Shopify’s Harley Finkelstein On Asking For Forgiveness Instead of Permission

The Chief Platform Officer of ecommerce site Shopify shares what he looks for in new hires, how to get everyone to share ideas and why he’s had an executive coach for years.

One good way to truly understand a business is to start as a customer. In 2005, to put himself through law school, Harley Finkelstein sold T-shirts on Shopify. Today, as the company’s chief platform officer, Finkelstein is helping to grow the popular e-commerce solution into a much broader commerce solution, so the company can get a piece of the retail pie both online and offline.


With more than 300 employees (and growing), Finkelstein is committed to building an environment where everyone can have their say. Shopify regularly holds town hall meetings so his team always has a forum for compliments and complaints.

Harley Finkelstein

When searching for new candidates, the 30-year-old executive is on the look-out for one important trait: resourcefulness. As for how Finkelstein keeps himself focused and motivated, during our interview he shares that he has been working with an executive coach for the past three years. He also admits that his days are filled with a whole lot of hustle, failing fast and failing gracefully, and asking for forgiveness instead of permission.

About the author

Amber Mac is a bestselling author, TV host, speaker, and strategist. She has worked as a technology TV host with tech guru Leo Laporte on G4TechTV and currently co-hosts a popular show on Laporte's network.