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.

🔗 LinkedIn | Website

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.