Despite recent initiatives aimed at improving accessibility, the field of digital accessibility remains markedly behind contemporary advancements in the software industry as a large number of real world software and web applications continue to fall short of accessibility requirements. A persisting skills deficit within the existing technology workforce has been an enduring impediment, hindering organizations from delivering truly accessible software products. This, in turn, elevates the risk of isolating and excluding a substantial portion of potential users. In this paper, we report lessons learned from a training program for teaching digital accessibility using the Communities of Practice (CoP) framework to industry professionals. We recruited 66 participants from a large multi-national software company and assigned them to two groups: one participating in a CoP and the other using self-paced learning. We report experiences from designing the training program, conducting the actual training, and assessing the efficiency of the two approaches. Based on these findings, we provide recommendations for practitioners in Learning and Development teams and educators in designing accessibility courses for industry professionals.