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Big Bear Roofing: Rooted in Integrity, Built on Experience


We’re more than just a roofing company—we’re a family-run business dedicated to protecting your home, your investment, and your peace of mind. Rooted in Hartland, the heart of Lake Country, WI, we pride ourselves on delivering exceptional craftsmanship and a personal touch that reflects our deep commitment to our community.


Born and Raised in Wisconsin, Honed Across the Country



Big Bear Roofing is the culmination of a life spent mastering the roofing industry and serving others. Born and raised in Waukesha among a family of entrepreneurs, the values of hard work, perseverance, and integrity were instilled in us from a young age.

Over the years, we've overseen thousands of shingle and flat roof projects, completed countless repairs, and tackled unique challenges like retrofits, standing seam roofing, barn metal installations, and mountain homes with full ice and water shield requirements. From navigating intricate home designs to meeting the demands of storm restoration, we've gained a wealth of knowledge and expertise that we bring to every project.



A Unique Perspective: Roofing and Insurance Expertise



In addition to our extensive hands-on roofing experience, we are licensed insurance adjusters in 30 states, giving us unparalleled insight into the insurance process for both the insured and the insurance companies. We have worked extensively with homeowners and adjusters to ensure that storm restoration claims are handled fairly and transparently. Our experience inspecting homes across Wisconsin, Illinois, Colorado, Florida, and beyond has given us a broad understanding of home construction and the best practices for lasting quality.

Family, Faith, and Community


Big Bear Roofing is built on a foundation of family values—shaped by nearly 20 years of marriage and the blessing of raising six incredible children, from an infant to a seventh grader. We’re proud to call Lake Country our home, where we are actively involved in our church and community, striving to uphold the high moral character and values that God calls us to live by.


We believe our faith is more than a Sunday practice; it’s the compass that guides every aspect of our business. Integrity, honesty, and service are at the heart of everything we do, from the first consultation to the final nail.

At the heart of Big Bear Roofing is Scott Shirley, a dedicated family man with deep roots in Waukesha County. With over 15 years of experience in home inspections, roofing, attics, ventilation, and general contracting, Scott brings a wealth of expertise and certifications across multiple systems. His hands-on knowledge and attention to detail ensure every project is completed with the highest standards of quality and care.


Scott’s love for cars, hunting, and the outdoors reflects his appreciation for craftsmanship and precision. A lifelong resident of Waukesha County, he has built lasting relationships within the community, valuing trust and mutual respect.


Faith and integrity are central to Scott’s work and life. He believes in living out his values daily, not just on Sundays, weaving honesty, service, and a commitment to excellence into every aspect of the business. At Big Bear Roofing, these principles guide the team in providing exceptional care from the first consultation to the final nail.

Our Mission


At Big Bear Roofing, our mission is to provide exceptional roofing solutions while upholding the values that matter most to us: integrity, quality, and service. We understand that your roof is more than just a structure—it’s what protects your family, your memories, and your future. That’s why we treat every project as if it were our own home.



Why Choose Big Bear Roofing?


  1. Expertise You Can Trust: Over 15 years of experience in the roofing industry, specializing in shingle and flat roofs, storm restoration, and unique installations.
  2. Insurance Savvy: Licensed in 30 states, we understand the claims process and advocate for our clients to ensure fair treatment.
  3. Community Values: As locals, we care deeply about our Lake Country neighbors and are committed to upholding the highest standards of service and character.
  4. Family-Focused Service: We treat every client like family because we know what it means to build a home with love and care.


A Personal Promise



Whether it’s a simple repair, a full roof replacement, or storm damage restoration, we approach every project with a commitment to excellence. Our faith, family, and community drive us to provide not only exceptional roofing solutions but also a business you can trust.


Thank you for considering Big Bear Roofing. We look forward to protecting your home with the quality, expertise, and integrity you deserve.


FAQ's

  • My roof leaks. Do I need to have it replaced completely?

    Not always. A leaking roof might just need targeted repairs, but if the damage is extensive or the roof is old, replacement could be more cost-effective. A professional inspection can determine the best solution.


  • How long can I expect my roof system to last?

    The lifespan of a roof depends on the materials and maintenance. Asphalt shingles typically last 20-30 years, while metal or tile roofs can last 50+ years. Regular inspections and upkeep can extend its life.

  • Are your services covered by my home insurance?

    It depends on your policy and the cause of the damage. Most home insurance plans cover roof repairs or replacements caused by storms or accidents but not general wear and tear. Check with your insurer for details.

  • When is the best time to do roofing replacement

    The best time for roof replacement in Wisconsin is typically late spring through early fall (May to October). During these months, the weather is more predictable, temperatures are moderate, and conditions are ideal for proper shingle adhesion and efficient installation. However, with the right precautions, roofing can still be done in winter if necessary.

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