Compare Policy Documents in Minutes with AI

Grant Calloway

Welcome to AI for Small Business. I'm Grant Calloway. On the exchange floor, the tape came at you faster than any human could read it. The edge was never reading faster. The edge was knowing what to ignore, so you had a clear head for the one print that mattered. Now picture an independent insurance agent on a Tuesday afternoon. A hundred page renewal is on one side of the desk, last year's policy is on the other, and a client is waiting on a call. That agent is acting as a human ticker reader. Today, we fix that for about twenty dollars a month.

Grant Calloway

Here's the problem. A commercial policy isn't one document. It's declarations, endorsements, coverage schedules, all of it dense and written by lawyers for lawyers. When renewal comes, somebody has to answer one question: what changed? Did a sub limit shrink? Did a new exclusion sneak in? Did the deductible jump? Historically, that meant reading page by page, and it could eat a day or two. One industry guide, published by an AI phone vendor called Sonant, estimates licensed agents spend more than two and a half hours a day on routine administrative work. That's a vendor's estimate, so take it with a grain of salt. But anyone who's worked in an agency is nodding right now.

Grant Calloway

Now let's zoom out, because the data here is unusually solid. The JPMorgan Chase Institute published a report in April 2026 using de-identified Chase Business Banking transaction data, covering 4.6 million small businesses from 2019 through 2025. It doesn't ask people what they plan to do. It tracks who actually pays for AI. The 2025 group of new firms reached ten percent adoption in about six months. The 2019 group took seventy seven months, more than six years. That's nearly thirteen times faster. And the entry price collapsed. The median starting spend fell from roughly fifty dollars a month in 2019 to about twenty to thirty dollars in 2024 and 2025. One caveat from the researchers: they only count paid tools, so real usage is probably higher.

Grant Calloway

Two more numbers matter for service firms. Professional services sit at about thirty percent adoption, while construction sits under nine. And businesses with employees adopt at nearly twice the rate of sole proprietors, 26.1 percent to 15.3 percent. That gap holds even among low revenue shops. So the barrier isn't money. A twenty dollar tool is cheaper than the coffee budget. The barrier is hands and bandwidth. It's like owning a tractor but having nobody free to drive it. So let's look at someone who found a driver.

Grant Calloway

Jeff Brehmer is president of Smith Davis Insurance, an independent agency with three offices: Council Bluffs and Logan in Iowa, and Papillion in Nebraska. He's up against big consolidators and direct to consumer platforms that are investing heavily in AI. He also co leads an AI Working Group inside the ISU Steadfast network, alongside Todd Hufford, the chief operating officer of Conner Insurance. It's a group of agency leaders who test tools and share what works and what's overhyped. Here's what Brehmer told ISU Steadfast about document analysis and policy reviews. Quote: "What used to take me two days now takes 10 minutes." End quote. Then the part I love. Quote: "It's amazing how much quicker you can get 90% of the way there, versus having to put together everything manually." End quote.

Grant Calloway

Notice the words ninety percent. He isn't claiming the machine finishes the job. The machine gets the first draft of the comparison. The human does the last ten percent, the judgment part, which is the part clients pay for. This episode is brought to you by Jellypod. If you've ever wished you could put out a regular podcast without hiring a production crew, Jellypod creates AI podcasts for your business on autopilot. Think of it as a studio that never clocks out. Find out more at jellypod.com.

Grant Calloway

Back to the agencies. Todd Hufford described a project his team is still testing, what he calls a digital service agent. It would handle routine requests, like a vehicle change, then hand a complete packet to a live account manager to review. His expectation is that it will save fifteen to twenty minutes or more per transaction. Notice it's a goal, not a finished result. And Steven Tuften, who leads AI and emerging technology at Steadfast Group, gave the rule for all of this. Quote: "When someone's just experienced a loss, they don't want to talk to a chatbot. They want to speak with a real person." End quote. Machine on the paperwork, human on the person. That's the whole philosophy.

Grant Calloway

One more data point, with a flag on it. An eleven person agency in North Carolina, O'Connor Insurance Associates, reports saving more than fifty eight hours a month with an AI phone answering tool. That figure comes from the vendor that sold it, so treat it as a claim, not an audit. But the direction matches everything else. Take the repetitive friction away from licensed people, and they get their days back.

Grant Calloway

This week's tool is Claude, from Anthropic. The Pro plan runs twenty dollars a month per user, and there's a Team plan if you want several people on it. Its strength here is that it can take in very long documents, so you can hand it two big PDFs at once and ask it to compare them. It's best for any firm that drowns in paperwork: insurance agencies, yes, but also contractors weighing two subcontractor proposals, or an accountant looking at a revised engagement letter. ChatGPT Plus can do a similar job, so use whichever you already pay for.

Grant Calloway

Two guardrails before you start. First, these tools can sound confident and still be wrong. A Gallagher survey this year found more than half of business leaders worry more about AI errors than about legal risks. So you check the work. Second, read how your tool handles the data you upload, and don't paste in anything sensitive until you're comfortable with the answer. Set a simple rule for your team on what goes in and what stays out.

Grant Calloway

Now, your challenge. It takes under an hour. Step one, five minutes: find two long documents you've been putting off comparing. An expiring business liability policy and its renewal. Two vendor quotes. A contract and its revision. Step two, five minutes: upload both into Claude or ChatGPT Plus. Step three, ten minutes: paste in this prompt. "Act as a professional risk consultant. Analyze Document A, the existing one, and Document B, the proposed one. Build a table with these columns: Coverage or Feature, Document A Terms, Document B Terms, Difference, and Risk Flag. Highlight any exclusions, higher deductibles, reduced limits, or restrictive conditions in Document B that were not in Document A." Step four, fifteen minutes: take every flagged difference and check it against the original pages. Confirm it's real, and notice what's missing too.

Grant Calloway

When you finish, look at the clock. A job that used to burn half a workday should be mostly done. That's the point. The biggest takeaway today is simple. Independent agents and service firms are Main Street's risk specialists. They shouldn't spend billable daylight acting like human scanners. Let the twenty dollar machine do the heavy lifting in ten minutes, and spend the rest of the day looking the customer in the eye. That's where the real edge has always been. Thanks for listening, and go run that comparison today.