As non-profit organizations (NPOs) increasingly adopt business-like practices—a phenomenon known as organizational rationalization—they often appoint leaders with for-profit experience to enhance efficiency and financial performance. While such cross-sector leadership brings valuable managerial skills, its impact on NPO performance is not well understood. This study examines the nonlinear relationship between a non-profit CEO's for-profit experience and a key financial performance indicator: net revenue. Drawing on transfer learning theory and concepts of organizational fit, we hypothesize that CEOs with moderate for-profit experience achieve superior financial outcomes compared to those with minimal, extensive, or no such experience. Additionally, we explore how the CEO's sectoral fit moderate this relationship. This research contributes to the literature on leadership effectiveness and cross-sector mobility by highlighting the importance of sector-specific experience levels and adaptability. Practically, it informs NPOs on strategic considerations for leadership selection and development to optimize financial performance without compromising core values.