Smart City initiatives across the globe have spurred increasing demand for high-skilled workers. The digital transformation, one of the main building blocks of the Smart City movement, is calling for a workforce prepared to develop novel business processes. Problem-solving, critical and analytical thinking are now the essential skills being looked at by employees. The development of the so-called STEM curriculum, Science, Technology, Engineering, and Mathematics is being given a lot of attention by educational boards in response to preparing young generations for the Smart City work market. Based on the IMD Smart City Index, PISA, and World Bank reports, we develop a model for assessing the impact of the IT secondary school capacities on Smart-City business developments. The model reveals the relationship between the technological capacity of the secondary-school, and the business activity of a Smart City. Moreover, the study shows the existence of a positive relationship between the IT capacity of secondary schools and the resulting entrepreneurial activity of the city. Our results are of interest to decision-makers and stakeholders responsible for designing educational policies and agents involved in the digital transformation and development of Smart Cities initiatives.