This chapter considers the link between productivity and wellbeing in the context of SMEs. The authors formulate a business–wellbeing–productivity framework, which connects business size and organisational structure with wellbeing parameters, which, in turn, are correlated with productivity. Using a country-level data set of Organisation for Economic Co-operation and Development (OECD) countries, we show that prevalence of SMEs in a country’s business sector is associated with the decrease in productivity of this country through SMEs’ negative impact on workforce wellbeing. Implications of this result for theory and practice are discussed.