Jackson is an English teacher, Spanish teacher, and school leader passionate about project-based and game-based learning. He has worked as a school designer for Institute of Play and was recently awarded an Innovation Grant from Facing History and Ourselves for the design of a tabletop card game "Empathy Builders" - a cooperative game that encourages players to take on other people's perspectives. He has written for "Principal Leadership" and has presented at the NASSP National Conference, ISTE, SXSWedu, the Facing History Partner Schools Network Conference, and with PBS Learning Media. Jackson is also a huge boardgaming enthusiast and evangelist.