In an increasingly fragmented and volatile political landscape, several studies point to the growing effect of executive candidates in determining citizens' vote. However, the rationales behind candidate selection remain mainly unexplored. This increasingly competitive environment may incentivize political parties to nominate electorally attractive people, regardless of their ideology of partisan background. This paper studies under which circumstances political parties are more likely to nominate political outsiders as executive candidates. Particularly, the role of intra-party institutions, the context of electoral competition and the role of incumbent Prime Ministers is assessed. These conditions are tested using a novel dataset on more than 2000 executive candidates in Canada, Germany, and Spain's sub-national level.