iiinova — where your digital self keeps evolving

Beccaneer @beccaneer.bsky.social · 08/04/2025

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Team, We are entering a time where more merchants and entrepreneurs could be created than any other in history. We often talk about bringing down
the complexity curve to allow more people to choose this as a career. Each step along the entrepreneurial path is rife with decisions requiring skill, judgement and knowledge. Having Al alongside the journey and increasingly doing not just the consultation, but also doing the work for
our merchants is a mindblowing step function change here. Our task here at Shopify is to make our software unquestionably the best canvas on which to develop the best businesses of the future. We do this by keeping everyone cutting edge and bringing all the best tools to bear so our merchants can be more successful than they themselves used to
imagine. For that we need to be absolutely ahead.
Reflexive Al usage is now a baseline expectation at Shopify Maybe you are already there and find this memo puzzling. In that case you already use Al as a thought partner, deep researcher, critic, tutor, or pair programmer. I use it all the time, but even I feel I'm only scratching the surface. It's the most rapid shift to how work is done that I've seen in my career and I've been pretty clear about my enthusiasm for it: you've
heard me talk about Al in weekly videos, podcasts, town halls, and... Summit! Last summer I used agents to create my talk, and presented
about that. I did this as a call to action and invitation for everyone to

tinker with Al, to dispel any scepticism or confusion that this matters at all levels. Many of you took up the call, and all of us who did have been in absolute awe of the new capabilities and tools that Al can deliver to
augment our skills, crafts, and fill in our gaps. What we have learned so far is that using Al well is a skill that needs to
be carefully learned by... using it a lot. It's just too unlike everything else. The call to tinker with it was the right one, but it was too much of a suggestion. This is what I want to change here today. We also learned that, as opposed to most tools, Al acts as a multiplier. We are all lucky to work with some amazing colleagues, the kind who contribute 10X of what was previously thought possible. It's my favorite thing about this company. And what's even more amazing is that, for the first time, we see the tools become 10X themselves. I've seen many of these people approach implausible tasks, ones we wouldn't even have chosen to tackle before, with reflexive and brilliant usage of Al to get 100X the work
done. In my On Leadership memo years ago, I described Shopify as a red queen race based on the Alice in Wonderland story—you have to keep running just to stay still. In a company growing 20-40% year over year, you must improve by at least that every year just to re-qualify. This goes
for me as well as everyone else. This sounds daunting, but given the nature of the tools, this doesn't even sound terribly ambitious to me anymore. It's also exactly the kind of environment that our top performers tell us they want. Learning together, surrounded by people who also are on their own journey of personal growth and working on worthwhile, meaningful, and hard problems is precisely the environment Shopify was created to provide. This represents both an opportunity and a requirement, deeply connected to our core values of Be a Constant Learner and Thrive on Change

$. These aren't just aspirational phrases-they're fundamental expectations that come with being a part of this world-class team. This is what we founders wanted, and this is what we built.What This Means 1. Using Al effectively is now a fundamental expectation of everyone at Shopify. It's a tool of all trades today, and will only grow in importance. Frankly, I don't think it's feasible to opt out of learning the skill of applying Al in your craft; you are welcome to try, but I want to be honest I cannot see this working out today, and definitely not tomorrow. Stagnation is almost certain, and stagnation is slow-motion failure. If you're not climbing, you're sliding. 2. Al must be part of your GSD Prototype phase. The prototype phase of any GSD project should be dominated by Al exploration. Prototypes are meant for learning and creating information. Al dramatically accelerates this process. You can learn to produce something that other team mates can look at, use, and reason about in a fraction of the time it used to take. 3. We will add Al usage questions to our performance and peer review questionnaire. Learning to use Al well is an unobvious skill. My sense is that a lot of people give up after writing a prompt and not getting the ideal thing back immediately. Learning to prompt and load context is important, and getting peers to provide feedback on how this is going will be valuable. 4. Learning is self directed, but share what you learned. You have access to as much of the cutting edge Al tools as possible. There is chat.shopify.io, which we had for years now. Developers have proxy, Copilot, Cursor, Claude code, all pre- tooled and ready to go. We'll learn and adapt together as a team. We'll be sharing Ws (and Ls!) with each other as we experiment with new Al capabilities, and we'll dedicate time to Al integration in our monthly business reviews and product development cycles. Slack and Vault have lots of places where people share prompts that they developed,$

like #revenue-ai-use-cases and #ai-centaurs. 5. Before asking for more Headcount and resources, teams must
demonstrate why they cannot get what they want done using Al. What would this area look like if autonomous Al agents were already part of the team? This question can lead to really fun
discussions and projects. 6. Everyone means everyone. This applies to all of us-including
me and the executive team.
The Path Forward Al will totally change Shopify, our work, and the rest of our lives. We're all in on this! I couldn't think of a better place to be part of this truly unprecedented change than being here. You don't just get a front-row seat, but are surrounded by a whole company learning and pushing
things forward together. Our job is to figure out what entrepreneurship looks like in a world where Al is universally available. And I intend for us to do the best possible job of that, and to do that I need everyone's help. I already laid out a lot of the Al projects in the themes this year-our roadmap is clear, and our product will better match our mission. What we need to succeed is our collective sum total skill and ambition at applying our craft, multiplied by
Al, for the benefit of our merchants.
-tobi
CEO Shopify

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