Almost four and a half years ago in early 2021, I went to work at Shopify as Technical Advisor to the CEO. And, I have to say, it was one of the best jobs I’ve had. It’s like it was custom made, just for me. Working alongside Tobi Lütke as a right hand advisor meant that I was part of almost every major technical discussion and had a very close up view of how a hundred-billion dollar company works while retaining its founder-mode ambitions and flexibility.

From helping to define and prototype Hydrogen and Oxygen, Shopify’s headless e-commerce stack, to changing Shopify’s compensation strategy with Flex Comp, there weren’t too many things that I didn’t have visibility and input into. And, as Vice President of Developer Productivity, I helped with Shopify’s push to use AI and LLMs, including helping to rollout Claude Code internally when it was first launched.

Of course, not every day was great. There were two major layoffs and the divestiture of Shopify Logistics, none of which were easy. But easy isn’t part of the job description. Every challenge required applying my skillset in a new and interesting way. And grow new skills quickly as needed.

I said more than once that working at Shopify was the best MBA I could have gotten, and it came with direct experience (and a paycheck!) attached. But, like studying for a degree or serving a tour of duty, there’s a time when you know it’s done and you need to take the next step. As companies evolve, so do the roles within them.

Last week, I served my last day at Shopify. Today, I’m a free agent.

Why? There are several reasons, big and small. Not many really matter in the long view. The one I’ll share here — probably the most important one when all is said and done — is that the world is changing thanks to AI. It's like 1997 and the early web all over again. But different, and more extreme. Of course, like then, many will be looking for a free lunch or to create party tricks. And, like the web, it’ll take us a while to really figure out how it’s going to change the world. For those that invest the time and effort, however, entirely new horizons are opening up even as entire industries are about to be rewritten.

So, I’m taking my virtual degree from the School of Shopify and heading into the world. Instead of lining up my next role before leaving, I’m going to take a few months this summer to really reflect on what I’ve learned and what I want to take forward with me. And, I want to step back and do that reflection outside the scope of any single company’s perspective.

It’s time to Observe and Orient. Decision and Action will come soon enough.