Joseph T. O'Brien

O’Brien founded Four Leaf Roofing & Windows in 1994 after completing service in the United States Navy, building a veteran-owned exterior contractor that still runs from New Berlin. More than three decades later he remains the named founder behind a Milwaukee-metro shop that installs roofs, windows, siding, and gutters with an in-house crew and no subcontractors.

Four Leaf markets CertainTeed ShingleMaster™ PRO certification, Master Craftsman–trained installers, a lifetime workmanship warranty, and a fifty-point post-installation check. Public materials cite roughly one hundred sixty five-star Google reviews and a 4.9-star rating across New Berlin, Milwaukee, Waukesha, and Brookfield.

The company holds Wisconsin contractor licensing and presents storm-damage documentation, insurance coordination, and year-round exterior work as core services. O’Brien’s Navy-to-roofer arc and long New Berlin headquarters keep Four Leaf positioned as a local veteran-owned exterior brand rather than a storm-chasing out-of-town crew.