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The article attempts to present the evolution of generations of people of the 20th and 21st centuries through the prism of economic, institutional and professional substantive peculiarities. The professional qualities and features of each generation’s training are specified. The skills of the classical employees of the baby boomer generation are generalized and compared; the contents of the new progressive skills inherent in the digital generation are disclosed. The authors specify the economic and organizational benefits for the company from the work of digital specialists, including the following: ability to scale the business; increase in income; exit from the routine without having to check every action of employee. The professional flexible/soft skills of a digital person gaining knowledge at an innovative-entrepreneurial university are defined as follows: ability to effectively communicate with the surrounding; emotional intelligence; time management; flexibility and creativity; stress resilience. It is reasoned that there is an urgent need for the all-round advance with regard to equipping and providing with the most recent capabilities for every employee in their digital workplace. The benefits of a digital workplace for a generation of millenials, buzzers, and alpha people are presented via the prism of the matrix structure of advantage of the Office 365 along with the challenges it poses. It is concluded that the innovation-entrepreneurial universities are exclusive in producing innovations, educating active and progressive youth, entrepreneurs. The economic vocational education gained by the generation of digital people at an innovative-entrepreneurial university will cause influence on: salaries of developers; presence of high-level professionals in the labor market; transparency of the rules for selecting IT companies as contractors, etc.