The purpose of this study was to examine the effect of professional development experiences on the career competencies of continuing higher education unit leaders (CHEULs). In the American system of higher education, a CHEUL manages an administrative unit that offers educational programs to adult learners (Cranton, 1996). To face the challenges brought forth by disruptive innovation (Christensen, 1997), CHEULs need to improve their career competencies in order to perform successfully in their professional role. Participation in professional development experiences is a common way to develop these career competencies. This qualitative study examined the professional development experiences of 10 CHEULs to analyze their effectiveness in building career competencies. Utilizing the portraiture method (Lawrence-Lightfoot & Davis, 1997), six themes emerged from the study: Diversity of Career Journeys, Factors Influencing Participation in Professional Development Experiences, Reasons for Participation in Professional Development Experiences, Types of Professional Development Experiences, Gaps in Professional Development Experiences, and Strengths in Professional Development Experiences. Discussion and analysis of these six themes form the groundwork for a proposed competency-based professional development model to guide the future professional development experiences of CHEULs.