When you’re responsible for a commercial property, hiring the right roofing contractor isn’t just another task to check off your list—it’s a decision that can affect your building’s long-term performance, safety, and even resale value.
The stakes are high, and unfortunately, not every contractor is as thorough or reliable as they should be. At Old Line Homes, we’ve seen what can happen when a roofing company cuts corners or disappears after the final payment clears. That’s why we always encourage business owners and property managers to slow down and ask the right things before signing any contract.
In this post, we’re walking you through seven smart questions to ask before hiring a commercial roofer. These aren’t just technical checks—they’re tools to help you feel more confident, informed, and in control of your roofing investment.
Why It’s Worth Asking a Few Extra Questions
Not Every Roofer Is Built for Commercial Work
Commercial roofing isn’t a side gig or a scaled-up version of residential work—it’s a specialized field. Materials, installation methods, building codes, and safety regulations all differ, and you need someone who knows the nuances of working on flat or low-slope systems.
If you don’t ask the right questions up front, you might end up with a contractor who’s learning on your roof—or worse, someone who’s not around when something goes wrong.
At Old Line Homes, we believe the best partnerships start with open dialogue. Here’s how to get that started.
1. Are You Properly Licensed and Insured?
The Non-Negotiable
This might feel like a formality, but it’s essential. Your roofer should be licensed to operate in Maryland and carry up-to-date liability insurance and workers’ comp coverage.
Why it matters: If a worker is injured or property is damaged during the job, and your contractor isn’t properly insured, you could be held financially responsible. Don’t just ask—ask to see proof.
At Old Line Homes, we always provide documentation upfront, because trust should be earned before the first nail goes in.
2. What Experience Do You Have With My Type of Roof?
Match the Contractor to the System
Commercial roofing materials vary—EPDM, TPO, PVC, metal, and built-up systems all require different tools and techniques. Make sure your roofer has specific experience with your type of roof and can explain the unique challenges it presents.
Why it matters: A team that’s unfamiliar with your roofing system may use incorrect materials or methods, leading to premature failure and costly repairs.
Our crews at Old Line Homes are trained and experienced with all major commercial roofing types, and we tailor each project to the unique structure of your building.
3. Can You Walk Me Through the Inspection and Estimate Process?
Transparency Starts on Day One
Before work begins, your contractor should take time to walk your roof, identify potential issues, and provide a detailed estimate—not just a ballpark figure. Ask how they assess your roof and how their estimates are structured.
Why it matters: A vague or overly simple quote might be missing key components. And if they can’t explain their process clearly, it may be a sign they’re not paying attention to the details.
At Old Line Homes, we believe every client deserves a detailed, transparent estimate backed by a thorough inspection—and yes, photos are included.
4. What Kind of Warranties Do You Offer?
Know What You’re Getting—And for How Long
You should be offered two types of warranty coverage: one for materials (typically from the manufacturer) and one for workmanship (from the contractor). Don’t be afraid to ask for both in writing and have them clearly explained.
Why it matters: A strong warranty isn’t just a piece of paper—it’s protection against future expenses if something goes wrong with your roof.
Because Old Line Homes is a certified installer for top brands like GAF, our customers often qualify for extended warranties. And we stand behind our craftsmanship with a strong workmanship guarantee.
5. What Safety Measures Do You Take on the Job?
Safety Is Professionalism in Action
Commercial roofing work—especially on large or multi-level buildings—comes with serious risks. Any contractor you hire should have written safety protocols, training procedures, and equipment in place.
Why it matters: A company that prioritizes safety is more likely to care about doing the rest of the job right, too. And if something goes wrong and safety isn’t followed, you could face liability.
Old Line Homes follows OSHA guidelines, trains all crews in jobsite safety, and ensures every project is conducted with your property—and people—in mind.
6. How Do You Handle Changes or Surprises During the Project?
Because Roofing Never Goes Exactly as Planned
Let’s face it—even the best-laid roofing plans can run into surprises: hidden damage, unexpected weather, outdated structures. What matters most is how your contractor handles those curveballs.
Why it matters: You want a roofer who communicates early and often, explains your options, and keeps your project on track—not someone who springs surprise invoices on you mid-job.
With Old Line Homes, our project managers keep you informed every step of the way. If something changes, you’ll know exactly what’s happening—and why—before we move forward.
7. What Support Do You Offer After the Project Is Finished?
Roofing Is a Long-Term Relationship
A quality roofing job doesn’t end when the trucks pull away. Ask whether your contractor offers annual inspections, maintenance plans, or emergency service options.
Why it matters: Even a well-built roof needs periodic attention. And when repairs or inspections are needed down the line, it’s a lot easier to work with someone who already knows your building.
We offer commercial roof inspections, scheduled maintenance, and priority response for our clients. Because at Old Line Homes, we’re not just here for the project—we’re here for the life of your roof.
Choose a Roofing Partner You Can Count On
When you know what to ask before hiring a commercial roofer, you take control of the process—and protect your property from missteps. The goal isn’t just to find someone who can “do the job.” It’s to find someone who will do it right, stand behind their work, and make your life easier along the way.
If you’re planning a commercial roofing project, Old Line Homes is here to be that partner.
Give us a call or email [email protected] to schedule a free consultation. We’ll walk your roof, answer your questions, and provide a clear plan tailored to your building.
Because roofing isn’t just about shingles and sealants—it’s about trust, accountability, and knowing you’ve made the right call for your business.