Choosing the right roofing contractor is one of the most important decisions you’ll make as a homeowner or commercial property owner. Whether you're installing a new roof, replacing an old one, or simply making repairs, the skill and integrity of your roofer can directly impact the quality, longevity, and performance of your roofing system.
With so many contractors offering services in the Massachusetts area — and horror stories about shoddy workmanship or disappearing deposits — how can you ensure you’re hiring the right team?
At Associated Roofing, we’ve proudly served Braintree and surrounding communities for decades. We’ve seen what can go wrong when property owners work with underqualified or dishonest contractors — and we want to help you avoid the same fate. That’s why we created this detailed guide to help you navigate the hiring process and ask the right questions from the start.
Roofing is not just another home improvement project. It’s one of the largest, most complex, and cost-intensive repairs or upgrades you can make. A roof protects everything underneath it — your family, belongings, equipment, and the very structure of your property.
Here’s why the contractor you choose makes all the difference:
In short, hiring a trustworthy, qualified roofing contractor isn’t just smart — it’s essential.
Before diving into what to ask, let’s cover what to avoid. Be cautious of any contractor who:
Pressures you to signUnfortunately, fly-by-night roofers often appear after major storms, offering “quick fixes” at suspiciously low prices — and disappearing before problems arise.
Make sure your roofer holds the appropriate licenses for the state and carries both:
Ask for documentation, and verify it with the provider if necessary.
Longevity in business is often a sign of consistency and reliability. Contractors who have been serving the local area for many years are more likely to deliver quality work and stand behind it.
Ask for recent references — preferably within the last 12 months — and check online reviews through platforms like Google, Yelp, or the Better Business Bureau. A reputable contractor will have a proven track record of satisfied customers.
A knowledgeable contractor should be able to explain the pros and cons of different materials (asphalt, architectural shingles, metal, etc.) based on:
Beware of anyone who pushes one option without understanding your needs.
Top roofing manufacturers (like GAF or CertainTeed) certify contractors who meet specific standards. Certified roofers can offer enhanced warranties that non-certified installers cannot. This is especially important for protecting your investment long-term.
The estimate should clearly outline:
Request a written, itemized estimate and avoid contractors who provide only vague ballpark numbers.
Replacing a roof is messy. Ask how the crew will protect:
They should also outline how they’ll handle the cleanup and disposal of old materials.
It’s important to know:
You want a reliable point of contact to handle communication and ensure quality control.
While weather can affect scheduling, your contractor should still give you:
This helps you plan around the project and hold the team accountable.
In addition to manufacturer warranties on materials, a trustworthy roofer will offer a workmanship warranty on labor. This means they’ll come back and fix any installation issues at no cost within a specified time (typically 5–10 years).
Be cautious of any contractor who demands full payment upfront. A typical payment schedule might be:
Make sure all terms are clearly outlined in the contract.
Roofing projects often reveal surprises (like rotted decking or inadequate ventilation). Ask how the contractor will communicate additional findings, provide updated estimates, and get your approval before proceeding.
The contractor should handle permitting and ensure the work meets all Massachusetts building codes and local ordinances. Failing to pull permits can result in fines and problems with future home sales.
After the job is complete, your contractor should:
A thorough cleanup is a sign of a professional, customer-focused contractor
A portfolio of past projects can help you evaluate the quality of their craftsmanship and see how different roofing materials look once installed.
While many contractors may have similar pricing or offer the same products, the experience of working with them can vary greatly.
Here’s what sets the best apart:
At the end of the day, trust your instincts. If a contractor makes you feel rushed, uncomfortable, or confused, they’re probably not the right fit.
Before you hire your roofer, make sure you:
✔ Have a signed, written contract that outlines scope, timeline, materials, warranties, payment schedule, and more.
✔ Understand what happens in case of delays, weather issues, or unexpected findings.
✔ Know who to contact with questions during the project.
✔ Have verified licenses and insurance coverage.
✔ Have received and verified references or reviews.
If you're looking for a licensed, experienced, and highly rated roofing contractor in the Braintree or South Shore area, Associated Roofing is here to help. We've been protecting homes and businesses across Massachusetts for decades with expert installations, honest advice, and quality you can count on.
Call us today at (781) 512-6773 or reach out through our contact form at https://www.associatedroofing.com/contact/. We’re happy to answer your questions, provide a free estimate, and help you feel confident in your roofing investment.