Educational privatization created new arrangements for funding, provision, and regulation of educational systems and their various stakeholders worldwide. This qualitative study examines the driving forces of privatization in the public education of Ukraine, focusing specifically on the professional roles of school principals who have been compelled by state underfunding to search for external private funds to maintain and develop their educational establishments. Through an exploration of insufficient resources, approaches used to attract external private funding, issues faced, and school principals' attitudes, the study reveals the factors driving privatization, offers examples of how these factors have reshaped principals' professional roles, and discusses how they have adapted to varying degrees to accept the new professional role of fundraisers. Principals viewed this role either as a temporary responsibility caused by lack of state funding during the prolonged economic crisis or as an emergent entrepreneurial responsibility in a society transitioning to a market economy.