Desklight worked with stakeholders to conduct design research in select Chicago Public Schools. What became evident in this research was that teachers were hungry for ways to improve their own development, which would ultimately make for better teaching performance and improve learning outcomes for students. What was evident early on was that there existed a way to meet that design challenge and promote the sharing of ideas and best practices through the development of a digital matchmaking and reflection tool strategy where teachers could communicate with and support one another throughout the system.