Project-based firms increasingly rely on digital tools to manage complex projects throughout project lifecycles. Some digitalisation efforts may fail, as they do not to account for differences in how experts and managers in various professional roles experience and adopt these tools. This study examines how a learning solution can be designed to address differing digitalisation awareness and role-relevant knowledge needs in project-based firms among engineers/designers, supervisors, and managers. Using an Action Design Research approach, we develop, implement, and evaluate a modular, role-sensitive learning solution in the context of European project-based firms in shipbuilding. The learning solution consists of a common learning module combined with role-specific modules tailored to engineers/designers, supervisors and managers. Iterative design cycles involved data collection through semi-structured interviews, a learning-preferences survey, a structured workshop, successive expert evaluations, and iterative piloting and refinement of the learning solution. The findings demonstrate that role-sensitive learning design enhances perceived relevance, clarity, and readiness to adopt digital tools across user groups. The study contributes design principles for developing learning solutions that support digitalisation, data-driven tool awareness, role-relevant knowledge, and readiness to adopt digital tools in complex project-based environments.