Manufacturing small and medium enterprises (SMEs) are recognized as a major driving force in European Union (EU) and elsewhere both economically as well as technologically in this ever-changing manufacturing paradigm. SMEs have major difficulties in implementing digital technologies such as the industrial internet enabled technologies that can lead towards a change in the business models, especially towards pay-per-output type business models. In this paper, we have studied pioneering manufacturing SMEs that have implemented pay-per-output business models as well as the related advanced automation systems. Both case companies were able to demonstrate the benefits and difficulties that they faced because of the size (SME) during the implementation process of both the pay-per-output business model and the related advanced automation system.