This study provides a framework for the comparative assessment of the key industry aspects of competitiveness among logistics services and the logistics systems of enterprises in the informational environment. Frequently, the relationships between a consumer and a company created by means of the informational environment determine how the enterprise positions itself in the market. For instance, the evaluation of a company’s representation in the information field is an essential aspect of determining the company’s competitiveness. The study suggests a set of special metrics for measuring the representation of digital components and other aspects of an enterprise’s digital image via data gathering and analysis of the most encountered tokens. The proposed automated analysis algorithm allows companies to examine their image in the digital environment and implement effective decisions. The functionality of the algorithm fosters data collection, helping to form the desired image of the company. Tokens of several thematic groups on social media are collected during the process, and the most significant of them that are valuable for the competitiveness of the enterprise are extracted. The outcome can be used for the tracking of the dynamics of key parameters of an enterprise’s image and for conducting a comparative analysis of the digital image of its competitors.