The insurance market is going through revolutionary change - Internet of Things, Telematics and sensor technologies, Machine Learning (MA) with intelligent automation, growth of Cyber insurance, Big Data analytics and online ecosystems with cloud computing will significantly change the landscape of the insurance services market. In this paper, a multi-criteria decision-making methodology (MCDM), Analytical Hierarchical Process (AHP), is applied in the Latvian insurance market to assess the strategic decision making criteria. As soon as nowadays managers have high risk of contradiction in pairwise comparisons due to market dynamics and high level of uncertainty, the proposed evaluation model is based on the use of the consistency-driven linguistic methodology. The subject of the study is the influence of digitalization on customer preferences and development of Latvian insurance companies’ strategies. The purpose of this work is to study the development of insurance company strategies based on the shift of the perception values of clients, employees and owners of insurance companies in the era of digital transformation. According to the research results digital transformation is showing shift of customer perception values: simple product gives a greater benefit to the fact that owner only has to enter minimum information, so it is recommended to use smart-functions provided by digital opportunities to meet consumer's expectations. Within the scope of the survey, e-services perception values are mostly associated with the availability of product descriptions and comparison (aggregators), simple payment or online advisers.