The deal
Valor Exterior Partners, a Cincinnati-based provider of residential exterior services backed by Tampa private equity firm Osceola Capital, has acquired Dick's Roof Repair. Terms were not disclosed.
Dick Milkie founded the company in 1957. It provides roofing, siding and other exterior work for homeowners in southern Wisconsin and northern Illinois. Jeff Milkie, the founder's son and the company's president, continues to lead it.
The deal is Valor's 10th since the platform launched in September 2024, and its first in Wisconsin, extending its footprint across the Great Lakes. Valor also offers windows, doors, skylights, insulation and decking.
Ten acquisitions in under two years is what a PE-backed platform in growth mode looks like. Platforms at this stage are hungry for strong regional names to plant flags in new states, which is exactly what a nearly 70-year-old family business offers. For second-generation owners, the deal also shows a common path: sell the company, keep running it, and let the platform's capital do the heavy lifting.
What this means if you own a roofing or exterior company
- First-in-state deals carry a premium mindset. When a platform enters a new state, it needs a trusted anchor, and that gives the seller leverage.
- Exterior platforms cross-sell. Roofing customers become siding, window and gutter customers, which raises what a buyer can earn from your list.
- Family succession and a sale can fit together. The next generation can stay in charge while the family takes chips off the table.
Source: Valor Exterior Partners announcement, PR Newswire, Aug. 20, 2026. Summary and analysis by V2 Strategy Advisors.