Helping Shopify employees game their AI promotion criteria

Shopify's CEO just announced that AI usage is expected of employees, and they will get peer feedback on AI usage. So why not help them out and brainstorm how they can game it.

Shopify’s CEO, Tobi Lutke, posted a company-wide memo declaring that using AI is now expected of Shopify employees.

After it leaked, he posted it to X/Twitter in its entirety. The full memo is quite long, so below is the most important section.

What This Means

1. Using AI 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 AI 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. AI must be part of your GSD Prototype phase. The prototype phase of any GSD project should be dominated by AI exploration. Prototypes are meant for learning and creating information. AI 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 AI usage questions to our performance and peer review questionnaire. Learning to use AI 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 AI 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 AI capabilities, and we’ll dedicate time to AI 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 AI. What would this area look like if autonomous AI agents were already part of the team? This question can lead to really fun discussions and projects.

I’ve previously written about gaming performance management criteria at big companies, which is where you selectively overperform on tasks that are valued by the promotion criteria, and try to avoid doing anything that is not rewarded by the promotion criteria.

Throughout the past 20 years, there have been common playbooks for gaming promotions in big companies. For example: let’s say that you’re a manager and you want to get promoted to director or higher. Career ladders normally say that as you get promoted, you will be managing progressively larger teams (or teams of teams). The naive approach is to deliver impact with your small team and then gradually get more engineers under you as you gain trust.

But that will take a long time. Let’s game the promotion criteria. Isn’t it better to find a company priority and work on some critical functionality for the success of the initiative, and use that position to argue for as much headcount as possible¹? As the team grows, you can even convince some engineers under you to become managers of a few employees each. Boom! Suddenly you’re managing a team that a normally a director would. If you don’t mess up the execution, you’re a shoo-in for that promotion.

But the AI trend will require us to find new ways to game promotion criteria. So I want to help all of the Shopify employees that are now figuring out what this means. Obviously I don’t have access to your career ladder. But I have access to that memo and I’m feeling spicy. Let’s brainstorm ways that career-minded Shopify employees can game their promotion system.

First, let’s look at “AI values” that the memo calls out.

• A good Shopify employee…

  • Uses AI to get 100x the work done

  • Improves by 20-40% every year

  • Learns from other Shopify employees

  • Follows the Shopify values “Be a constant learner” and “thrive on change”

• A good team…

  • Uses AI during their “Get shit done” prototyping phase

  • Can demonstrate why AI cannot perform the work they want from a new headcount

• The performance review process…

  • Will have AI usage questions on their performance and peer-review questionnaire

  • Will explicitly involve getting feedback from peers on AI usage

Okay, first things first: make sure that an AI agent can’t replace you. Can it give engineering feedback on designs and product specs? Can it take a design and product spec and produce an engineering spec? Can it produce code from the product spec? Can it write tests for that code? Can it fix code based on comments on your PR?

Is your job safe? Great! Let’s become a 100x AI-powered engineer.

We know that sharing knowledge is important. Document what it can and cannot do. I don’t know what Shopify uses. Google Docs? Notion? Cram your findings into there and share this with your immediate team.

First, it’s clear that Tobi wants the company to use AI to rapidly prototype. Does vibe coding come naturally to you? No? Then you need to find someone who will teach you. And here’s the trick: instead of just having them show you, have them give a public demo. Be the person who asks in a Slack channel, “hey, @soandso is going to demo how they build large prototypes quickly in Cursor. DM me if you have something neat you’d like to present, and react :raised-hand: if you want an invite.”

Why would you set up a meeting? Because there are going to be peer review questions involving the use of AI. You want to remind your coworkers early-and-often that you are a 100x AI Engineer.

Now that you know how to prototype rapidly using AI, use that knowledge to show everyone that you are a 100x AI engineer. Build an “AI Solutions” site. Why? As an outsider, I noticed that Tobi referenced Slack channels as the knowledge repositories for prompting. Slack is a great place to coordinate work and shitpost, and a bad place to store persisted instititutional memory. So you’re going to have the AI spit out an internal website. Index it by outcome (prototype, debugging, etc). Your first story will be a prototyping story showing the prompts you used to build the prototyping site. Next you’re going to add the example from the @soandso talk you organized. And then finally you’re going to have an AI scrape all of the messages from that Slack channel to fill out content. Remember: we’re being a 100x engineer, so if it sounds hard you’re just going to throw the AI at it.

Go ahead and share your new prototype site in the Slack channels where people have been collecting prompts. Mention that anyone who wants to add one should reach out to you. At this point, you have the option to never think about this again. Well, you should probably present it to your team or group or whatever. Who will be writing your peer reviews for your performance review? Make sure that they are all included in that group.

Now let’s look at your current project. What are the parts that you’re ashamed of? What are the parts that kinda suck? Try to throw AI at it and see what sticks. We’re trying to 100x, so don’t waste your time if it’s not working out. If something doesn’t look promising just immediately bin it.

Do your services have the READMEs they should? Well, they do now! Give Cursor some of the important files in your service and an example README and it’ll spit out a pretty reasonable one. Just fix it up and send it out.

Point it to particularly fragile parts of your project and ask it “what are the most likely bugs in this project?” and “how can this be refactored so that it is easier to modify X?”

If anything actually works, make sure you make a big deal about how you generated it with AI. You can even mention it in the commit message or the PR description’s body. Since you’re going to get peer review feedback on the use of AI, you want everyone to know that you are an AI engineer.

If you’re used to seeing people game promotion criteria in companies, this may look different than you’re used to! In most large companies you scale your impact with the size of the team or the value of the technical contribution. But in a regime where rapid prototyping and proper value sharing is important, you’re trying to scale your impact based on how much you can share without someone saying, “stop showing us all of this junk.”

1. If you want an alternative: you can create a newsletter, get all of your coworkers to subscribe, and then never shut up about generative AI.