Education is one sector being challenged by aging staff, as well as by increased pressure to innovate. In order to cope with these challenges, educational institutions require teaching staff members, who include teachers, support staff and managers, to show a high level of employability. In this survey-based study, the predictive value of quantitative and qualitative job demands, job autonomy and self-directed learning orientation for three employability competences (occupational expertise, personal flexibility, anticipation and optimization) was investigated using a Dutch sample (N = 3139). Moreover, three teaching staff age groups were compared: < 35 years old (young), 35-50 years old (middle-aged), and > 50 years old (senior). Path analysis results showed that self-directed learning orientation was positively associated with the three employability competences across all three different age groups. Positive relationships across age groups were also found between quantitative job demands and occupational expertise, and between qualitative job demands and personal flexibility. In addition, multi-group comparisons revealed age differences in our model relationships. The relationship between self-directed learning orientation, on the one hand, and personal flexibility and anticipation and optimization on the other, was stronger for seniors in comparison with the young employees. For the young employees, the role of autonomy was more important in enhancing their occupational expertise. Implications for school principals and HRD managers are discussed. Promoting a self-directed learning orientation and custom-made workplaces that take into account age differences among teaching staff members appear to be key for protecting and enhancing sustainable employability.