The theoretical relevance and practical importance of the development of hybrid organisations around the world has been experienced, among others, by the post-communist economies. The trend towards emerging hybridisation in the transitional economies of Central and Eastern Europe (CEE) has grown significantly in recent years. The process of spanning sectoral boundaries (Billis, 2010; Dees and Anderson, 2003; Laville and Nyssens, 2001) is ‘now perhaps accelerating’ (Donnelly-Cox, 2015), especially with the development of social enterprises that seem to transcend sectors (Dees and Anderson, 2003). To date, however, we lack the means of reflecting in detail on the specific nature of hybridity in a transitional context as well as on the kinds of current public debates and policy-making discourses within which it takes place. This chapter intends to try to fill this gap. The chapter does not attempt to do justice to the considerable heterogeneity of transitional economies but focuses on the Czech Republic in an attempt to present a comprehensive picture of the way in which civil society was transformed in this one country. From the early years of the transition from communist rule, public services were seen as being delivered by hybrid organisations operating in the intersection of the market, the civil society and the public sector.