The progress in context-aware systems is predominantly technology-driven, leading to innovations in technology- savvy industries while having almost no impact on other industries, such as the insurance sector. In this paper we introduce a novel, key player-oriented framework that explicitly takes into account the (business) value for each player being relevant when implementing a particular context-aware service on the market. We illustrate the framework’s applicability by means of a case study of a context-aware system that allows for monitoring high-value items for insurance purposes.