Online executive education courses are a specialized mode of learning used by organizational leaders to develop knowledge in discrete subjects. Universities that offer these courses may lack the technology skills to develop such courses with supportive artificial intelligence (AI) technologies. Instructors of such courses serve as adjuncts who are industry practitioner organizational leaders with experience in using AI in their workplaces. Students of online executive education courses are typically organizational leaders who may expect to encounter AI as a course tool. This qualitative study posed three research questions to address instructor and student perceptions about AI in online executive education: What are instructors' perceptions of AI applications in online executive education courses? What are organizational leader students' perceptions of AI applications in online executive education courses? In what ways, if any, would having AI applications in online executive education courses improve instruction and support organizational leader learning transference (viz., leadership) to workplace environments? Online collaborative learning theory and systems theory served as the theoretical frameworks for understanding how leaders construct knowledge for themselves and their organizations. The researcher used a qualitative case study design and identified a sample of 12 instructors and participants from the researcher's LinkedIn network. Inductive coding of recorded interviews allowed the researcher to identify thematic awareness of online collaborative learning theory and systems theory as a basis for establishing AI as a technology to instructors and students. Future recommendations include deploying AI tools in online executive education courses to quantitatively measure the effect on the experiences of instructors and organizational leaders. [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.]