Blended learning usually refers to the combination of online/offline instructional methods. In this paper, we describe a university course in “E-learning Psychology” designed to blend not only modes of teaching, tools, and media, but also learning contexts; specifically, academic and professional contexts. To achieve an effective blend of learning contexts, students were monitored by academic and company tutors through an instant messaging app (WhatsApp). The unique contribution of the company tutor to the blending of academic and professional contexts is explored. By qualitatively analyzing (i) process data (four WhatsApp log chats) and (ii) self-report data (interviews with six company tutors), we found that the company tutor contributed to both the traditional blended dimension (mixing online and offline) and to the blend of the academic and professional contexts. When company tutors participated in the chat, students moved from an organizational dynamic, featuring chats monitored by only the academic tutor, toward a more collaborative and reflective dynamic. The company tutors considered the opportunity to blend academic and professional contexts as the best aspect of the course for both themselves as educators/company representatives, and for the students. This paper offers insights into the ongoing discussion about what blended is—or should be—and the role of company tutors in blending educational contexts.