Our Story: Built on Hard Work, Sustained by Family
Windward Roofing & Construction was founded in 1984 by Randy Kuhn, a skilled tradesman with a clear vision: build a commercial roofing company grounded in honest work, fair pricing, and the kind of craftsmanship that speaks for itself. Starting with a small crew and a commitment to doing things right, Randy began taking on commercial roofing projects across Chicago's West Side, earning a reputation one rooftop at a time.
In those early years, Randy handled everything from estimating and material procurement to climbing the ladder himself. He built relationships with building owners, property managers, and general contractors by consistently delivering quality work on time and within budget. Word spread, and what started as a one-crew operation grew steadily throughout the late 1980s and into the 1990s as Windward expanded into larger commercial and industrial projects across the greater Chicago metropolitan area.
What makes Windward different from other roofing contractors is the family foundation at its core. Randy's sons grew up in the business, spending summers on jobsites, learning the trade from the ground up, and absorbing the values their father instilled: show up early, work hard, keep your word, and never cut corners. That hands-on upbringing gave the next generation not just technical expertise, but a deep understanding of what it takes to run a roofing company that clients trust with their most valuable assets.
Today, Windward is in its second generation of family leadership, and that continuity is one of our greatest strengths. The transition from founder to the next generation was not a corporate handoff but a natural evolution, built on decades of shared experience and a unified commitment to the standards Randy established more than 40 years ago. Our clients benefit from the institutional knowledge and long-term perspective that only a multigenerational family business can provide.
Four Decades of Growth and Excellence
Over the past four decades, Windward has grown from a local Chicago roofing company into a regional commercial roofing contractor serving five states. We have completed more than 10,000 projects ranging from small retail roof repairs to multimillion-dollar industrial installations spanning hundreds of thousands of square feet. Our growth has been intentional and disciplined, expanding only when we could maintain the quality and personal service that define our brand.
Our service area now encompasses Illinois, Wisconsin, Michigan, Indiana, and Florida, where we have established a growing presence in new construction and general contracting partnerships. Despite this geographic expansion, our headquarters remain at 919 South Sacramento Boulevard in Chicago, the same neighborhood where Randy Kuhn started the company. That connection to our roots is something we take pride in.
Windward's service capabilities have expanded well beyond roofing to include waterproofing and sheet metal fabrication. This diversification allows us to serve as a single-source contractor for building envelope projects, reducing coordination complexity and ensuring consistent quality across multiple trades. Whether a project calls for a complete roof replacement, below-grade waterproofing, or custom sheet metal work, Windward has the in-house expertise to deliver.
Manufacturer Partnerships and Certifications
Windward Roofing maintains certified installer status with the commercial roofing industry's most respected manufacturers, including Carlisle, Versico, Elevate, Johns Manville, ERC Systems, Sika, GAF, Tremco, and IKO. These certifications are not simply badges on a website. They represent a verified commitment to ongoing training, quality installation practices, and adherence to manufacturer specifications. Our certified status enables us to offer the strongest warranty programs available, giving our clients long-term protection and peace of mind.
We are also proud to be a BBB Accredited Business and a GAF Certified Contractor, reflecting our dedication to ethical business practices, customer satisfaction, and technical proficiency. These accreditations are earned through demonstrated performance, not purchased, and we work every day to uphold the standards they represent.
Our Commitment to Safety
Safety is a non-negotiable priority on every Windward jobsite. Our crews are OSHA-trained, participate in regular safety meetings, and follow comprehensive safety protocols that exceed industry standards. We maintain an active safety program that includes fall protection training, hazard communication, equipment inspection procedures, and drug-free workplace policies. Every superintendent and foreman is empowered to stop work if they observe an unsafe condition, no questions asked. We believe that protecting our people is the foundation of protecting our clients' properties.
Community and Industry Involvement
As a Chicago-based family business, Windward is deeply invested in the communities where we live and work. We support local organizations, participate in industry associations, and mentor the next generation of skilled tradespeople. Randy Kuhn built this company on the belief that a business should give back to the community that supports it, and that principle continues to guide our involvement today. From sponsoring youth sports programs to contributing to neighborhood improvement initiatives, Windward is committed to being more than just a roofing contractor. We aim to be a responsible corporate citizen and a positive force in the communities we serve.
