Cities leaders recognize the need to invest in infrastructure and applications to improve their operations, the services they provide constituents, and the overall experience of their citizens. New internet-of-things (IoT)-enabled solutions and platforms offer a wealth of options and two distinct paths to building a smart city. Becoming smart, however, isn’t easy: City leaders must address the challenges of IoT-enabled initiatives to ensure success. This report offers guidance for I&O professionals on how to approach IoT-enabled initiatives and overcome potential challenges.