This document summarizes various experiments conducted by the city of Boston to engage citizens and make government more transparent and personalized. It describes experiments from 2008-2013 like Citizens Connect, City Worker, and Street Bump that aimed to connect citizens to government services via mobile apps, online chat, and collecting street condition data. The impact of these experiments included doubling service requests while maintaining delivery times, one third of cases now handled digitally, and an 89% recommendation rate from users, up 21% since starting these efforts. The document advocates that transparency, communication and personalization, if done right, can inform, empower and engage citizens.