Building an AI Roadmap: Strategic and Agile by Design

Scott Snowden
Scott Snowden
Business & Technology Strategy
Write to Scott

AI adoption is not a one-time initiative — it’s a journey. Success depends less on rigid long-term plans and more on cultivating a posture of strategic agility. At Flywheel, we emphasize building a roadmap that balances long-term ambition with the ability to adapt, flex, and refine as new developments and insights emerge.

Strategy Meets Agility

In his keynote at the Flywheel Digital Momentum Summit, Scott Brinker highlighted that the key to your AI competitive advantage is your organization’s capacity to be just a little more strategic and agile than your competitors:

  • Strategic: Set a clear direction and ambition. Know what outcomes you want AI to support, whether that’s efficiency, personalization, or innovation.

  • Agile: Remain iterative and flexible. Adjust based on real-world results, new technologies, and shifting business needs.

1:59 | Surviving Tech Changes with Scott Brinker

Watch the whole keynote: Digital Momentum Summit 2025 | Keynote: The AI Driven Future of Martech.

Keeping Your Eye on the Prize

Think of the roadmap as a journey. The destination is important, but the real focus is progress. You may not know every detail of where you’ll arrive, but the goal is to get into the right neighbourhood — aligned with your long-term ambition. The path may be circuitous, with detours and adjustments along the way, but each step should be intentional and directed toward the larger vision.

A Roadmap That Evolves

Rather than locking into a rigid, long-term plan, we advocate for a framework for progress:

  • Establish your long-term ambition — the vision of where AI can take your organization.

  • Break the journey into incremental steps and milestones.

  • Continually assess and refine based on outcomes and insights.

This approach ensures you’re always advancing without being confined by yesterday’s assumptions.

The Role of a Maturity Model

Every organization’s journey is different. That’s why a maturity model must be yours, not a borrowed template. The right model should:

  • Reflect your organization’s unique priorities and challenges.

  • Provide clarity and alignment across teams.

  • Serve as a living guide that evolves as your AI capabilities grow.

Using inspiration from industry models is fine, but the real power lies in shaping a roadmap that truly fits your context.

Build YOUR Model

We help clients build AI roadmaps that are both ambitious and adaptable. By combining strategic foresight with iterative execution, we enable organizations to move forward with confidence, keeping their eyes on the prize while working step by step toward their goals.

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