Q2 2025 is the quarter that CEOs finally woke up to the generative AI era. It’s not that they weren’t paying attention to generative AI’s impact on organizations, or that they weren’t feeling the urgency. It’s that they finally started talking about it publicly.
Shopify CEO Tobi Lütke kicked everything off with a memo to all his employees with declarations like “using AI is now a fundamental expectation of everyone at Shopify” and “before asking for more headcount and resources, teams must demonstrate why they cannot get what they want done using AI.” Within weeks, Duolingo CEO Luis von Ahn, Box CEO Aaron Levie, Fiverr CEO Micha Kaufmann, and countless others published their own memos or somehow chimed in. The tone and details varied, but the message was the same: every CEO wanted to make it crystal clear that their company is now AI-first and there’s no going back.
Focus on enablement, not replacement
The CEOs are all saying the same thing for good reason: Like in the mobile revolution, those who embrace AI before it has matured will benefit the most.
Contrary to popular belief, organizations that are embracing AI are also heavily investing in their employees. Good leaders are clear-eyed about AI’s impact, but they are doubling down on talent, not fearmongering that AI will automate humanity away. The memos say as much:
- Duolingo is “going to support you with more training, mentorship, and tooling for AI in your function.”
- Box aims to “upskill every employee to be AI-first over time with more education and awareness.”
- Fiverr says that “it does not make sense to hire more people before we learn how to do more with what we have.”
Leadership in the AI era means ensuring the whole company is learning and leveraging AI tools together. How do you embrace AI without making your people feel disposable? You invest in them and show them how AI makes them more valuable and powerful. You emphasize that AI is a tool to augment their brilliance, not replace it, and that they are in an environment where they have the room to experiment freely and share what they learn back with everyone.
Become AI-forward, or get left behind
These CEOs are not talking about the distant future — they’re talking about the present day. I’ve seen organizations start to shift soon after a CEO has their AI enlightenment moment — that “holy shit” realization when AI’s potential suddenly clicks, and they start to ask, “Why aren’t we using this everywhere?”
But an AI epiphany isn’t enough. You have to operationalize it.
Product velocity is everything in the AI era; it’s the brutal difference between leading and becoming a footnote. Furthermore, the external battle for product supremacy is often mirrored by an internal one: getting your own people to actually use AI. Forget the narrative that employees are scared AI will replace them. The stark reality? Most still haven’t even meaningfully tried ChatGPT. Not because they’re Luddites, but because no one showed them why it matters to them.
Companies keep tossing AI tools over the fence, then act surprised when usage numbers quickly dwindle. That’s not enablement. It’s neglect.
Work toward AI fluency
I hear it constantly: “Some are curious, others are hesitant. We don’t know how to move the needle.” You can’t brute-force AI fluency, but you absolutely can design for it.
Here are some tips to quickly turn AI skeptics into AI advocates:
- Build a culture of failure and learning: Make it safe to try, stumble, and share the bloody-nosed lessons. Innovation in AI isn’t a clean process.
- Track performance, not just clicks: focus on AI’s impact on business outcomes (faster turnarounds, smarter decisions, and resources saved), not just tool logins.
- Repeat that AI tools are here to help, not replace: You want your employees saying, “My company invests in me” and “AI makes me better.”
Existing companies need to play with AI tools, get enlightened about AI’s potential, and ruthlessly embed AI across teams and processes. Once your team understands AI’s power, they’ll go all in. Don’t let the morass of large organizations stop you with analysis paralysis or death by committee.
New startups can be AI-native from day one. Don’t just offer AI to your customers, infuse AI into every business function, since you already have conviction in the technology. Give all your employees Claude, Granola, and Cursor, not just Gmail, Notion, and Slack.
Final thoughts
AI removes the busy work, leaving humans to do what they’re best at: soft skills, storytelling, and strategy. AI fluency is a killer competitive advantage now, but in a few years it will be the baseline, like how today, everyone has an email address.
Most companies miss this, treating AI as an add-on, not the OS. To be a leader in the AI era means that you stop asking, “Where can we try AI?” and start demanding, “Where can we no longer afford not to use AI?”
The time for cautious exploration is over. The AI era demands bold bets, a relentless focus on enablement, and the courage to weave AI into the very soul of your operations.
