Shopify recently welcomed Bret Taylor, a Silicon Valley executive and former co-CEO of Salesforce, to its Board of Directors. What caught my attention was the unusual move by Shopify to publish a one-hour video interview between Tobi Lütke and Bret Taylor. While it's interesting to learn about Bret, I found the discussion to be a valuable window into Tobi's mindset and Shopify's direction.

Here are my top takeaways:

1️⃣ Importance of Experimentation:

Tobi emphasized that in the early years of a company, trying various ideas is crucial. It's not always clear which ideas will lead to success and which won't. This humble reflection highlights Shopify's journey of discovering what truly matters —catching eCommerce lightning in a bottle, great software, an exceptional management team, or its focus on empowering entrepreneurs.

Shopify is still sorting these factors to answer the question: "What does Shopify need to do more of or less of in the future?"

2️⃣ The Tension Between Process and Innovation:

Tobi's worldview challenges the notion of traditional management processes as the key to improvement. He believes processes create unnecessary complexity and hinder success. This perspective stems from his hacker/developer background, where processes can be perceived as "cruft" that needs to be refactored out. Tobi's aversion to excessive "baby-proofing" reflects his dedication to fostering innovation and agility.

This is a stark contrast in methodology to Jeff Bezos who was meticulous in outlining his leadership principles, and setting up a "system of systems" within Amazon to govern improvements and planning of all kinds.

3️⃣ How Tobi Evaluates Software Products

Additionally, Tobi shared an intriguing perspective on the performance evaluation of Shopify's products. He judges their success by the quality of pull requests submitted to the Shopify code repository.

This emphasizes the significance of maintaining high coding standards and reinforces Tobi's commitment to curating the codebase—a top priority for him as CEO.

Lastly, Tobi stated that AI has shattered the limitations of building exceptional software, enabling Shopify to provide entrepreneurs with an infinitely patient, confident, and hard-working sidekick.

This statement crystallizes Shopify's mission—to empower entrepreneurs on their hero's journey.

In terms of Shopify's enterprise journey, it's challenging to see how it aligns with traditional enterprise software. Shopify's product seems better suited to organizations that share their mission, rather than trying to mold their thinking or product to fit traditional enterprise expectations.

The average enterprise company often has a fundamentally different worldview than Shopify, making it a better choice to focus on customers who resonate with their vision.