Full Name
Andrea Chesley
Job Title
Dean of Enrollment and Financial Aid
School/Organization
Wayland Academy
Speaker Bio

Andrea is the Dean of Enrollment and Financial Aid at Wayland Academy in Beaver Dam, WI. She holds a Bachelor of Fine Arts in Choreography and Post Baccalaureate in Secondary Education from Arizona State University and is a Masters of Business Administration candidate at the University of Wisconsin- Madison for 2027. Andrea relocated to Beaver Dam, WI from East Hampton, New York, where she served as the Director of Enrollment Management of Ross School for four years. Prior to that, she was the Assistant Director of Admissions at Idyllwild Arts Academy, a private boarding arts high school in Southern California. At Ross School and Idyllwild Arts, Andrea developed successful domestic and international recruitment strategies, taught courses, coached teams, was a dorm parent, and fell in love with boarding school and the communities surrounding them.

Previously, Andrea taught, coached, and served as Chair of Performing Arts at Peoria High School for four years and assisted in the writing of the curriculum that became the Arizona Standards of Education for Dance in Phoenix, AZ before moving to Los Angeles in 2009. In LA, Andrea pursued a career in dance and acting and performed her stand-up comedy at legendary LA venues such as the Hollywood Improv and the Comedy Store. As an amateur chef, she competed on the 5th season of the Great Food Truck Race on the Food Network, and (spoiler alert) came in 2nd place. She is also a founding board member of Kern Dance Alliance, a dance advocacy organization in Kern County, CA.

In her spare time, she loves to write, travel, and eat. 

Andrea Chesley