Sidekick is an app that provides math-in-context projects for high school classrooms. Our projects are all based in the real-world and are extracted from real problems of existing organizations (governments, companies and non-profits). As a bonus, students working on our projects get to interact with people from these organizations and present their findings to a panel of staff. This boosts engagement and hence learning. Sidekick is enabled by machine learning technology that allows us to quickly convert simple project briefs from partner organizations into classroom-ready lesson plans, or as we call them Project Handbooks. These documents give teachers information about standards, student activities, assessments, and partner contact information, enabling them to run these projects in class easily.