Dick’s Roof Repair, a trusted name in roofing throughout Southeast Wisconsin since 1957, is proud to announce the recipients of its 2025 Free Roof Award: U.S. Army veterans Bob and Alisha Sheriff.
The annual Free Roof Award began in 2020 as a way to give back to the community and honor those who make a difference. Since then, Dick’s Roof Repair has provided a new roof each year to deserving individuals, including a healthcare worker, a firefighter, two educators, a dedicated volunteer, and a veteran.
This year’s award highlights the story of Bob and Alisha Sheriff, both active-duty Army service members who have dedicated their lives to protecting the nation. Bob has served for 19 years, and Alisha for 14 years, with multiple deployments to Iraq and Afghanistan. Recently, the couple purchased their first home as they began raising their three young children and transitioning into civilian life.
Soon after moving in, the Sheriffs discovered their roof was leaking during a heavy rainstorm. Repair quotes were far beyond their means, and as the damage worsened, neighbors nominated the couple for the Free Roof Award. Nominations described Bob and Alisha as selfless and kind, noting their ongoing work with local nonprofits to deliver food, toys, and essentials to families in need.
“At Dick’s Roof Repair, we believe in honoring the people who make our community strong,” said Jeff Milkie, President of Dick’s Roof Repair. “Bob and Alisha embody service, generosity, and resilience. After dedicating so much of their lives to serving our country and helping others here at home, it is our privilege to ensure their family has a safe and reliable roof over their heads.”
For the Sheriffs, the new roof is more than just a home improvement. It is a symbol of gratitude from the community they’ve given so much to.
Dick’s Roof Repair remains committed to carrying on this tradition in the years ahead, continuing to support local heroes and good neighbors who make Southeast Wisconsin a stronger, more connected community.
