Kiley graduated from the University of New England as a double major, with a bachelors in Elementary Education and a bachelors in Health, Wellness and Occupational Studies. Kiley did her student teaching in a fourth grade classroom and worked for AmeriCorps for two years in a fourth and fifth grade classroom in Maine. Previously, she worked at an elementary school in Rhode Island as a teacher assistant in a kindergarten classroom and a substitute teacher in classrooms kindergarten to fifth grade. Kiley grew up on Block Island, observing and working with an occupational therapist for many years, including co-instructing a move and groove handwriting club for students six to ten years old. Currently, she is getting her masters in Occupational Therapy at Salem State University. During her free time, she likes to go to the beach and go skiing.