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The "Leak" Edition
Why? It offers one of the clearest executive positions I’ve seen on AI adoption inside a company. And for me, this means a glimpse into the future.
I know what you're thinking: "My company is not Shopify. I work in Retail, Banking, Pharma, or CPG. This doesn’t apply to me."
But stay with me. I promise it's going to matter to you.
Here's what the memo said, why it matters, and what we as leaders can learn from it:
What Tobi said:
“Using AI effectively is now a fundamental expectation of everyone at Shopify... Stagnation is almost certain, and stagnation is slow-motion failure. If you're not climbing, you're sliding.”
What it means: This isn’t a suggestion. Shopify has made AI fluency part of the job description - for everyone. Not as a specialized skill, but a basic one.
My take: Most companies still treat AI like a side project or innovation experiment - something we outsource to another department or individual. We need to stop asking “who owns AI?” and start asking as leaders: “How do we build this into every role in my department and company?”
What Tobi said:
“The prototype phase of any GSD project should be dominated by AI exploration... you can learn to produce something others can use and reason about in a fraction of the time.”
What it means: AI is meant to be part of idea generation, testing, early-stage thinking, and final delivery.
My take: It’s great to use AI as a productivity tool - but also as a creative partner. Use it earlier - when ideas are still forming.
What Tobi said:
“We will add AI usage questions to our performance and peer review questionnaire... Learning to use AI well is an unobvious skill.”
What it means: AI skills aren’t just something you build in your spare time. Shopify is formally measuring how well employees prompt, explore, and integrate AI into their work.
My take: Companies will start assessing AI usage like they do communication or collaboration. It creates real accountability. And it sets a clear signal - AI isn’t a bonus. It’s a baseline.
But here's the thing - if we assess people, we also need to be responsible for giving them the tools and resources to become AI literate.
What Tobi said:
“You have access to as much of the cutting edge AI tools as possible. Slack and Vault have lots of places where people share prompts that they developed, like #revenue-ai-use-cases and #ai-centaurs. We’ll learn and adapt together as a team.”
What it means: Shopify wants AI learning to be communal, with teams sharing prompts, lessons, failures, and breakthroughs. Experiment freely - but don’t do it in isolation.
My take: We should ask ourselves: Do we have places for people to share what they’re trying? Building capability means igniting a spark in people - who then share with and build each other up along the way.
What Tobi said:
“Before asking for more headcount and resources, teams must demonstrate why they cannot get what they want done using AI.”
What it means: AI is becoming a strategic lens for rethinking how work is done. Before hiring, Shopify wants teams to imagine what the work could look like with AI tools or autonomous agents in the mix.
My take: This is one of the hardest - and most important - questions we’ll need to ask in the coming months and years. The shift is from “who can we hire?” to “what can we reimagine?”
There’s no point in throwing technology at broken processes. The real work starts when we rethink and redesign those processes from the ground up.
This is what AI adoption looks like. Not a pilot. Not a fancy press release. Not a future ambition. It’s happening, now, and led from the top.
This memo reframes AI as a core part of how modern work happens.
So we need to ask new kinds of questions.
What does your next hire look like if you had an AI teammate? What if every project started with an AI-powered prototype? What if prompt crafting became as important as PowerPoint?
This is the kind of thinking that gets us all ready - leaders and teams - for what's already here.
I’ll see you next week.
