Education is increasingly enhanced by technology, and at the same time, the rapid pace of technology innovation and growing demand of consumers introduces challenges for providers of technological learning solutions. This paper investigates Finnish small and medium size companies who either develop or deliver technological solutions for education. Twelve companies were interviewed in order to capture the entrepreneurial narratives of successful design of learning solutions. Data was analyzed based on a conceptual framework. The framework draws on the situation awareness concept, meaning that we seek to answer the question how the participant enterprises examine relevant elements in their environment with regard to their development process. The results show that all the mature companies included in the study have well balanced situation awareness, but amongst the incubating and accelerating enterprises, balanced profiles are rare.