How to use AI in your business (Madison, Wisconsin)

I’m Jake Roder. I live in Madison, Wisconsin, and I spend my time on Microsoft business applications and on helping small and mid-sized companies get real work out of AI.

If you searched something like this, you have probably already found a hundred articles telling you to leverage AI, and none of them told you what to do on Monday morning. So here is what I actually tell people.

Start with a task, not a tool

The most common mistake I see is picking a tool first and then hunting for something to point it at. That gets you a subscription and a demo nobody uses.

Go the other way. Find a task somebody on your team does every week that is mostly reading, writing, checking, or reformatting. Those are the tasks that pay off first, because the work is repetitive but still needs judgment, which is exactly what these tools are good at.

Good candidates usually sound like: “someone spends a day a month building that report,” or “we rewrite the same proposal every time,” or “we find the errors after the customer does.”

Where it tends to pay off first

Three patterns come up over and over with companies your size:

• Document work. Proposals, statements of work, summaries, anything where the format matters and the content changes. I wrote up how to make this repeatable in getting consistent, on-brand documents out of AI every time.
• Checking data nobody has time to check. Reconciliations, master data, lists that quietly drift out of sync. Here is a real example: catching data inconsistencies with Claude Cowork.
• Reporting and analysis. Not replacing your BI tool, but getting to the answer faster. I use it constantly alongside Power BI, for instance when calculating utilization from Dynamics 365.

None of these are moonshots. They are all a few hours of somebody’s week, given back.

What goes wrong

• Buying licenses before deciding what they are for. Seats are cheap to buy and expensive to waste.
• No rules about company data. Decide what can and cannot go into these tools before your team decides for you.
• Treating output as finished. The useful posture is that AI produces a solid first draft that a person still owns.
• Starting with the hardest thing you do. Start with the most repetitive thing you do.

What it costs

For a small or mid-sized company this should not be a six figure program. My AI practice, Tapestries Group, works in fixed-price, scoped engagements rather than open-ended hourly work, precisely because “how much will this cost” is the question that stalls most of these projects. Deployment, guardrails, training, and building the workflows are all separate, scoped pieces, so you can start small and stop whenever it stops being worth it.

If you are in Madison

I am local, so an actual conversation is easy, and I am happy to be useful even if you never hire me. If you want to think out loud about where AI fits in your business, book some time below. If you would rather just read, most of what I have written on this is in the AI section or on my start here page.

Hope this helps.