The article is an attempt to provide argument towards the need to rethink changes in the management framework of a business entity associated primarily with modern manifestations of competition and the lack of an effective competitive environment, as well as weak competitive edge and poor innovation capacity. Based on the Medigran company, the study explores key stages of competitiveness development in small businesses along with suggesting the following successive development phases: basic financial planning, forecast-based planning, planning focused on the external environment, strategic management, company internal monitoring. The hypothesis of the study is to offer insights and evaluate competitiveness development stages as well as efforts to its enhancing subject to the external and internal environment specifics. The purpose of the study is to explore the nature and assess the Medigran competitiveness, and to identify its core advantages to gain the company competitiveness in modern business settings. An in-depth analysis of management practices has enabled to identify an effective tool to manage the Medigran’s competitiveness based on the use of a situational approach. It is argued that successful implementation of administrative technologies in the context of strategic management of the company competitiveness, sales boosting policies, developing technical support, and creating competitive advantages will ultimately provide a synergistic effect. The findings demonstrate that to gain sustainable competitive advantages, it is critical to identify their priority sources, create promising opportunities, add value and build new fundamental competencies, as well as employ benchmarking, overcome organizational inertia, timely detect and update outdated knowledge, skills and processes.