This study examines experimentation in the business modeling process, unpacking three different roles of experimentation: learning, signaling, and convincing. Learning is an inherent role of experimentation, as managers typically experiment to engage with the environment and to obtain knowledge. This study uncovers another set of roles, which have a symbolic nature. These roles show that experimentation is not just a learning process, but also a strategic legitimation process, aimed at enacting the environment. Experimentation serves the purpose of signaling to potential customers and other stakeholders, and of convincing them to embrace the business model. Furthermore, this study shows that experimentation takes two forms—purposeful interactions and experimental projects—and that these forms can support the different roles of experimentation.