A Boutique Roofing Company Built on Family & Craftsmanship

David Wilk’s path into roofing began early. At just 16 years old, he started working summers on roofing crews, learning the trade from the ground up. What began as a summer job quickly became a passion, not just for roofing itself, but for how it should be done.

As David gained experience, he began to notice a pattern in the industry: rushed installations, corners being cut, projects lacking proper oversight, and homeowners left with unanswered questions. He knew there had to be a better way. Rather than accepting the status quo, David committed himself to mastering the craft, pursuing advanced training, manufacturer certifications, and hands-on experience with complex roofing systems few contractors were willing to take on.

At the same time, David recognized that craftsmanship alone wasn’t enough to build a truly exceptional company. While continuing to work in roofing, he attended college for business management, learning how to operate a company with structure, accountability, and long-term vision. His goal was never growth for growth’s sake — it was to build a company that valued quality, transparency, and trust above all else.

After graduating, David founded Wolf Development alongside his brother with a clear mission: not to be the biggest roofing company, but the best specialized roofing company in Chicagoland.

As Wolf Development grew, so did David’s reputation within the industry. Builders, architects, and general contractors began seeking him out for guidance on complex roof designs, material selection, and installation strategies. Today, David is widely regarded as an industry expert, often consulted by other professionals and trusted to share his knowledge through training, collaboration, and hands-on problem solving on challenging projects.

Today, David personally oversees every project Wolf Development takes on. From the initial consultation to material sourcing, coordination, and final walkthroughs, he remains directly involved at every stage. By intentionally keeping the company boutique, David ensures that no project is rushed, no detail is overlooked, and every homeowner receives the level of care and accountability they deserve.

For David, roofing isn’t just a business, it’s a craft, a responsibility, and a reflection of his family name.

Like his brother, Paul Wilk began roofing at the age of 16, learning the trade through hands-on experience in the field. From the very beginning, Paul gravitated toward the technical side of the work — the precision, problem-solving, and discipline required to install complex roofing systems correctly.

Paul’s passion has always been in execution. He understands that even the finest materials mean nothing without proper installation, and that the smallest details like flashing transitions, fastener placement, ventilation, and sequencing are what ultimately determine whether a roof performs for decades or fails prematurely.

As Head of Operations, Paul manages the entire installation process for Wolf Development. He leads the crews on-site, ensures every system is installed to exact manufacturer specifications, and maintains strict quality standards across all projects. His role is hands-on and detail-driven, overseeing everything from daily workflow and safety to final finishing touches.

Paul is also known for his calm, methodical approach on complex projects, especially those involving slate, tile, copper, and custom architectural details. Homeowners regularly comment on the professionalism, cleanliness, and organization of Wolf Development job sites, a direct reflection of Paul’s leadership in the field.

Together with David, Paul helps ensure that every Wolf Development roof isn’t just visually stunning, but structurally sound, weather-tight, and built to stand the test of time.