Building an AI Strategy in a Mid-Market Company: The CEO’s Guide (part 1 of 4)
AI for Mid-Market Leaders Series – Part 1 of 4
First, let’s state the obvious: we’re all getting AI fatigue. Every headline, panel discussion, and keynote feels like another breathless take on how AI will “change everything forever.”
This is not one of those articles. This is about something practical and very real for mid-market companies.
AI strategy must be built differently depending on the size and structure of your organization – and in mid-market businesses, the CEO has to lead that effort. And the main reason is that the operating realities are different.
How Enterprise AI Strategy Typically Begins
Large corporations generally begin major strategic initiatives, including AI, the way that makes sense for them:
The Board requests a perspective.
The CEO turns to the C-suite.
The organization activates the right structure:
cross-functional working groups
analysts
program managers
finance and risk teams
internal consultants
They develop a well-researched, well-governed approach.
This is appropriate for enterprise-scale organizations. They have multiple layers of leadership, dedicated strategy teams, and the ability to reassign people temporarily, among other structural supports. Nothing wrong with this. It’s designed for complexity.
But that same structure is exactly why mid-market companies must take a different path.
Mid-Market Companies Have Different Strengths and Constraints
Mid-market companies (typically $5M–$100M revenue) don’t have surplus strategic bandwidth sitting on the bench. If you take two or three key people away for six weeks to “explore AI,” the business feels it.
Your organizational reality is:
Tighter leadership teams
Leaner management layers
High interdependence
Limited unallocated capacity
Less room for exploration without impact
Faster decision cycles — when aligned
These are not disadvantages. In fact, they can be huge advantages.
But they do mean that you cannot simply transplant the “large enterprise” AI playbook. So where does AI strategy start in a mid-market business?
With the CEO; and with rapid alignment at the leadership table.
Why the Mid-Market CEO’s Role Is Central (and Not Delegate-able)
This isn’t about hierarchy. It’s about clarity. AI touches:
Operations
Customer service
Finance
HR
Sales
Process design
Project delivery
Decision-making
Communications
Because AI affects how the whole business operates, only the CEO has the vantage point to frame why AI matters, set direction, keep priorities focused and ensure leaders are aligned (and stay aligned).
So, What Should a CEO Do Next?
Here’s the first concrete step in your mid-market AI journey:
CEO Action #1:
Schedule a 60–90 minute leadership alignment session to answer one question:
“If AI becomes a core capability for us, what do we need to align on before we start experimenting?”
Don’t worry about AI tools yet. Don’t worry about pilots. Start with clarity, then build focus, and only then design action.
In our upcoming newsletter, we’ll share more details about a meeting agenda you can use, as well as a template for building your AI Blueprint for Action, so you can run this session confidently and effectively.
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