The need to break down the barriers facing women in the labour market arouses great interest for reasons of social and sustainability justice. This study breaks new ground on the topic of the “glass ceiling” by assessing the evolution of gender inequality in the proportion of individuals reaching high managerial positions. The application of the csQCA method to a survey of two cohorts of Spanish graduates in management sharing the same starting conditions reveals two factors: job variety and additional education, as conditions that are usually present in a successful managerial career. Our findings confirm the prevalence of the gender gap with little progress in recent years. Women find it more difficult to promote to high managerial positions whereas being a man turns out to almost be a guarantee for eluding low managerial positions. In the context of Spain, and for sure in most other countries, the few women attaining high managerial positions still need to make a greater effort in their professional career than their male counterparts.