AI implementation roadmap: a 90-day plan for mid-market companies

90 days is the right horizon

Six months is too long — strategy decays. Thirty days is too short — nothing real ships. Ninety days lets you discover, pilot, and ship one production use case while leadership keeps their attention on it.

The plan

Weeks 1–2: Discovery + audit

• Interview 8–12 people across product, eng, ops, finance, and support. Cheap insurance against building the wrong thing.
• Audit data accessibility: what lives where, what's stale, what's siloed.
• Score 30 use cases against impact / feasibility / data readiness.
• End of week 2: a ranked backlog and one pilot candidate that's ready to scope.

Weeks 3–4: Pilot scope + SOW

• Tight scope for the pilot — one workflow, one team, one measurable outcome.
• Define success metrics upfront. "We'll know it worked if X moves Y in 60 days."
• Build-vs-buy on the model layer. Default: hosted API. Don't reach for fine-tuning yet.
• Sign-off from the pilot owner and budget owner before any code lands.

Weeks 5–10: Build

• Working code in week 5. If you don't have something to demo by end of week 5, the scope was wrong.
• Weekly demos to the pilot team. Not the leadership team — the pilot team.
• Eval suite from day one. Twenty test cases per use case, run weekly.
• Bi-weekly retros. Catch direction changes early when they're cheap.

Weeks 11–12: Ship + measure

• Production deploy to the pilot team. Real users, real tickets, real data.
• Daily readout for the first week. Catch regressions in hours, not days.
• Measure against the success metrics from week 4. Honest read-out at week 12.

Week 12+: Decide

• The pilot succeeded? Pick the next two use cases and start over.
• The pilot didn't? Honest postmortem. Was it the model, the data, the workflow, or the framing?

What to NOT do in the first 90 days

• Don't build a platform. Build a use case. Platforms are what you wish you'd built after three use cases — not before.
• Don't fine-tune anything. Prompts + RAG covers 85% of the value with a 10x faster iteration loop.
• Don't try to centralize all AI procurement in week 1. You'll spend the 90 days writing a policy doc and shipping nothing.
• Don't try to govern what you haven't built yet. Governance comes after you've seen what production AI actually does.

What this costs

For a mid-market company, plan on $40K–$120K for the pilot (depends on use case complexity). The strategy phase (weeks 1–4) can be $15K–$30K standalone if you want to scope before you commit to the build.

If you don't have the budget for both, do the strategy phase only. A 30-page report and a ranked backlog is worth more than a half-built agent.