Graduating from Seneca high school in 1993, Derwin received an Associate Degree in Computer Science in 1997. After working in IT for 20 years, he returned to school, receiving a Bachelor of Science degree in Interdisciplinary Business Studies in 2017. In 2019, he obtained a Master of Business Administration degree from the University of Louisville and the University of Kentucky. Derwin is currently employed with Humana as the Manager of Technology Solutions.