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The internationalization process in recent decades has been discussed from different approaches. In this chapter, we study the evolution of selected Latin American and Spanish companies that have experienced a growing evolution from small or medium-sized enterprises to large corporations with participation in global markets and a strategic role played by the family organizations and small business groups. It is a study of multiple cases scope focused on two main lines of discussion. In one hand, the trajectories of internationalization and, and the other, the family firm organization and structure, correspondingly to sectorial aspects and the global situations that have encouraged the expansion of markets, the acquisitions of assets outside the countries of origin, and the outsourcing system. The group of companies selected to discuss the heterogeneity of the internationalization processes is based in case studies: Lojas Amerianas-Brazil, Crystal Lagoons-Chile, Despegar.com-Argentina, Sol-Meliá, Spain, Ferrovial, Spain, Talgo, Spain. Among the findings of this comparative study, the following stand out: (1) debates about the family business are alive, (2) multidimensional perspectives between countries are needed to understand not only internationalization but also the relevance of competitive learning, entrepreneurial vision evolution, and diversity of trajectories between sectors and companies, and finally (3) the importance of culture and immigration in business and family development from Small and Medium Enterprises (hereafter SME) to large businesses.