Every CEO Is Writing the Same AI Memo. Here’s What They’re Really Saying.

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Your CEO is about to write an AI memo.

I know because I've been collecting them like disaster preparedness manuals, and they're multiplying faster than ChatGPT responses. It’s a professional survival instinct: If I know what these CEOs want, I’ll be able to give it to them—and I’ll be safe from this particular flavor of apocalypse.

Barely a week goes by without another internal memo screenshot rocketing across X or LinkedIn, mixing optimism about what AI promises with urgency about what it portends. The results come across as part pep talk, part ultimatum: Get fluent with AI, or get left behind.

It all kicked off when Shopify CEO Tobi Lütke posted his memo to X, declaring that "reflexive AI usage is now a baseline expectation” at the e-commerce giant. Within weeks, similar manifestos emerged from Duolingo, Box, Fiverr, and Walleye Capital. The speed of the cascade itself is a signal: AI sophistication has reached a point where CEOs feel compelled to act. Fast.

These aren't just corporate communications; they're cultural artifacts—real-time documentation of how organizations are processing the biggest shift in knowledge work since we all got email addresses. Digital archeologists of the future will look at documents like these as they piece together the story of how people navigated the earliest days of AI in the workplace.

So why wait? Let's see what these memos reveal about where work is headed, what leaders really mean when they say "be AI-first," and—most importantly—how to navigate the productive tension between executive vision and ground-level reality. Because mark my words: If your CEO hasn’t sent out the “AI memo” or some kind of directive about how AI is or isn’t to be deployed, they’re about to. May this survey help you prepare.

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Messaging: What CEOs want you to know

Reading these memos back-to-back is like watching five directors tackle the same script. The plot points are identical—AI is here, we need to adapt, the future depends on it—but the emotional registers couldn't be more different.

On one end, there's Will England, CEO of hedge fund Walleye Capital (an Every Consulting client), practically vibrating with enthusiasm. ChatGPT isn't just a tool; it's a "magical elixir that makes you 20 percent smarter instantly." His memo reads like a tent revival for the algorithmically enhanced. "Not using these tools is like refusing to use the internet in 1995," he declares. "That's just dumb."

On the other end sits Fiverr's CEO Micha Kaufman, who opens with the rhetorical equivalent of a cold shower: "AI is coming for your jobs. Heck, it's coming for my job too." He suggests employees might need to "scream hard in front of the mirror" before getting to work. It's radical candor turned up to eleven—part motivational speech, part existential crisis.

Between these poles, the other CEOs strike different notes. Lütke wraps Shopify's mandate in philosophical metaphors about red queens and constant running. Box's CEO Aaron Levie stays pragmatically focused on eliminating "drudgery." Luis von Ahn at Duolingo took what seemed like the measured strategist approach, comparing AI to the company’s prescient mobile bet. (Note: Von Ahn has since reversed course on key parts of their memo after consumer backlash over plans to replace human contractors with AI.)

But look past the tonal differences and a unified message emerges. Every memo shares three core elements:

1. The inevitability narrative: This isn't optional. It's not a pilot program. It's happening, with or without you.
2. Personal testimony: Each CEO claims to use AI constantly. "I use it all the time, but even I feel I'm only scratching the surface," Lütke admits. They're modeling the behavior they expect—and admitting their own learning curves.
3. The paradox of urgency. Every CEO delivers the same contradiction: "We must move fast" coupled with "We're still figuring this out." It's a mandate wrapped in uncertainty—decisive action despite incomplete information.

These aren't stone tablets handed down from the C-suite. They're leaders thinking out loud about a transformation that's moving too fast for anyone to fully grasp it. The range of tones—from evangelical to apocalyptic—reveals just how much uncertainty lives beneath the surface of these seemingly definitive declarations.

Making it stick: Five companies, five experiments

If messaging reveals what CEOs are feeling, implementation shows what they actually value. The tactics they choose and outcomes they track expose their real priorities—and what they think AI adoption should look like. Here's what their approaches reveal.

Make AI part of your professional life

Lütke kicked off the memo trend by baking AI into Shopify's infrastructure. AI usage joins performance reviews, teams must prove they can't automate before getting headcount, and every project's prototype phase "should be dominated by AI exploration." The focus is on multiplier effects—top talent plus AI yielding "100x" gains. AI isn't an add-on anymore; it's how Shopify defines competence.

Use visibility to drive adoption (and competition)

Walleye Capital’s England turns adoption into a competitive sport: $25,000 bounties for tool suggestions, public leaderboards with "real cash prizes," weekly meetups. He's betting traders will refresh their ChatGPT stats like they track P&Ls. Success is simple—who's using it, how often, which departments lead. If you can gamify trading, you can gamify AI.

Turn efficiency into innovation

Levie frames AI as liberation from "drudgery" with a twist: Teams that automate keep the savings for strategic projects. It’s an approach built around incentives—giving teams an upside and a reason to engage. Box tracks how much faster ideas move from concept to execution. The bet: AI savings shouldn't return to the CFO—they should fund your next breakthrough.

Embrace radical change

Von Ahn at Duolingo takes the most aggressive stance: Phase out contractors for AI-capable work, make AI use part of hiring and reviews, prove automation before adding headcount. They're measuring transformation—which processes got rebuilt, how much content creation accelerated. The message: Don't tweak human systems, rebuild them (though von Ahn has since walked back parts after consumer backlash).

Create personal urgency

Kaufman offers to talk with Fiverr employees one-on-one about AI’s ramifications for their work, pushing individuals to become "prompt engineers" and "exceptional talents." No company metrics here—just personal transformation. Who's mastering their domain's AI tools? His framing is stark: Master AI or face "career change in a matter of months."

Notice what's missing across all five memos: traditional business metrics. No one's promising "20 percent productivity gains by Q3" or specific ROI targets—that is, not yet. They're tracking activity—usage, adoption, transformation.

This gap between mandate and measurement creates unexpected breathing room. While your CEO insists AI is urgent, they can't yet define what "winning" looks like. That uncertainty is your opportunity. You get to help write the success metrics, shape what "good" AI usage means in your role, and demonstrate value before it's codified into KPIs. By the time your company figures out what to measure, you'll already be the expert who helped define it.

The CEOs are essentially admitting: We don't know what we're optimizing for yet. We just know we need to move faster than competitors. Five experiments, five approaches. The variation itself is the message: We're all making this up as we go.

Your Monday morning game plan

Your CEO just dropped their AI manifesto, or you're sensing one brewing ahead of the next all-hands meeting. Here's how to navigate your organization's AI moment without waiting for someone to hand you a roadmap.

First, decode what your CEO is really anxious about. Is it competitive pressure (that “we can't miss this wave” energy that led Duolingo to move too fast)? Efficiency mandates (Box's "eliminate drudgery")? Existential positioning (Fiverr's "adapt or die")? The specific anxiety shapes the opportunity. If they're worried about competition, show them differentiation. If it's efficiency, show how AI multiplies your impact. If it's survival, prove irreplaceability.

Start documenting everything. Not just your wins—your experiments, failures, and half-baked theories. Public learning is the unlock. That quick prompt that saved you an hour? Write it down. The workflow that didn't quite work? Document why. You're not just building your own playbook; you're creating organizational knowledge.

Find your bridge role. The gap between executive vision and daily reality isn't empty space—it's where the real work happens. Maybe you become the translator who helps your team understand what "AI-first" means for their specific work. Maybe you're the experimenter who tests tools and shares what sticks. Maybe you're the skeptic who asks the hard questions that make implementations better.

Run weekly experiments. Pick one task you do regularly and try automating part of it. Not the whole thing—just one step. Share what you learn, especially the failures. Building "reflexive AI usage" isn't about perfection; it's about practice.

It’s our move now

What makes this moment remarkable is that leaders are mandating AI adoption while admitting they don't have all the answers. That admission creates an opening for everyone else. The rules are being written by whoever shows up to write them. Every prompt you craft, every workflow you reimagine, every experiment you run becomes part of your organization's AI playbook. You're not just following a transformation—you're designing it.

The most valuable employees right now might not be the ones with the most AI expertise. They're the ones who see the gap between what leadership imagines and what actually works—and who steps in to bridge it. They're turning vague mandates into practical systems, philosophical anxiety into actionable processes.

Whether your CEO's memo reads like a tech evangelist's manifesto or an existential crisis, it gives you room to shape not just how you work, but how your entire organization adapts to this shift.

The only wrong response is waiting for someone else to figure it out first. The conversation has already started.

Katie Parrott is a writer, editor, and content marketer focused on the intersection of technology, work, and culture. You can read more of her work in her newsletter.

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