Start with licensing and insurance, always
Licensing and insurance are the two non-negotiables on any roofing checklist. A contractor license is not the same as a business license, and mixing up the two is one of the most common mistakes homeowners make. In Oregon, the contractor license is the state-issued CCB number (ours is CCB #203933). Ask every contractor for theirs and verify it directly with the CCB.
Insurance is just as specific. You need two separate certificates: general liability, which covers damage to your property, and workers' compensation, which covers the crew if someone gets hurt on your roof. If a contractor cannot produce both on request, the conversation is over.
One more detail most people miss: ask for the certificates of insurance sent directly from the contractor's insurance provider, not a copy the contractor hands you. Handed-over copies can be outdated, or worse.
- "Can you provide your contractor license number so I can verify it?"
- "Do you carry general liability insurance? What is the coverage limit?"
- "Do you carry workers' compensation for everyone on my job?"
- "Do your subcontractors carry their own insurance, or are they covered under yours?" If a subcontractor gets hurt on your property and nobody covers them, that problem can land on you.
Who pulls the permit, and what does it cost?
The contractor pulls the permit, full stop. Permits are not optional, and skipping them can affect your insurance claims and complicate a future home sale. If a contractor suggests skipping the permit to save money or speed things up, that is a red flag worth walking away from.
A contractor who handles permits without being asked is telling you something important: they run a legitimate operation. A contractor who hesitates, or tries to talk you out of it, is telling you something important too. Requirements vary city to city across the Portland metro, and your contractor needs to know the local rules, not just the general ones.
- "Will you pull all required permits for this project?"
- "Are permit fees included in my estimate, or billed separately?"
- "Who schedules and manages the inspection?"
- "How will permit timelines affect my start date?"
Contract clarity: warranties, pricing, and change orders
This part of the checklist deserves the most attention, because the contract governs everything that happens after the handshake. Start with warranties. There are two separate warranties on every roofing job, and you need both in writing. The manufacturer warranty covers defects in the materials themselves, and its terms often depend on whether the installer is certified for that product line. The workmanship warranty covers installation errors, comes from the contractor, and varies widely. Ask for the duration and coverage of each, specifically.
On pricing, ask whether the number is fixed or allowance-based. Decking damage is common and usually hidden until tear-off, so a good contract includes a per-sheet price for decking repairs agreed before work begins, instead of a surprise invoice at the end.
Change orders are where most roofing disputes start. Every change to scope, price, or timeline should be written, priced, and approved by you before the crew touches it. Never approve a verbal change order. If a crew member says they found more damage and need to keep going, ask them to pause until the paperwork is signed. A reputable contractor will not push back on that.
On payment, a reasonable structure is a deposit at signing, a progress payment at a defined milestone like tear-off completion, and a final payment after your walkthrough. Paying in full before the job is done removes your leverage. The contract should also address weather delays, because around here, there will be weather.
Materials, crew, and cleanup: the quality questions
Price comparisons only make sense when you are comparing the same materials and workmanship. Ask every contractor to name the brand, product line, and performance rating of the roofing system they are proposing. There is a real difference between a bargain three-tab shingle and an architectural shingle rated for serious wind, and you deserve to know which one is in your bid. If you want the background first, our roofing 101 guide covers the basics in plain language.
Ask about ventilation too. It sounds like technical trivia, but proper attic ventilation directly affects whether your shingle warranty stays valid and how long the roof lasts. A contractor who cannot explain their ventilation approach may void your manufacturer warranty without ever realizing it.
On cleanup, a thorough contractor runs a magnetic nail sweep across the yard and driveway, hauls off all debris the same day, checks the gutters for roofing debris, and does a final walkthrough with you before final payment. Ask for references from jobs completed in the last year, close to home. References in Damascus, Clackamas, or Happy Valley are a lot easier to verify than a list of names from three states away.
- "Are the workers on my job your direct employees or subcontractors?"
- "Who supervises the crew on site, and will that person be there daily?"
- "What quality control process do you use during installation?"
- "How do you handle attic ventilation as part of this project?"
After the job: build yourself a roof folder
Once the job is done, your paperwork is your protection. Keeping every roofing document in one place, physical or digital, is the best support you can have for future warranty claims, insurance claims, and home resale. It is not complicated, but most homeowners skip it and regret it later.
Lien waivers deserve a specific mention. If your contractor uses subcontractors or buys materials on credit, those parties can put a lien on your property if the contractor does not pay them, even if you paid the contractor in full. A lien waiver from each party confirms they were paid and releases any claim against your home.
And register your manufacturer warranty directly with the manufacturer, not just through the contractor. Some warranties require homeowner registration within a set window after installation to be valid. A professional roof inspection every few years, documented in the same folder, rounds out the record nicely.
- Signed contract and final estimate
- Permits with inspection sign-off sheets
- Manufacturer warranty registration confirmation
- Contractor workmanship warranty document
- Before, during, and after photos of the roof
- Lien waivers from subcontractors and suppliers
What I've learned from a decade of roofing in the Portland metro
I started French Roofing in 2014, and I have seen homeowners get burned in most of the ways there are. The classic is the storm chaser who shows up after bad weather, offers a fast quote, collects a big deposit, and either disappears or delivers work that fails within a couple of years. Those outfits use pressure tactics and vague paperwork precisely because they know most people will not push back.
The homeowners who come out fine are the ones who ask questions. Not hostile ones, just direct ones. "Can I see your license number?" "Can you send me your insurance certificates?" "Can we put that change in writing?" Those three questions alone have saved people real money. A legitimate contractor answers all three without blinking.
Permits are where a lot of contractors cut corners quietly, assuming homeowners do not know or care. Skipping one might save a few days, but it creates real problems when you sell the house or file a claim. We pull permits on every job. It is not extra credit. It is just how the job is supposed to be done. And if a contractor gets defensive when you ask about insurance or change orders, believe what they are showing you.