Upside Roof Systems emerged in 2018 from the merger of two roofing companies owned by Mike Kennedy and Austin Railey – boasting over 40 years of combined industry experience. Our smooth transition to a larger company is rooted in an unwavering commitment to customer service. As owners and operators, Mike and Austin handle estimates personally, avoiding the conventional commission-based sales model to build direct trust with customers. We prioritize quality over profit, utilizing top-tier materials and skilled roofers for durable and worry-free roofs. Consistency defines our approach, whether it’s an 800-square-foot home or a 5,000-square-foot estate—each project receives meticulous attention. Every homeowner deserves to feel their project is crucial, and we uphold high standards in every job. What distinguishes Upside? Our commitment, top-tier materials, consistency, and extensive experience. Engage with any Upside team member, and rest assured they are highly qualified for diagnoses and recommendations. From storm damage to insurance claims and energy efficiency, our experience is the bedrock of our business. Mike Kennedy: Owner/ Operator Mike has been in the roofing industry since 1997 working his way up from being the clean-up guy on a crew to owning his own company. He was born and raised in Louisville and attended Waggener high school and the University of Louisville (Exercise Science and Physiology). He enjoys road cycling and mountain biking and formerly spent several years racing competitively. In his down time, he can be found exploring the Parklands, conversing with friends at a local brewery, or relaxing at his Fisherville home with his wife and cats listening to music and enjoying the tranquility. Austin Railey: Owner/ Operator Austin has worked in roofing since 2004 in various capacities. As a native to the city, he was also a Louisville Metro firefighter for many years.  He attended Ballard high school, the University of Kentucky, and the University of Louisville (Exercise Science and Physiology). He enjoys skiing, running, and is active in his church. In his spare time, he works on home improvement projects and spends time with his wife, two daughters and their dog Maggie. Caitlin Barnes: Administrative Coordinator Caitlin has been with Upside since early 2023. She is currently a Business Administration major at the University of Louisville with a marketing minor. She was born and raised in Louisville and attended Fairdale high school. She is an avid reader, often known to finish books in one sitting. Her hobbies include weekends on the water at her family’s lake house, exploring any and every local coffee shop, and hiking trails all over the area with her energetic pup Nala.