Valor Exterior Partners Enters Wisconsin by Acquiring Dick’s Roof Repair

What happened

Valor Exterior Partners, a Cincinnati-based residential exterior services company and a portfolio company of Osceola Capital, announced on August 20, 2026 that it had acquired Dick’s Roof Repair, a roofing contractor based in Kenosha, Wisconsin. The deal takes Valor into Wisconsin and northern Illinois, and it is Valor’s 10th acquisition since the platform launched in September 2024. Financial terms were not disclosed.

The seller

Dick Milkie founded Dick’s Roof Repair in Kenosha in 1957. He learned the trade from his father, who worked for a roofing company in Racine. His son, Jeff Milkie, is president and runs the company. The third generation is in the business too: Jeff’s children Laura and Steve had joined by 2021, and Josh joined in 2025 as a sales rep and marketing coordinator after a career in media.

The work is residential and exterior. Roofing is the core, from storm-damage repairs and real estate roof inspections to full tear-offs and re-roofs, alongside siding, windows and doors, gutters, and chimney work. The company serves Kenosha, Racine, Walworth, Milwaukee and Waukesha counties in Wisconsin, and Lake and McHenry counties in Illinois. It was voted Best Roofing Contractor in Best of Kenosha 2025, its eighth consecutive win.

“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,” Jeff Milkie said in the announcement.

The buyer

Valor installs, repairs, replaces and maintains roofing, siding, windows, doors, skylights, insulation and decking for homeowners. Its companies run under their own names across New England, New York, Pennsylvania, Delaware, Ohio, Kentucky and Indiana. The most recent before this deal was Associate Roofing, a Braintree, Massachusetts contractor founded in 1975, announced in April 2026 as Valor’s ninth acquisition. The nearest to Kenosha is Louisville-based Unisource Roofing, which serves Kentucky and southern Indiana and joined in November 2025 alongside A. Caspersen Co. of Northeast Ohio, as Valor’s sixth and seventh deals.

Osceola Capital is a Tampa-based private equity firm that invests in lower-middle-market services companies. Valor CEO Jerry Arteaga said in the announcement that the company “will continue to execute on our inorganic growth strategy, seeking out partnerships that expand both Valor’s geographic coverage and service offering across the region.”

What this means for roofing owners

Until this deal, Valor’s westernmost companies were in Ohio, Kentucky and Indiana. Dick’s is its first in Wisconsin or Illinois, so a 69-year-old Kenosha roofer is now the platform’s only operation in a market that runs from Milwaukee County to McHenry County. It also arrived in a quick sequence: five of Valor’s 10 acquisitions have been announced since November 2025.

Jeff Milkie’s stated case for Valor was its record on legacy preservation. An owner weighing a similar buyer can test that kind of claim by checking whether the companies that joined earlier still operate under their own names, as Valor’s nine prior acquisitions do. For a roofer in southeastern Wisconsin or northern Illinois, the practical change is that a three-generation local competitor now sits inside a platform with a private equity sponsor behind it. Owners comparing that route with staying independent can read our guide on selling a roofing business to private equity.

OffDeal is an advisory firm that helps lower-middle-market business owners sell with confidence. Reach out to learn more about our expertise with roofing businesses in Wisconsin.

Own a roofing business with $5M–$100M in revenue? We’re glad to give you an honest read on what it’s worth and who would buy it — no pitch, no pressure. Get a free valuation.

Source: PR Newswire - https://www.prnewswire.com/news-releases/osceola-capital-backed-valor-exterior-partners-announces-acquisition-of-wisconsin-based-dicks-roof-repair-302856432.html