The article presents the results of a study of the impact of the following two factors — digitalization and crosssegment financial convergence — on an insurer’s client-oriented strategy. Authors formulated the modern notion of “customer-oriented strategy of insurer” based on the current level of using various Internet resources by the population of Russia. The influence of these factors on the real customer-oriented strategy of the insurer was assessed by the extent to which each of the factors ensured the fulfillment of insurance services consumers’ preferences and requirements included in the new content of the insurer’s customer-oriented strategy. It is shown that at present, the influence of both factors does not fully ensure the fulfillment of these preferences and requirements. The authors justified the position according to which the implementation of the modern content of the client-oriented strategy of the insurer is possible within the framework of cross-sector financial convergence, in which IT platforms and networks are the basis for doing business.