Local governments are seeking effective ways to promote sustainable commuting for reducing energy consumption and improving commuters’ experience. They often use so-called “Workplace Travel Plans” as policy interventions to engage work organizations as active players, promoting sustainable commuting amongst their employees. However, it remains difficult to systematically engage work organizations and commuters in such efforts for a number of reasons, ranging from preferences to constraints that they have to deal with. We aim at providing commuters, work organizations, and public administrators with tools that facilitate this engagement. In this paper, we discuss the requirements for the design of technology supporting corresponding services for commuters and work organizations. We also outline the comparative work we are aiming to do to understand how Western requirement differ from countries like India.