Dylan Bailey brings more than 20 years of experience as an independent commercial property and casualty insurance broker, specializing in middle market businesses with a focus on hospitality-related risks. His career advising hotels, restaurants, resorts, and service-driven enterprises has shaped his hospitality-first approach to business ownership.
Born in Knoxville and raised primarily on Hilton Head Island, with time spent in Mobile, Alabama, and boarding school, Dylan developed adaptability and a broad business perspective early on. A 2001 graduate of the University of Mississippi, he has built his career advising business owners on risk strategy, operational resilience, and long-term growth.
In January 2024, Dylan opened IMAGE Studios Knoxville with a long-term vision of developing multiple locations. He was drawn to the brand’s elevated design, entrepreneurial spirit, and commitment to empowering independent beauty professionals. His ownership style centers on being present, listening, and cultivating a culture that blends professionalism with hospitality. He believes that strong systems, financial stewardship, and a supportive environment create the foundation for beauty professionals to thrive.
Dylan lives in Knoxville with his wife, Hallie, and their two sons. Outside of work, he enjoys traveling, golf, and spending time with his family.
