Who Should Lead Your AI Transformation?

Author

Charlene Li
September 30, 2025

Let me start with a question: Who should be leading your AI efforts?

Most companies get this one wrong. 

In our forthcoming book, Winning With AI: The 90-Day Blueprint for Success, my colleague Katia Walsh and I have built a robust roadmap for organizations ready to take the next step with AI and shared how to make the most of the investment.

During our research and writing, one thing became crystal clear: regardless of how motivated and excited a company is to use AI, implementation can’t succeed without dedicated AI leadership. 

Today, I’ll share our roadmap for finding the ideal AI leader, and how to leverage their work for successful AI launches, scaling, and value delivery.cause the technology doesn't work. It's because of how these pilots are constructed.

The Default That Doesn't Work

Most companies default to making AI the responsibility of their CIO. It feels logical, right? After all, AI is technology, and the CIO manages technology.

But here's the uncomfortable truth: traditional IT leaders focus on keeping systems running, managing risk, and operating as internal service providers. They think in terms of system deployment and maintenance—not organizational transformation or rapid value creation.

When AI sits under traditional IT leadership, it joins the typical IT machine of cautious, years-long rollouts measured by uptime, not business outcomes. That's why your AI pilots aren't scaling.

What AI Leadership Actually Requires

Leading AI transformation demands someone who can operate simultaneously as a change agent, strategist, and business value integrator. Someone who can move seamlessly between tech, business, and driving value. Your AI leader must be:

▶️ A business leader with entrepreneurial pragmatism.
▶️ A problem solver who scales solutions beyond pilots.
▶️ A proven change agent who has driven transformation.
▶️ A value creation driver focused on measurable business results.
▶️ Technically credible enough to evaluate opportunities and guide teams.

This isn't your traditional IT executive. And it's not a pure technologist either.

The Moderna Model: Thinking Outside the Box

AI requires creative thinking, and companies that think outside the box when it comes to AI leadership are reaping the benefits. For example, Moderna put AI—along with all of IT—under their Chief Human Resources Officer.

Unusual? Absolutely. But it strikes at a crucial insight: the person leading AI must understand both business strategy and technology, and be positioned to drive cross-functional change.

Moderna recognized that AI transformation is fundamentally about people, processes, and organizational change. Their CHRO had the business credibility, change management expertise, and CEO access to drive enterprise-wide adoption.

Your Three Options (And Why Two Don't Work)

1️⃣ Default to your current CIO 

This feels like the most obvious option but it runs the risk of keeping your AI initiatives in a stagnation zone. This approach fails unless you have that rare next-generation technology leader who thinks like a business transformation agent. Be honest with yourself: does your CIO fit that profile?

2️⃣ Hire a parallel Chief AI Officer 

This preserves stability in core IT functions but can create territorial friction between two technology leaders, resulting in organizational confusion and coordination overhead. I've seen too many talented CAIOs fail because they're fighting structural battles instead of driving value.

3️⃣ Bring in a next-generation technology leader 

This is someone who can replace or work above your traditional IT executive in order to drive both infrastructure and AI transformation. This eliminates silos and ensures unified accountability for technology-driven value creation.

An organizational change of this scale needs to be powered by a courageous CEO who’s not afraid to disrupt the status quo for a more efficient, effective future.

The One Non-Negotiable: Accountability

Choosing your AI leader is no small feat. Whether you go traditional or choose to shake things up, one thing remains true:

You need one person who wakes up every morning 100% accountable for creating value with AI across your organization.

Not shared responsibility. Not collaborative oversight. Not "we're all responsible."

One leader with enterprise-wide authority, direct CEO access, and the power to break down silos.

Making the Hard Choice

This decision can't wait while you analyze every angle. Each week without dedicated, competent AI leadership costs your organization competitive advantage.

Ask yourself:

🪢 Can you afford the coordination complexity of parallel technology leadership?

📊 Can you maintain the status quo while competitors are disrupting your business with AI?

🚀 Does your current technology leader have the change agent ability and business value focus to drive AI transformation?

The companies winning with AI establish dedicated leadership accountability early. They don't let organizational convenience override strategic necessity.

Your AI leadership decision sets the foundation for everything that follows. Choose quickly, choose decisively, and give your leader the authority they need to succeed.

Because in AI transformation, half-measures guarantee mediocrity.

💬 Your Turn

Who is leading AI at your organization? Does that person have both the technical credibility and business transformation experience to drive enterprise-wide change?

What changes would you like to see in the AI leadership at your organization?

What I Can’t Stop Talking About

  • Sick of AI pilots failing before they even take off? You’re not alone. Companies are investing in pilots without committing to scaling them, and it’s a growing problem. 95% of AI pilots fail, but the 5% that succeed and drive value have some key elements in common. 

  • AI is leveling the playing field for small companies. Capabilities that were once exclusive to enterprise organizations are now available to SMBs, thanks to AI. It’s making it possible for good ideas to gain market share and compete at a higher level. It’s one of many reasons to feel optimistic about AI. 

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