Digitalization, skills shortage and the prospect of an aging workforce have put the topic of older workers and lifelong learning high on the agenda of both politics and organisations. In the light of these challenges, organisations are dependent on using the potential of their older employees and fostering the continuation of careers in later life. Nevertheless, older employees often face barriers in their career advancement owing to persistent conscious and unconscious stereotypes, such as being unable to learn new technologies. Against this background, our study analyses how older employees are viewed by their co-workers and if there are age-related differences in the attitudes towards older workers. Furthermore, we investigate if men and women experience forms of age and gender discrimination differently. To this end, this study draws upon a mixed method approach, consisting of qualitative focus groups and a large survey with over 1500 employees in three insurance companies. We find that stereotypes and age discrimination persist and differ between employees in their early, mid and late carer stages.