore the COO Alliance - The World’s Leading Community for Seconds in Command
- Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
- Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
- Chat or video call with AI Cameron via Delphi
Note: This Fan Favorite episode is a recast of one of our most impactful interviews, still packed with insights for second-in-command leaders. Whether it’s your first listen or a revisit, there’s timeless value inside.
The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.
Transcript
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| 0:00.0 | Hey there, just a quick note before we dive in. This is actually one of our older episodes, but we're bringing it back because it's one of the most downloaded ones we've ever released. Clearly, it struck a chord with a lot of listeners, and I know there's so much value packed inside. So whether you're hearing it for the first time or revisiting it, enjoy this fan favorite. Every year, my job completely changes. So whether that's, hey, I got to get really |
| 0:22.2 | good at fundraising or I get it really good at building a sales award or I get really good at hiring |
| 0:25.6 | the most talented people and coaching them from the biggest companies in the planet or in 2015, |
| 0:31.0 | I had to get really good at taking a company public. |
| 0:46.6 | Welcome to the Second in Command podcast, produced by the C.O. Alliance and brought to you by its founder, Cameron Harold. |
| 0:55.9 | In the Second in Command podcast, we talk to top COos who share the insights, strategies, and tactics that made them the chief behind the chief. |
| 0:59.3 | And now, here's your host, Cameron Harold. |
| 1:05.1 | Today we're talking with Harley Finkelstein. |
| 1:08.7 | Harley is a Canadian businessman, entrepreneur, and public speaker. |
| 1:12.1 | He's also the best known as the chief operating officer for Shopify. He's on the board of the C-100 and an advisor to both Omer's Ventures and |
| 1:18.8 | malicious ventures. He's also a dragon on CBC Dragons Den, which is the Canadian version of Shark Tank. |
| 1:24.6 | In his early life, Harley was born and raised in Montreal, Canada, |
| 1:29.0 | and at 17, he found that a T-shirt company while attending McGill University, later transferred to |
| 1:34.0 | Concordia University and received his bachelor's degree in economics. He then attended the University |
| 1:39.0 | of Ottawa, where he founded the Law MBA Society and also the Canadian MBA oath while working towards his law degree and his MBA. |
| 1:48.6 | After completing both his law degree and his MBA, Harley worked at a law firm in Toronto for a year. |
| 1:53.6 | And then in 2009, he met Tobias, who is the CEO of Shopify, and they started talking about opportunities for the company. |
| 2:00.3 | Harley was then hired soon after that and was named the chief platform officer. |
| 2:05.9 | And in 2014, Harley was appointed as a member of the C-100 board. |
| 2:10.8 | The C-100 is an organization that supports Canadian technology companies |
| 2:14.3 | as a bridge between Canada and the Silicon Valley. |
| 2:19.8 | In 2016, Harley was named the C-O-O of Shopify. That same year, he was inducted into the Order of Ottawa by Mayor Jim Watson. |
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