Hiring

Roofing Contractors in Chesapeake: Questions to Ask First

By Chesapeake Roofing Pros · September 11, 2026 · 5 min read

Every storm season, roofing in Chesapeake fills up with companies that didn't exist in the spring. Some are good crews who move with the weather. Many are a sales office, a subcontracted crew that changes every week, and a phone number that stops working in eighteen months. The questions below take about ten minutes and separate the two.

1. What's your Virginia contractor license number and class?

Virginia requires anyone contracting for roofing work over $1,000 to hold a license from the Board for Contractors, part of the Department of Professional and Occupational Regulation (DPOR). There are three classes: Class C for jobs under $10,000, Class B up to $120,000, and Class A unlimited. For house work the license should carry the RBC (residential building contractor) specialty.

Get the number and look it up at dpor.virginia.gov. Check that the name matches the company on the contract, the class covers the size of your job (a $16,000 replacement needs Class B or A), and it hasn't expired. A company working under someone else's license or "in the process of getting one" is unlicensed, and Virginia's Contractor Transaction Recovery Fund, which can reimburse homeowners harmed by a licensed contractor, won't help you.

2. Can you send your insurance certificates before the crew arrives?

Two documents: general liability and workers' compensation. Ask for the certificates to be sent directly from the insurer's agent, not photocopied. If a roofer with no workers' comp has a crew member fall off your roof in Deep Creek, the claim can land on your homeowners policy.

3. Who's actually on my roof?

A lot of Hampton Roads roofing is subcontracted. That's not automatically bad, but you want to know whether the crew works for the company you're hiring or was found that morning, and whether the same foreman will be there both days. Ask who supervises the job and who you call if something looks wrong at 2 p.m.

4. What shingle, what wind rating, how many nails?

A good answer names a product line and its ASTM D7158 wind class — Class H is 150 mph, Class F is 110 — and says six nails per shingle. Chesapeake's design wind speed under the Virginia code is high enough that four-nail installation on a standard shingle is a warranty problem and a storm problem. If the answer is "30-year shingles" with no name, keep asking.

5. What's under the shingles?

Synthetic underlayment or felt? Ice-and-water membrane, and where — valleys, penetrations, eaves? New flashing or reused? Ridge vent? Any quote should say. The cheap quote in a stack of three is usually the one reusing the flashing and putting felt on the deck.

6. Is the permit included?

The City of Chesapeake requires a building permit for a tear-off and replacement, and the inspector wants to see the deck and underlayment before shingles go on. A roofer who suggests skipping it to save you $150 is telling you how they treat the parts you can't see.

7. What happens if you find bad decking?

The right answer is a per-sheet price, usually $90–$150, written into the contract, with photos of every sheet replaced. "We'll deal with it if we find it" means a surprise on the invoice.

8. What's the warranty, and who honors it?

Two separate things. The manufacturer's warranty covers the shingles — often 25 years to lifetime on materials, and longer if the company is certified to install a full system. The workmanship warranty covers the installation, and it's only as good as the company still being here. Ask how long they've had the same phone number and where the office is. A roofer with a Chesapeake address and a truck you've seen on Battlefield Boulevard for a few years is a different bet from a P.O. box.

9. Will you look at the attic?

The best roofers in Chesapeake go in the attic on every estimate. It's where the leak trail is, where the ventilation problem shows, and where you can see whether the decking is solid. A company that quotes from a satellite measurement and never opens the hatch is guessing, and you'll pay for the guess.

Red flags that end the conversation

• Knocks on your door after a storm and offers a "free roof" by covering your deductible. That's insurance fraud in Virginia.
• Wants a large deposit up front. Materials are delivered the morning of the job; a deposit of more than about 10–30% has no reason to exist.
• Pressure to sign today for a price that disappears tomorrow.
• Asks you to sign an assignment of benefits that gives them control of your insurance claim.
• Out-of-state plates and a magnetic door sign.

What a good estimate looks like

One or two pages. Materials by name. Every layer listed. Permit and cleanup included. A per-sheet decking price. Warranty terms in years. Good for 30 days. Ours are on the roof replacement page in outline, and the about page has the license rule in full. Get two or three of them and compare line by line — our post on reading a roofing quote shows what to look for.