University‐based fundraisers have career paths that are unique in that most do not come to their careers through traditional training programs that are available to other professions, which may impact their expectations of and experiences in their work. Using the conceptual framework of person‐in‐environment fit, this study uses qualitative data from semistructured interviews of 44 higher education fundraisers to understand factors influencing their career trajectories. While formal educational backgrounds do not necessarily provide specific skills necessary for a fundraising career, findings show that many rely on on‐the‐job training, which was at times inadequate. Findings also counter common reports of fundraisers as “falling into the profession” when choosing to join the fundraising field and demonstrate how organizational factors can influence recruitment and retention.