This qualitative study explores the perceptions of NACADA leaders regarding institutional and structural sources, obstacles, and opportunities related to learning and professional development (PD) for primary-role academic advisors. Through semi-structured interviews with 17 NACADA leaders, the study identifies three key themes: the critical role of professional associations in supporting learning and growth, substantial financial and structural barriers to PD, and the essential need for institutional recognition and support. The findings highlight the complexities academic advisors face in enhancing their skills and professional standing, emphasizes the importance of professional communities, and identifies the challenges posed by current institutional frameworks. Implications for fostering a supportive environment for advisor learning and PD are discussed, along with recommendations for future research.