Many organizations today require continuous development and effective learning processes to meet the challenges of globalization and digitalization. In this seven-year study, we investigate a learning practice as an integrated part of work in a global IT company on their way to act more knowledgeable and effective world-wide. We aim to develop a middle-range theory for learning from experience in the context of work by utilizing qualitative case study research as methodology for the vast amount of data including a thick description of the seven year development. The middle-range theory is suggested as an organizational learning spiral that considers critical ontological dimensions as well as critical starting points for how and when such an intermediate model might be applicable. We hope to contribute to research on learning in the context of work and further research is needed in order to determine the usefulness of this middle-range theory.