This research provides new theoretical and empirical insights into the gender politics of the springboards to chief executive office. The extremely masculinised composition of the relatively few top national executive positions has posed a serious impediment to empirically assessing the conditions that may facilitate women's under‐representation and men's over‐representation. To overcome this constraint, this study looks at the top regional executive office across four West European countries that present a multilevel state structure – namely Austria, Germany, Spain and the United Kingdom. Using two original datasets, the article examines the ways in which the selection and reselection of regional prime ministerial candidates is shaped by individual, organisational and institutional factors that produce heterogeneous experiences and career opportunities across sex. The results show that women have not shattered the glass ceiling at the regional level and pinpoint the fact that they are held to higher standards, benefit less from the political resources they possess and are more dependent on the decision environment in which parties select executive candidates. The conclusion is that the rules of the game guiding selection and reselection processes are strongly biased towards men.