This chapter outlines the technological evolution experimented by the Observatory for University Employability and Employment’s information system to become a data-driven technological ecosystem. This observatory collects data from more than 50 Spanish universities and their graduate students (bachelor’s degree, master’s degree) with the goal of measuring the factors that lead to students’ employability and employment. The goals pursued by the observatory need a strong technological support to gather, process, and disseminate the related data. The system that supports these tasks has evolved from a standard (traditional) information system to a data-driven ecosystem, which provides remarkable benefits covering the observatory’s requirements. The benefits, the foundations, and the way the data-driven ecosystem is built will be described throughout the chapter, as well as how the information obtained is exploited in order to provide insights about the employment and employability variables.