Vibe CEO-ing

Using AI to vibe with the entire organization

AI Is Transforming Executive Connection

Gone are the days of detached leadership. AI trends like vibe coding (not just for code, as we'll see below!) are empowering executives to bridge the gap between strategy and operations. Tools are emerging that enable leaders to connect and interact more deeply with every department, fostering a new era of informed, empathetic, effective and fast decision-making.

My Journey from Web Developer to "Vibe Coding" CEO

Twenty years ago, I was a web developer. As I transitioned into executive roles, I've always made it a priority to stay close enough to technology to maintain a conceptual understanding and ensure I could ask meaningful questions about tradeoffs between strategy and technical decisions.

But as companies scale, CEOs can't stay plugged into all parts of the organization. We have to shuttle from selling to fundraising, team building, culture building, customer relationships and many other priorities. That distance can create real challenges in the CEO's ability to maintain enough context to have a pulse on– and make contributions to– all parts of the organization, especially the parts that aren't the CEO's strengths (or, let's be honest, areas of interest). This distance can get especially expensive around making strategic decisions without fully understanding or accounting for technical implications, especially when there's a high level of uncertainty.

I'm seeing how "vibe coding" can have a broader application to help resolve these issues across the organization. I'm starting to describe this as "Vibe CEO-ing."

Let's start by exploring what vibe coding is, and what it unlocks for executives.

What Vibe Coding Unlocks

Vibe coding has fundamentally changed how I connect with our product, engineering team, and users. With AI-assisted IDEs like Cursor and Windsurf, I can now do rapid prototyping with users and bring these learnings back to our engineering team with tangible Github pull requests they can evaluate.

This is a leap past the whiteboard, Excalidraw, and Figma prototyping I was doing before. It creates tangible, functional artifacts rather than just static representations of an idea. And it's fast.

I've been rapid prototyping with both Cursor and Windsurf extensively. If you're not familiar with the term "vibe coding," it's basically what it sounds like – coding by chatting with an AI coding assistant to tell it what you want done, and then managing it along the way. It's definitely not perfect – here are a few screenshots of my interactions with the Cursor IDE:

What's fascinating is how these tools complement each other. Cursor is much more polished, while Windsurf tends to be more thoughtful and communicative about what's happening in the codebase. I find myself ping-ponging between them, using each for different perspectives on solving problems. When one gets stuck down a rabbit hole, the other can sometimes pull me out – similar to how you might rely on different team members to get different perspectives.

Since I don't often write production code, I consider myself a "hard core vibe coder" – I'm not reviewing every line of code the AI writes. Instead, I'm focused on the concept, the functionality, and the user experience. I'm building things just well enough to communicate the idea effectively and get real feedback from users.

Why Vibe Code as an Executive?

For executives with any level of technical background, vibe coding creates several transformative opportunities:

1. Direct User Connection: Instead of hearing about user needs through layers of interpretation, you can rapidly prototype solutions based on direct user feedback. This creates a tight feedback loop that keeps you connected to what actually matters.
2. Engineering Empathy: When you're in the codebase, even guided by AI, you develop a much deeper appreciation for the challenges your engineering team faces. CEOs who understand a company's codebase well enough to participate in technical tradeoffs and strategic technical choices are rare.
3. Accelerated Learning: You can explore technical concepts quickly, experiment with different approaches, and develop a more intuitive understanding of your product's architecture.
4. Bridging Communication Gaps: Having a functional prototype dramatically changes the conversation with your technical teams. Instead of abstract discussions, you have something concrete to react to and improve upon.

The result is magical: better alignment, faster innovation, and more informed decision-making. Your technical teams will appreciate your improved understanding, and your users will benefit from solutions that more directly address their needs.

But I'd say the biggest reason to Vibe code is to help you see how you can use similar AI-assist patterns to move beyond the code base.

From Vibe Coding to Vibe CEO-ing

Here's where I'm seeing an even bigger opportunity emerge. The principles that make vibe coding so valuable for connecting with product and engineering can be applied across the entire organization, using tools like Storytell.

Just as AI-assisted IDEs help bridge the gap between CEOs and code, tools that help CEOs connect with unstructured data across the organization can create similar bridges to every department. This broader application is what I mean by "Vibe CEO-ing."

As a CEO, you're constantly dealing with information from legal, finance, marketing, sales, customer success, and more. Each domain has its own language, conventions, and nuances that take years to master. With tools that help us navigate unstructured data, executives can:

1. Analyze deal flow and believability of quarterly targets: Sellers love to be optimistic – it's often built into their DNA. But how realistic is it that you'll really beat the quarter? What if you had easier ways of inspecting deals and providing executive air cover?
2. Quickly ramp up on contracts and other legal documents: I remember in a past startup when we did our first 50+ page enterprise MSA. I would've loved to have the ability I have now to quickly understand the implications of contract terms and provide meaningful input without being an attorney.
3. Dig into the numbers with marketing: Review campaign materials with a deeper understanding of strategy and positioning, offer valuable feedback – and ask probing questions – that go beyond surface-level reactions.
4. Understand customer trends and patterns: Analyze patterns in customer feedback across thousands of interactions, identifying systemic issues that might otherwise remain hidden. Understanding a quarter earlier than you otherwise would that a big customer is at risk of churn is almost priceless.
5. Enhance finance: Better understand the implications of financial models and projections, asking more informed questions about assumptions and outcomes so you can better plan.
6. Rinse and repeat the above for every department.

In each case, the goal isn't to replace domain experts – it's to engage with them more meaningfully as CEO. It's about closing the gap between executive vision and departmental execution, just as vibe coding does with engineering.

The Future of Connected Leadership

What intrigues me most about these developments is how they're changing the fundamental nature of executive leadership. The old model of the CEO as a distant figure who receives filtered information through layers of management is becoming obsolete.

Instead, we're seeing the emergence of connected executives who can rapidly engage with any part of their organization, understand the core issues, and provide meaningful guidance – all while respecting the deep expertise of their team members.

Whether it's through vibe coding with engineering or applying similar principles across the organization, the result is the same: more informed decisions, better alignment, and ultimately, better outcomes for customers.

Vibe CEO-ing is for executives who want to stay connected as their organizations scale. Start with the areas where you have some background knowledge, use AI tools to extend your capabilities, and focus on understanding and communication rather than trying to become an expert in everything. The future belongs to leaders who can maintain meaningful connections across their entire organization while scaling their impact.

What's your experience as a connected executive? I'd love to hear your thoughts and approaches.

And one more thing

I "Vibe-CEO'd" this piece using Storytell. I wrote a first draft, then asked Storytell to improve it based on everything it knows about me. Storytell also helped me improve the prompt itself, below. Here's the full thread of my interaction with Storytell around this piece.