Skip Wilson began his career in 1999 at Ryder Transportation in Waterville washing and fueling trucks. While at Ryder,  he held positions as a Tire and Alignment Tech, Customer Service Coordinator, and in the Parts Dept. Eventually he worked his way into a supervisor role in the shop. In 2009, Skip began his career with Kris-Way Truck Leasing as a Service Manager at the Waterville branch.