If you hire this pro, you’re covered by a money-back guarantee. Learn more
If you hire this pro, you’re covered by a money-back guarantee. Learn more
About
At Boss Roofing ‑ Siding Experts, protecting homes and properties is what we do best — and we’ve been perfecting it for over 20 years. We specialize in roofing and siding, delivering top-quality materials and expert installation on every project, backed by decades of experience and a commitment to craftsmanship. We’re proud to be the only GAF Master Elite Contractor in the area, which means we offer exclusive warranties and proven, manufacturer-trained installation.
Our team stands out for:
⭐ Decades of experience with residential & commercial roofs
🏆 Presidents Club Award winner (only 3 nationwide)
💯 50-year leak-free warranty options
🛠️ Local crews who care about craftsmanship and cleanup
❤️ A commitment to community — donating roofs to veterans & families in need
When you hire us, you’re not just getting a roof or siding — you’re getting peace of mind, proven reliability, and a company that stands behind every single project.
Overview
Current Top Pro
Hired 24 times
Serves Sterling, IL
Background checked
License verified
48 employees
21 years in business
Business hours
This pro hasn't listed their business hours.
Payment methods
This pro accepts payments via Cash, Check, and Credit card.
Customers rated this pro highly for work quality, professionalism, and responsiveness.
Great 4.8
107 reviews
5
91%
4
4%
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1%
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This pro's rating is a combination of reviews posted by customers both on and off of Thumbtack. Thumbtack cannot verify external reviews.
Your trust means everything to us. Learn about our review guidelines.
Read reviews that mention:
Joseph V.
4 days ago
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Hired on Thumbtack
Austin did a great job on repairing the garage roof. I will be calling in a few years when the garage and house need re-roofing. Thanks, Austin. PS I would have give high marks in all categories, but the app only let me select 3.
Details: Shingles or tiles need to be repaired or replaced • Single-level building • 11 - 20 years old • Asphalt shingles • No, the project is not covered by an insurance claim • Residential • Owner
Roof Repair or Maintenance
behlers5
Nov 15, 2025
•
From Google
Cash Hubbard and his crew did a great job on our roofreplacement! They arrived shortly before 8:00 am and worked steadily throughout out the day to finish the project and depart around 4:00pm. Cash was friendly, professional and answered any questions I had without hesitation. He supervised the crew and ensured that everything was properly installed and that everything was cleaned up at the end of the day. I would highly recommend Boss Roofing!
Boss Roofing - Siding Experts's reply
Thank you so much for sharing your experience! We’re thrilled to hear how pleased you are with your asphalt shingle roof replacement in Sublette. Cash Hubbard and his crew will be grateful for your kind words — they take a lot of pride in providing friendly, professional service and making sure each project is completed with care from start to finish.
It’s great to hear that the installation went smoothly, your questions were answered, and the cleanup met your expectations. We truly appreciate your recommendation and your trust in Boss Roofing.
If you ever need anything in the future, we’re always here to help!
Joel S.
Nov 4, 2025
•
From Google
Great service start to finish. On the first visit, Joey spent a lot of time discussing how they inspect the entire roof and listened to our concerns. After the inspection, he went over what needed to be repaired and how they would repair that area. When the team came out to do the repairs today, again they took the time to listen to our concerns and explained what and how they were doing the repair. They also walked the entire roof and inspected it to ensure there were no other issues. Highly recommend Boss roofing.
Boss Roofing - Siding Experts's reply
Thank you, Joel! We’re so glad you’re pleased with your roof repair in Aurora, IL. Our team takes pride in communication, attention to detail, and lasting results. We appreciate your trust in Boss Roofing & Siding Experts!
April S.
Nov 4, 2025
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From Google
Great communication, prompt service and timely work. Roofing inspection and work was well documented with photos. Both Casey Hofmaster and Teresa Eykamp were great to work with. Casey did a thorough inspection inside and outside to determine what should be done. Theresa was great with communicating before, during, and after work was done and made sure everything was done to our satisfaction before leaving the job site.
Boss Roofing - Siding Experts's reply
Thank you, April! We’re so glad you had a positive experience with your rubber roof project in Sterling, IL. Casey and Teresa take great pride in providing detailed inspections, clear communication, and quality workmanship from start to finish. We truly appreciate your trust in Boss Roofing & Siding Experts!
Sara
Nov 4, 2025
•
From Google
Joe and DeSean came out from Boss for roof repair. Shingles were missing and the ridge vent had to be replaced. The guys were really great, professional and fast. The sales team was honest and communicated everything clearly. Would highly recommend.
Boss Roofing - Siding Experts's reply
Thank you so much, Sara! We’re glad our team — Joe and DeSean — could respond quickly and handle your storm damage roof repair with professionalism and care. Our goal at Boss Roofing & Siding Experts is to provide honest communication and quality workmanship every time. We truly appreciate your recommendation!
FAQs
What should the customer know about your pricing (e.g., discounts, fees)?
Our pricing reflects premium materials, certified installation, and warranties that protect your home for decades, ensuring the best long-term value. To make your project affordable, we offer financing options, flexible payment plans, and our exclusive ‘Roof Now, Pay Later’ program, along with accepting most major forms of payment.
What is your typical process for working with a new customer?
We like to keep things simple for our customers. First, we meet for a free consultation to understand your needs and goals. Then we give you a clear proposal with financing options. Once approved, we handle everything from permits to installation, keeping you informed along the way. At the end, we do a final walkthrough together to make sure you’re 100% happy.
What education and/or training do you have that relates to your work?
With nearly two decades in business, our crews bring thousands of hours of on-the-job training. Each installer is trained in proper roofing, siding, and gutter installation techniques, ensuring quality and durability on every project. We are also proud to be certified GAF Master Elite® Contractors — a distinction earned by only 2% of roofing companies nationwide — which guarantees you the highest standards of installation, product quality, and warranty protection.
