This article observes the theoretical issues concerning strategic sustainability of trading enterprises in the new conditions of economy digitalization. The need for digital control of the strategic sustainability within trading enterprises is explained. The article examines the contradictory nature of the current approaches to the most important categories of the strategic sustainability within the enterprises. Among them are stability, sustainability and competitiveness that hinder digitalization of the strategic management processes. This paper also proposes a new category of strategic sustainability which eliminates these contradictions within an enterprise based on the methodology of systemic dialectics and determining its nature. Various approaches to digital characteristics of the strategic sustainability within enterprises are considered together with their shortcomings associated with the lack or digital immeasurability of a whole range of elements. The article proposes a conceptual model for assessment of the strategic sustainability within the enterprises based on a set of digital components that most significantly affect it. The model stems from the synthesis of aspects typical for both the external and the internal environment of enterprises determining their strategic sustainability and the perspectives for their digitalization.