Claypool has realized success in the field of architecture and city planning while working in the administrations of two Philadelphia mayors and serving as the executive director of the Philadelphia chapter of the American Institute of Architects. As the executive director of the Philadelphia chapter of the American Institute of Architects, Claypool created the independent Center for Architecture, which is responsible for the DesignPhiladelphia Festival, an annual festival highlighting the work of local designers, architects and creative professionals. He also led efforts to raise millions of dollars for the Charter High School for Architecture + Design, at which students can start a career path toward architecture. Claypool was nominated by classmate Kenneth Orenstein (ADL ‘71).