Navigating AI requires close attention to FOUR of our TEN CEO Roles: Deliver Winning, Innovative, Timely Products and Services | Lead the Company Through Change and Transformation | Live Your Core Leadership Principles and Serve as Chief of Culture, Communication, and Organization

Do not be lulled by the placid race above! The AI tempest has made landfall. For tech CEOs, the window for getting ahead of this is not measured in months. It is measured in weeks. The question is no longer whether AI will reshape your company’s destiny. It will. The question is whether you as the CEO are going to steer that reshaping from the front and have the courage to move forward quickly in the face of huge uncertainty!

AI will quickly stop being novel. What is window-dressing today will be table stakes tomorrow. The question for every CEO right now is: what will your defensibility be once AI is no longer unique? That question needs an answer, and it needs one now. This is not a technology conversation. It is a leadership one. Only the CEO can drive this. How you drive it is pivotal to your company’s success.

And, please also remember that no matter where you are on the AI adoption curve model it is most important to live your core value principles and model your company’s culture drivers. Be kind, be transparent, be honest, and be brave. This change is difficult and stressful for everyone in the ecosystem you lead!

Special thanks to long-time High-Growth CEO Forum® member Gary Ambrosino for contributing his insights to this post.

Critical AI Trends

AI Fluidity
AI is becoming a fluid, ubiquitous element across all business operations rather than a standalone tool – a presence that permeates every part of a business’s workflow and the entire operational landscape.

AI as a Profitability Moat
AI must be mapped out into a program that creates a defensible moat and drives widespread profitability.

Premium Valuation through AI Story
Investing in a forward-looking AI narrative is critical for positioning a company for premium valuation.

Agentic Workflows for Productivity
Re-platforming to include agentic workflows allows for massive productivity gains and cost reduction.

Next Generation AI Architecture
Transitioning from traditional software stacks to next-generation AI architectures is required.

What Kind of CEO Are You – AI Firebrand, AI Middler, or AI Laggard?  

Your Company’s Course Will Depend on the Course You Chart!

The AI Firebrand CEO is the AI champion for the company, and everybody knows it!

  • A Player/Coach/Doer – no matter the company size and stage, the Firebrand is personally immersed in using AI tools.
  • Works alongside the team – does not just direct from above. They pull their team forward and don’t wait for their team to catch up!
  • Key executives, especially technology leaders, are required to spend weeks learning and using AI!
  • The Firebrand CEO understands how large language models (LLMs) work, and how data and LLMs interact. 
  • They know what you mean when you ask how they organize their data corpus. And they understand that the value is not in the LLM itself but in the harness you build around it.
  • AI Native: They are working to re-architecting products to be “AI Native.” Not simply to add a chatbot interface on top of an existing system.

“The key is engaging AI as a human resource.   At a minimum – you have to learn to scope a task, set goals, write prompts, skills, and behaviors just like you give an assignment to a team member. And importantly give them the set of information they should reference for the task.” — Gary Ambrosino

  • AI Firebrand CEOs are the ones investors ask to showcase their AI experience across portfolio companies and whose expertise is in high demand from their CEO peers.

Result: They are moving forward at lightning speed, figuring out how to fund and staff the technical transformations, thinking about required team and company re-organizations and staying laser focused on building customer value and true competitive moats!

 

The AI Middler CEO: The Middler CEO is making a true effort and assumes they are doing enough. And maybe they are?  Depending on their desired outcome.

  • They understand roughly what 700 million other ChatGPT users understand about interacting with AI.
  • They have connected their Google Drive to Claude and are trying some stuff.
  • The Middler encourages their team to “adopt AI somewhere somehow.”
  • They may use hiring as a proxy for progress and say to themselves, “I need to bring in someone who knows how to do this.” This response substitutes a search process for the CEO’s own immersion, and three months of recruiting puts you three months further behind your competitor who went first.
  • They look for productivity by gating new hires based on AI replacement criteria.
  • They plan to or may have added some AI positioning to the website. 
  • They assume they can “AI-decorate” a product and achieve competitive advantage from it. They think it will increase valuation and create a durable competitive moat. On all three counts, they are wrong:
    • AI decoration, placing a familiar chat interface on top of existing functionality without fundamentally rebuilding the underlying architecture, does not deliver AI-native valuations.
    • It may buy time, but it does not build defensibility. 
    • As one HGCF member put it: “decorating a product with AI may give you a temporary competitive advantage, but it will not be durable.”

Result: The Middler is not doomed. If budget constraints or investor limitations make a full product re-architecture impossible right now, getting to Middler could still be a meaningful outcome. It avoids valuation disaster. The goal for an investor-backed company that cannot yet fund a full rebuild is not to fail at being a Firebrand. It is to succeed at being a Middler.

 

The AI Laggard CEO: The Laggard makes excuses that their industry, product, or operations are not ripe for AI. 

  • They delegate whatever adoption happens to a few executives who seem to get it. There is no plan. No time set aside. No personal exploration.
  • The Laggard CEO has not identified their core defensible business advantage. This is extremely dangerous In a world where AI can replicate features quickly and where customer relationships are no longer the moat they once were.

Result: This is at your peril especially if your business is easy to replicate using AI technology, and you have not built a defensive moat. There is an extremely narrow exception – if you are in a super niche with zero competition and genuinely no credible path for AI to disrupt your market, you may be able to stay here. But that describes perhaps three percent of companies?

The Valuation Stakes Are Already Set

This is not a future scenario. The die is already being cast. Investor expectations around AI adoption are bifurcating valuations in real time. The Firebrand is commanding 10 to 20 times or more in revenue multiples. The Middler lands somewhere between one and three times. The Laggard risks getting 20 to 50 cents on the dollar.

In private equity portfolios especially, many companies avoided write-downs in early 2025. That grace period will not last another year. The CEOs who are still treating AI as a “wait and see” initiative are making a valuation decision right now, even if they do not realize it. VC funding for non-native AI companies has ground to a halt and CEOs are struggling to become breakeven asap.  Time is not on anyone’s side!

What distinguishes AI-decorated products from AI-native products matters acutely here. A chatbot layered on top of existing data retrieval is not AI in any meaningful sense that investors are rewarding. The distinction is architectural. AI-native means the product has been rebuilt from the inside out, with data, process, and decision logic encoded into AI intelligence rather than hardcoded into a fixed SaaS structure.

How to Move Forward: From Laggard or Middler to Firebrand

Step One: Immerse Yourself, No Excuses

The first move is non-negotiable. The CEO must personally use AI. Not delegate learning to a team. Not commission a report. Sit down with the tools, build something small, and try to solve a real business problem. The shift from asking your team to adopt something you have not experienced yourself to leading from personal fluency is the difference between a mandate that lands and one that does not.

The resources are everywhere and many are free. Log into Claude and ask it to create a beginner tutorial on prompt engineering with exercises. LinkedIn Learning offers comprehensive AI coursework for roughly $300 per year. There is no legitimate excuse for a college-educated CEO not to find a path into this material.

Block the time. A Saturday morning. A holiday break used as an AI sprint. If you are not willing to make this investment, the conversation with your team will never carry the weight it needs to.

“If you are a CEO that does not enjoy learning and does not want to make the investment to learn this, you should retire. Because you are done.” — Gary Ambrosino

Step Two: Understand What Your Defensible Advantage Actually Is

Once you have personal fluency, the strategic work begins. You are now in a fluid world. A SaaS product crystallizes your market knowledge into a fixed structure. AI changes that entirely. Your competitive advantage now lives in knowledge repositories, unique data, and proprietary process understanding, and only if that knowledge is encoded into AI intelligence.

This requires a genuine strategic analysis:

  • What does your company know that no one else knows?
  • What data do you have access to that is genuinely unique?
  • What process and understanding have you built that can be encoded, not just described?

These are the questions that separate the companies that will maintain valuation and a growth journey from those that will not.

Step Three: Build Courage, Set the Pace, Lead the Team, Be Decisive, Be Transparent

After personal fluency and strategic clarity comes the hardest part: being the change agent in the face of uncertainty. AI allows you to move and pivot faster than you ever could before. A product that would have taken a year to develop can be rebuilt in weeks. That speed advantage only accrues to the CEO who is willing to go first without waiting for certainty.

Once you have built something yourself, bring that experience directly to your technology leader. The conversation changes entirely when you can point to exactly what is possible and exactly what pace is acceptable. Give your engineering team a deadline, not a framework. Ask for a concrete AI strategy with owners and timelines, not a slide deck.

Then give your entire team the time and permission to experiment. If you have not already given your function leaders a defined window to develop an AI strategy for their area, set that expectation now. The culture of adoption spreads fastest when the CEO models the behavior first.

When your team sees you willing to be a beginner, willing to invest your own time, willing to look uninformed in service of getting informed, it gives the rest of the organization permission to do the same.

The Self-Assessment Every Tech CEO Needs Right Now

For tech CEOs, this is the most important set of questions on the table right now. Not where you want to be on AI. Where you actually are.

  1. Have you personally used AI tools for a real business task in the past 30 days? 
  2. Has your technology leader been given a clear mandate and a deadline? 
  3. Have your function leaders been asked to develop an AI strategy for their area? 
  4. Has your team been given structured time to experiment, not just encouraged to explore?

If the answer to any of these is no, the gap between you and the CEOs gaining the most ground is already wider than it needs to be. That gap can be closed quickly. But only if the CEO goes first, and does so quickly! 

The Question Is No Longer Whether. It Is Who Goes First.

The CEOs in our High-Growth CEO Forums® gaining the most ground on AI are not the most technical. They are the most willing: willing to block the time, willing to sit with an unfamiliar tool, willing to build something small and imperfect and learn from it.

Great CEOs do not wait to be convinced. They go find out.

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