Osterweil is a creative consultant to The Education Arcade and a research scientist in the MIT Comparative Media Studies/Writing Program. As a game designer he has worked in both academic and commercial environments, and his work focuses on the authentically playful aspects of challenging academic subjects. He has designed games for computers, handheld devices, and multiplayer online environments. He is the co-creator of the acclaimed Zoombinis series of math and logic games and has lead a number of projects in The Education Arcade, including the MIT/Smithsonian-curated game, Vanished (environmental science); Labyrinth (math); Kids Survey Network (data and statistics); Caduceus (medical science); iCue (history and civics); and the Hewlett Foundation’s Open Language Learning Initiative (ESL).  He is a founding member of the Learning Games Network, where among other projects he created Quandary (ethics), the 2013 Games 4 Change Festival game of the year.