In recent years, there has been an immense preoccupation with Africa’s growing youth population. Despite the many concerns about this high youth population leading to high unemployment and under-employment, governments and tech firms see a large opportunity to absorb this young labor force into the ever-expanding digital economy. Large investments from philanthropic organizations like the Mastercard Foundation are going towards upskilling and training initiatives to prepare young African people for the tech-enabled future of work. However, more research is needed to understand the actual process of training young people. Using Kenya as the site of inquiry, this qualitative three-article dissertation examines interrelated aspects of training Kenyan young people to become Young, Gifted Africans who are prepared for the work in the digital economy. The first chapter uses systems thinking to draw a theoretical and empirical bridge between the sociology of organizations and the process whereby training and upskilling organizations produce Young, Gifted, Africans. The second chapter examines how Kenyan young people use digital platforms to present themselves as employable within the global workforce. The third chapter elucidates Kenyan young people’s relationship to entrepreneurship and draws distinctions between being an entrepreneur versus being entrepreneurial. This dissertation draws upon in-depth interviews, participant observation, and digital ethnography to assess the degree to which training and upskilling can really make tech-enabled jobs within the reach of Kenyan young people. This dissertation also provides insights on the stability and durability of an emerging Kenyan middle class. Lastly, this dissertation challenges assumptions the increasingly digitalized future of work will means Africa will be more equitably integrated into the global economy. Digitalization has a lot of potential for good, but truly understanding the needs and desires of African young people is the only way to prevent the reproduction of an extractive relationship between the Global North and Africa.