Despite the economic and societal significance of microbusinesses (MBs), digital transformation (DT) efforts in the MB sector have been rather sporadic. Further, prior DT studies have primarily examined large- and mid-sized organisations, leaving a perceptible void in the literature. In this paper, we leverage the unique context of MBs and recognise the key role of microbusiness owner-managers (MBOMs) for the management and sustenance of DT initiatives. Specifically, we theorise the influence of MBOMs’ DT readiness in terms of their growth and technology mindsets contributing to their DT learning resources and processes. Drawing on qualitative data from a series of structured interviews and focus groups with MBOMs and other key stakeholders in the Irish MB digital ecosystem, we identity three MBOM digital transformer archetypes comprising unique configurations of MBOMs’ growth and technology mindsets, namely: champion digital transformers, emerging digital transformers, and aspiring digital transformers. For each of these archetypes, we explore the different learning capabilities and mechanisms through which MBOMs manage and sustain their digital transformation efforts. Our findings offer theoretical contributions to the fields of digital transformation in microbusinesses, digital leadership, and digital capabilities. Our study also has significant implications for policy and practice.