Postsecondary education is constantly changing and the role of the chief student affairs officer must evolve to meet the demands of the shifting social, political, and administrative needs of their student population and institution. The intent of this study was to identify the knowledge, skills, and competencies required of chief student affairs officers to be effective and successful in contemporary and future higher education contexts. To provide clarity to the obligations of the executive-level role, the study offers an understanding the complexity of chief student affairs officers' responsibilities in a rapidly shifting postsecondary environment. Participants of the study were current chief student affairs officers who engaged in organized groups based on location, institutional type, athletic conference, or state higher education system. Through a qualitative methodology, with semi-structured, group interviews, the study allowed for data gathering from multiple chief student affairs officers at varied institutional types and locations. Data were collected from 13 focus groups with a total of 68 participants during either during established meetings or via online video conferencing. Findings of the study contribute to the knowledge base of effective practice and preparation for successful and effective chief student affairs officers and provide evidence-based data from which to build continuing education and ongoing professional development. Recommendations are offered for individuals currently in the chief student affairs officer position, those aspiring to the role, graduate programs in doctoral education, search firms, and professional associations that provide ongoing educational offerings for executive leaders in postsecondary education. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]