Against the background of an increasing shortage of school principals in Germany, it appears to be of central importance that school principals perceive themselves as successful in their position (subjective career success) and can also be considered successful on the basis of factors such as salary (objective career success), as these factors can have an impact on the experience of stress and motivation. The aim of the study was to analyze, which determinants from the areas of socio-demographics, (objectified) human capital and (organizational) support measures influence the career success of German school principals. The study uses data from the Leadership in German Schools 2020 (Cramer et al. 2020) study, which was collected by the Forsa Institute for Social Research and Statistical Analysis between September and November 2019. The population for the survey comprised all school leaders at general education schools in Germany. In this group, a randomly selected sample of n = 405 school principals, representative of Germany, was surveyed using a standardized and piloted online questionnaire. The results indicate that there is a link between the perceived career success and university qualifications and qualifications at a state institute. In contrast, no statistically significant correlation was found between income and qualification measures and mentoring. Female principals have a lower income than male principals, even after controlling for a large number of covariates.