Do different institutional arrangements systematically influence political profiles of executive chiefs? To investigate this question, we employ a comparative analysis of heads of regional executives in two countries with similar political, economic and social development, namely, the Czech Republic and Slovakia. Regional self-governments were introduced in the two countries only in the process of their accession to the European Union, and the first regional elections were held in 2000 and 2001, respectively. However, regional political subsystems differ considerably: In Slovakia, župans operate under system of separation of powers, are directly elected in a majoritarian system with runoff, and are not responsible to regional assemblies. In the Czech Republic hejtmans are elected by the regional assemblies, normally rely on support of a stable coalition of parties, and can be removed from office in a no confidence motion. We hypothesize that different institutional incentives lead to selection of regional executive chiefs who differ systematically in the two cases. Specifically, we focus on three dimensions of their political profiles: party organizational dimension (their membership and leading role in their political parties), the political career dimension (i.e. patterns of their political careers prior to assuming regional executive office) and the expertise dimension (previous occupation, education and work experience). To corroborate our initial hypotheses, we examine seventy-two Czech regional chief executives and their thirty-two Slovak counterparts, i.e. all officials heading regional self-governments in the two cases. We look at mandates rather than office holders in order to allow for analytical flexibility in assessing changes in the previous career paths. Thus, in our research design, political profiles of executive chiefs are treated as dependent variables, while institutional setting, namely type of elections and “executive-legislative” relations serve as explanatory variables.