A practical AI readiness checklist for 50–500 person teams

If you're at a 50–500 person company, you've already had at least three vendor pitches about AI this quarter. Most are noise. A few are real. Here's how to tell which is which — and what to fix on your side before any vendor can help.

Start with data. Where does your business data live? Who owns it? When was the last time it was audited for quality? If you can't answer those three questions cleanly, your AI strategy will fail no matter how good the vendor is.

Next, processes. Map the top five repeatable processes by hours-per-week. AI is good at automating these — but only if they're documented well enough that an outsider could follow them.

Then, talent. Do you have at least one engineer who can call an AI API, parse a JSON response, and ship the result to production? If not, hire one (or partner with someone) before evaluating tools.

Finally, governance. Who decides what AI you use? What's the policy on customer data going to third-party APIs? If those answers are vague, get them clear before deploying anything customer-facing.

Vendor demos are easy to evaluate once the above is done. The right ones will ask you these same questions; the wrong ones will skip them and pitch features.