The software industry in Brazil, although considered within the priority and strategic government policies to encourage the sector, has presented difficulties to stand in the international arena. However, some companies stand out, creating attention on the process of evolution of internationalization of these firms in both academic and business arenas. In order to investigate this fact, the scope of this study was to analyze the trend of internationalization of a leading software company in Brazil, being selected for such the company Totvs. The study included a literature review, presenting recent theoretical developments concerning the internationalization of companies, including two theories of internationalization: the Uppsala Theory and the Theory of International Entrepreneurship. The method chosen to implement the survey was the case study, having used primary data (interviews) and secondary data (book about the company, information from the Internet, press reports and company documents). The results indicated that the success of the internationalization strategy of Totvs is tied primarily to two factors: (i) the entrepreneurial characteristics of its directors and (ii) not by chance, the rapid strategic movement towards internationalization done by the company when it came across environmental changes in the local economy (in particular, the opening of the market to international competition). The study also points out that although Totvs have started the process in a loosely structured way, the company was able to learn from mistakes and over time have created a successful process of entry choice into other countries.