The digital transformation of operation and maintenance (O&M) activities has been guiding the facilities management sector towards a strategic role focused on the performance of businesses and sustainable use of natural resources over assets’ lifecycles. Despite the application of information and communication technologies (ICTs), such as building information modelling (BIM) and the Internet of Things (IoT), demonstrating potential for improving such practices, evidence related to its implementation process from an FM professional’s perspective is still much needed to unlock billions of USD trapped in inefficient and fragmented processes. This research seeks such evidence by characterising current and potential applications of BIM and IoT-based solutions for FM, specifically on maintenance services. This exploratory research is based on a multiple case study where three universities’ FM sectors were investigated. Data collection and analysis included semi-structured interviews, focus groups, and inductive content analysis. By considering technology as a scaffold to enhance human activities, the investigation provided a deep understanding of technological, procedural, and policy issues in implementing BIM and IoT-based solutions in FM activities and their related benefits and limitations. Clarifying the necessary resources for such implementation could support FM sectors and organizations in justifying human and financial investments and planning the gradual digital transformation of services.