Checking Out a Roofing Contractor in Brooklyn: 5 Key Things

Most Brooklyn homeowners pick their roofer based on who sounds professional on the phone and has decent Google reviews. Then the first heavy rain hits. Water’s dripping through the ceiling, the warranty turns out to be “verbal,” and the contractor who promised everything suddenly isn’t answering calls. I spent years investigating these exact disasters as an insurance adjuster-crawling through attics, reading contracts that weren’t worth the paper they were printed on, and watching homeowners lose thousands because they didn’t know what proof to demand upfront. The problem isn’t that people choose bad contractors; it’s that they don’t know how to check out a roofing contractor using hard documentation before the deposit clears.
When you’re evaluating a roofer, you’re not looking for someone who makes you feel comfortable. You’re building a verification file. Before you discuss timeline or color samples, you need to see their license, insurance certificates, permit history, and written scope-and you need to know exactly what those documents should say. Everything else is theater.

1. Verify Their License and Business Registration (In Writing)

I responded to a claim in Park Slope three years ago-beautiful brownstone, complete roof replacement done eight months earlier, now leaking at every valley and chimney. The homeowner handed me a business card and some receipts. No license number. No registered business entity. The “contractor” turned out to be a guy with a truck who hired day laborers and disappeared after the final payment. The insurance company denied the claim because there was no licensed professional involved, and the homeowner spent $23,000 out of pocket to fix everything.
In New York City, roofing contractors need a Home Improvement Contractor (HIC) license issued by the Department of Consumer and Worker Protection. This isn’t optional or negotiable-it’s the law for any job over $200. When a contractor gives you their license number, don’t just write it down. Go to www1.nyc.gov/site/dca and search their database. You’re checking three things: the license is active, it matches the business name exactly, and there are no serious violations on file.
Also verify their business is registered with the New York Department of State. Search the entity name at dos.ny.gov. If they operate as “Joe’s Roofing” but the registered entity is “Metropolitan Construction Services LLC,” that’s not automatically disqualifying-but you need to know who you’re actually contracting with, because that’s who you’ll sue if things go wrong.
Don’t accept license information verbally or trust it’s “in the paperwork somewhere.” Before the first meeting ends, you should have photographed or written down: their HIC license number, their business registration number, and the exact legal entity name. Takes two minutes. Saves years of litigation.

2. Demand Current Insurance Certificates (And Call to Verify Them)

Here’s what I saw constantly in Brooklyn claims: homeowners had “proof of insurance”-a certificate their contractor emailed them showing general liability and workers’ comp coverage. Looked perfect. Only problem? The policy had been canceled two months before the job started, or the certificate was photoshopped, or the coverage amounts were real but excluded roofing work. I’ve personally documented eleven cases in Brooklyn and Queens where contractors provided fake or expired certificates, then a worker fell or property damage occurred, and the homeowner discovered they were personally liable for $100,000+ in medical bills or repairs.
You need two insurance certificates: general liability insurance (minimum $1 million per occurrence, $2 million aggregate) and workers’ compensation insurance if they have any employees. These must be original certificates issued by the insurance company-not photocopies, not screenshots, not “I’ll send it later.” The certificate holder section should list your name and property address.
But here’s the step nobody does: call the insurance company directly to verify the policy is active and covers the dates of your project. The phone number is printed on the certificate-use that, not a number the contractor gives you. Ask: “Is this policy active? Does it cover residential roofing? What are the current coverage limits?” I caught a Bed-Stuy contractor last year whose certificate showed a real policy number, but when I called, the agent said coverage had lapsed three weeks earlier. The contractor was bidding jobs with an expired cert, betting nobody would verify.
If a contractor resists providing certificates, or says “we’re covered, don’t worry,” you walk. Non-negotiable. In Brooklyn, where most homes are close together and a roofing accident can damage multiple properties, uninsured contractors are lawsuit landmines.

3. Examine Their Permit History and Building Code Knowledge

I evaluated a Crown Heights row house where the contractor replaced the entire roof-new decking, new shingles, new flashing, beautiful work-without pulling a permit. The homeowner didn’t know permits were required. When they went to sell the house two years later, the buyer’s inspector flagged the unpermitted work, and the mortgage company refused to close until the roof was inspected and brought to code. Cost the seller $8,400 in reinspections, engineering reports, and punch-list corrections, plus they nearly lost the buyer.
In New York City, most roof work requires a permit from the Department of Buildings. That includes roof replacement, structural repairs, adding new penetrations (skylights, vents, chimneys), and sometimes even extensive patching. The permit process verifies the work meets code and creates a paper trail that protects you during sale or insurance claims.
When you’re checking out a roofing contractor, ask to see examples of permits they’ve pulled in Brooklyn in the last 12 months. They should be able to show you permit numbers and job addresses (with homeowner details redacted). If they say “we handle all that” but can’t produce permit documentation, they’re either lying or they don’t pull permits-both disqualifying.
Also ask specific code questions: What’s the minimum slope for asphalt shingle installation in NYC? How do you flash a chimney to meet current code? What underlayment do you use for low-slope applications? A legitimate contractor will answer immediately and reference NYC Building Code sections. A fly-by-night operator will give vague answers or say “we follow manufacturer specs” without mentioning code.

4. Get Everything in Writing (Especially the Scope and Warranty)

Williamsburg, 2019. Homeowner hired a contractor based on a handshake and a napkin sketch showing “$8,500, new roof, all materials included.” Job’s finished, looks great. Four months later, ice dams cause leaks around the skylights. Homeowner calls the contractor: “You didn’t install ice and water shield in the valleys.” Contractor: “That wasn’t in our agreement-you wanted basic installation.” No written scope, no way to prove what was promised, no legal recourse. I documented that claim for the insurance company, who denied it because the leak was caused by improper installation, not storm damage.
Before you sign anything or pay a deposit, demand a detailed written contract that includes:

• Exact scope of work: not “replace roof” but “remove existing asphalt shingles down to decking, inspect and replace damaged decking as needed, install synthetic underlayment, install GAF Timberline HDZ shingles in Weathered Wood, install ice and water shield in all valleys and eaves, install new pipe boot flashings, ridge vent, and drip edge”
• Specific materials: brand names, product lines, colors, warranties
• Timeline: start date, estimated completion, weather delay provisions
• Payment schedule: deposit amount, progress payments tied to milestones, final payment upon completion and inspection
• Permit responsibility: who pulls permits, who pays fees
• Cleanup and disposal: who hauls debris, who provides dumpster
• Warranty terms: what’s covered, for how long, who honors the warranty

That last point-warranty-is where contractors bury the problems. I’ve seen “lifetime warranties” that cover materials but not labor (so you pay $3,000 in labor to replace a $40 defective shingle). I’ve seen warranties that require annual inspections at the homeowner’s expense or they void. I’ve seen warranties from manufacturers that the contractor isn’t actually certified to offer.
Ask for two warranties in writing: the manufacturer’s material warranty (usually 25-50 years for shingles) and the contractor’s workmanship warranty (should be minimum 5 years in Brooklyn, where weather is hard on installations). The workmanship warranty should specify exactly what’s covered-leaks due to improper installation, flashing failures, fastener issues-and should be backed by the business entity, not just the individual contractor’s name.
Never accept verbal promises. “We always do it that way” means nothing when the check’s cashed and the crew’s gone. If it’s not in the written contract with a signature, it doesn’t exist.

5. Check Their Actual Work (Not Just Online Reviews)

Online reviews are useful, but they’re also the easiest thing to fake or manipulate. I’ve investigated contractors with 4.8-star Google ratings who left roofs that failed within 18 months. Reviews tell you about customer service and communication-important, sure-but they don’t tell you if the flashing was installed correctly or if the underlayment will hold up in a winter freeze-thaw cycle.
When you’re serious about a contractor, ask for references from jobs completed 2-5 years ago in Brooklyn. Not last month-that roof hasn’t been tested yet. You want to see how their work performs after multiple seasons of Brooklyn weather: ice, wind, summer heat that hits 95° and cooks asphalt shingles, nor’easters that drive rain sideways into every seam.
Call those references and ask specific questions: Any leaks? Any callbacks for repairs? Did the contractor honor the warranty? How did the roof hold up in the last big storm? Then ask if you can drive by and look at the roof from the street. You’re checking for visible problems: shingles lifting or curling, staining that suggests leaks, flashing that’s already showing rust or separation.
If possible, ask to see a job in progress. A legitimate contractor will let you visit an active job site (with the homeowner’s permission) so you can see how they stage materials, protect the property, manage debris, and install components. Watch how the crew handles flashing details around chimneys and vents-those are the spots that leak first if done poorly. At Dennis Roofing, we encourage potential clients to visit our Brooklyn job sites because we know our installations look as good mid-project as they do on completion day.
Also check if the contractor is certified by the shingle manufacturers they use. GAF, CertainTeed, and Owens Corning all have certification programs that require contractors to meet installation standards, carry proper insurance, and maintain good business practices. A GAF Master Elite contractor or CertainTeed SELECT ShingleMaster has been vetted by the manufacturer and can offer enhanced warranties that aren’t available otherwise. Ask to see their certification credentials-these aren’t handed out freely.

What Happens If You Skip These Steps

I’m not trying to scare you, but you need to understand the actual consequences. When you hire an unlicensed contractor or skip the insurance verification, you don’t just risk poor workmanship-you risk legal and financial liability that can dwarf the cost of the roof itself.
If an uninsured worker falls off your roof and is injured, your homeowner’s insurance may refuse the claim, and you can be sued personally for medical bills, lost wages, and damages. In New York, those settlements regularly hit six figures. If unpermitted work causes structural failure or fire, your insurance company can deny the claim and you’re responsible for all repairs-plus you may face fines from the Department of Buildings. If your contractor ghosts you mid-project and you have no written contract, you have almost no legal recourse to recover your deposit or force completion.
I’ve watched Brooklyn homeowners lose their houses over these mistakes. Not exaggerating-actual foreclosures because they couldn’t afford to fix a botched roof job and couldn’t sell the property with obvious defects. The $800 you save by hiring the cheapest bid can cost you $80,000 in legal fees, repairs, and property value loss.

Final Verification Before You Sign

Once you’ve checked licenses, verified insurance, reviewed permits, and examined their work, do one last thing before you sign the contract and hand over a deposit: search for lawsuits and complaints. Check the Better Business Bureau, the NYC Department of Consumer Affairs complaint database, and run a quick New York civil court case search using the business name. You’re looking for patterns-one lawsuit might be a difficult customer, but five lawsuits in three years suggests the contractor doesn’t honor agreements or leaves jobs incomplete.
Also verify their physical business address. Not a P.O. box, not a UPS Store mailbox-an actual business location or verifiable office. Contractors who operate out of a truck with no traceable business location are nearly impossible to pursue legally when things go wrong.
This entire verification process-license check, insurance calls, permit review, reference visits-takes maybe four hours total. Spread over a week while you’re getting bids, it’s barely noticeable. But those four hours are the difference between hiring a professional roofing contractor and hiring a liability.
At Dennis Roofing, we hand every potential client our complete documentation package on the first visit: current HIC license, insurance certificates with our agent’s direct number, permit examples from recent Brooklyn jobs, and a reference list going back five years. We do this because we know experienced homeowners check, and we’d rather work with clients who verify everything than clients who trust blindly and panic later when reality doesn’t match promises.
When you’re ready to check out a roofing contractor properly, start with documentation, verify everything independently, and never accept “trust me” as proof of anything. The contractors who resist this process are exactly the ones you’re trying to avoid.