Osceola Capital-backed Valor Exterior Partners Announces Acquisition of Wisconsin-based Dick's Roof Repair
Osceola Capital-backed Valor Exterior Partners has acquired Dick's Roof Repair, its tenth acquisition since launching in 2024, extending the roofing platform into Wisconsin and northern Illinois.
CINCINNATI, Aug. 20, 2026. Valor Exterior Partners, a portfolio company of Osceola Capital, has acquired Dick's Roof Repair, expanding the platform's footprint into Wisconsin and northern Illinois. The deal is Valor's tenth acquisition since the platform launched in September 2024.
Dick's Roof Repair, founded in 1957 by Dick Milkie and now led by his son Jeff Milkie, provides roofing, siding, and other exterior home services to residential homeowners across southern Wisconsin and northern Illinois.
"We are excited to welcome the Dick's Roof Repair team to the Valor family and further expand the platform's footprint in the Great Lakes region," said Jerry Arteaga, CEO of Valor. "Over the past several decades, DRR has earned a strong reputation in the region as a trusted provider of exterior services to homeowners, making it a natural fit to join Valor."
"The Valor team's dedication to quality and excellence combined with a strong track record of legacy preservation makes them a great fit to help Dick's Roof Repair continue into its next phase of growth," said Jeff Milkie, President of Dick's Roof Repair.
Valor Exterior Partners, headquartered in Cincinnati, specializes in the installation, repair, replacement, and maintenance of roofing, siding, windows, doors, skylights, insulation, and decking. Osceola Capital is a Tampa-based private equity firm that invests in lower middle-market services companies, typically with EBITDA of $2 million to $10 million.