Having recognized the positive impact of recent trends of technological developments on the rise of international activities of service sector companies (Vandermerwe and Chadwick, 1989), this chapter focuses on how the mode of entry correlates to the firm specifics. It also tries to address the particular characteristics of the service firm that define the necessity for a particular choice of strategy. We study to what extent and how the specifics of the home country and domestic market characteristics explain the international results of Russian IT companies. The theoretical framework is based on two main concepts. First is Dunning’s ownership, location, and internalization (OLI) paradigm that draws motivations for FDI. These are (i) resource-seeking investments aimed at accessing unique resources specific to foreign locations (e.g. natural resources), (ii) market-seeking investments aimed at entering new markets, (iii) efficiency-seeking investments pursuing an efficient specialization of firms, and (iv) st