Hiring

Roofing Contractors in Madison: Questions to Ask Before You Hire

By Madison Roof Repairs · September 10, 2026 · 5 min read

Madison has a lot of roofers. After a hailstorm it has three times as many, and most of the extras will be gone by Labor Day. Sorting the good local companies from the rest takes about twenty minutes and a handful of questions. Here they are, with the answers you should hear.

"What's your Wisconsin credential, and who's your qualifier?"

Wisconsin doesn't have a roofing license by name. What it has is a Dwelling Contractor certification, issued by the Department of Safety and Professional Services to a business that has shown proof of liability insurance or a bond, and a Dwelling Contractor Qualifier credential held by a person in that business who has passed the state's exam on the Uniform Dwelling Code and keeps up continuing education. Without both, a company cannot legally pull a building permit for work on a one- or two-family home in Wisconsin, and Madison and every suburb require a permit for a re-roof.

Any legitimate roofing company can name its qualifier and show both credentials. You can verify them yourself on the DSPS credential lookup in a minute: search the business name and the qualifier's name, and check the expiry dates. A company that can't answer this question, or says "we don't need that for roofing," is telling you what you need to know.

"Send me your insurance certificates"

Two documents: general liability and workers' compensation. Ask for the certificates to come directly from the insurance agent, with your name as certificate holder, not as a photo of a piece of paper. A roofer whose crew member falls off your roof without workers' comp becomes a claim against your homeowners policy. This is the question that separates roofing contractors Madison homeowners regret from the ones they recommend.

"Where's your office?"

A local address you can drive to. A phone number with a 608 area code that someone answers. Trucks with a company name, not magnetic signs. None of this guarantees quality, but it guarantees someone to call in 2029 when the valley leaks.

"Will you go in my attic?"

A roofer who quotes a replacement from a satellite measurement and a walk around the yard hasn't seen the decking, the ventilation, the frost on the nail tips, or whether the ice-and-water shield from the last roof actually exists. The best roofers in Madison go into the attic on every estimate. If they won't, you'll find out what they missed on invoice day.

"What exactly is in the quote?"

Get it in writing, itemized. For a replacement, look for:

A quote missing three of these isn't cheaper. It's incomplete.

"What's the workmanship warranty, and who honors it?"

The manufacturer warrants the shingle. The roofer warrants the installation, which is where most leaks come from. Ask how many years, get it in writing, and ask what happens if the company closes. A storm chaser's ten-year workmanship warranty expires when the truck leaves the county.

"How do you handle my deductible?"

The only right answer is "you pay it." Wisconsin law prohibits a contractor from paying, waiving or rebating an insurance deductible, and a company that offers to is planning to pad the invoice to cover it — which is insurance fraud, on a claim with your name on it. Wisconsin also gives you three business days to cancel a storm-repair contract after your insurer denies the claim. A contractor who explains those rules without being asked is one to keep.

"Can I see a job you did five years ago?"

Not a fresh one. Anyone can make a roof look good the week it's finished. Ask for a few addresses of roofs done years ago and drive past them. Look at the ridge line, the valleys, whether the flashing at the chimney is still tight.

The tells

Things that end the conversation:

• Knocked on your door the morning after a storm
• Wants a large deposit today, or "today-only" pricing
• Offers to waive the deductible
• Won't name a qualifier or produce insurance certificates
• Quotes from the driveway in ten minutes
• No permit in the price, or "you can pull it yourself"

What the good ones sound like

A written scope after a roof-and-attic inspection, with photos. Prices in line with the cost page. A real address. A qualifier they'll name. A willingness to say "this roof has three more winters" when it does. That's the whole test.

If you have storm damage, the hail and wind damage page covers the claim process, and the about page explains how we handle every one of the questions above.