How Family-Owned Culture Scales to 29 Locations with Darrell Bailey
April 16, 2026
In this episode of Under the Roof, hosts Todd Kavanaugh and Matthew Elban sit down with Darrell Bailey, General Manager of Baker Roofing's Harrisonburg branch for 22 years, to explore what it takes to build a consistently high-performing team, lead with curiosity rather than fear, and create meaningful impact in your local community.
In this episode of Under the Roof, hosts Todd Kavanaugh and Matthew Elban sit down with Darrell Bailey, General Manager of Baker Roofing's Harrisonburg branch for 22 years, to explore what it takes to build a consistently high-performing team, lead with curiosity rather than fear, and create meaningful impact in your local community.
What You’ll Learn:
- How to transform fear into opportunity through curiosity
- The leadership currency framework
- Why consistency beats innovation in local markets
- The power of genuine community connection in business
- How to delegate effectively without losing control
- The importance of finding daily fascination in your work
Darrell Bailey is the General Manager of Baker Roofing Company's Harrisonburg branch, a position he has held for almost 22 years since the branch's inception in 2004. With vast expertise in roofing operations, team leadership, and community engagement, Darrel has built a reputation for consistency, quality, and genuine care for both his team and customers. His leadership approach, grounded in emotional intelligence, continuous learning, and ethical decision-making, has established the Harrisonburg branch as a model of stability and reliability within Baker Roofing's national footprint.
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