The activities of an enterprise are based on constant exchanges of material and nonmaterial goods with its stakeholders. According to the stakeholder concept, there are common features in the processes of enterprise’s interaction with different groups of stakeholders. For example, common patterns can be found in the behavior of two primary stakeholders groups – buyers and employees. Each actor of these stakeholder groups makes a choice between enterprises on the bases of characteristics of goods (products or working conditions), which are provided by these enterprises, and their own preferences for these characteristics. And yet the preferences of different actors from one stakeholders group are generally different. For example, different buyers have different preferences about products characteristics, and employees have different preferences about working conditions. Thus, in the market of certain good (products or vacancies), on the one hand, there is a variety of variants of the good which differ in their characteristics and, on the other hand, there is a variety of subgroups of stakeholders (buyers or jobseekers), which differ in their preferences about the characteristics of the analyzed good. Therefore, the demand for the good offered by the analyzed enterprise depends on the ratio between the supply of the analyzed good variants and the demand for them from stakeholders subgroups with different preferences. This fact should be taken into account in the process of analyzing and forecasting demand for products and vacancies of enterprises, but existing demand models do not take it into account. The purpose of the study is to construct mathematical models that will allow to assess the demand for products and vacancies of an enterprise, depending on: а) characteristics of the analyzed products and working conditions; b) the preferences of the stakeholders for these characteristics values; c) the available supply volumes from competing enterprises. The paper proposes to assess the demand for an enterprise products by means of an optimization “transportation” model, in which the variables are the volumes of the distribution of variants of products, which differ in consumer characteristics, between groups of buyers, which differ in preferences for products characteristics. Similarly, the demand for vacancies of an enterprise is proposed to be evaluated using the system of optimization "transportation" models, in which the variables are the volumes of the distribution of vacancies in different enterprises, which differ in working conditions, between groups of jobseekers, which differ in the level of competence and preferences for the characteristics of working conditions. The constructed models are designed to meet the challenges of analysis and modeling enterprises activity, taking into account the existence of different variants of buyers’ and employees’ preferences. The novelty of the proposed models resulted from taking into account the set of variants of stakeholders' preferences for the characteristics of goods, as well as using the criterion that evaluates variants of goods distribution among stakeholders in the context of its matching for the preferences of different sub-groups of stakeholders.