Condensation is a phase change phenomenon often encountered in nature, as well as used in industry for applications including power generation, thermal management, desalination, and environmental control. For the past eight decades, researchers have focused on creating surfaces allowing condensed droplets to be easily removed by gravity for enhanced heat transfer performance. Recent advancements in nanofabrication have enabled increased control of surface structuring for the development of superhydrophobic surfaces with even higher droplet mobility and, in some cases, coalescence-induced droplet jumping. Here, we provide a review of new insights gained to tailor superhydrophobic surfaces for enhanced condensation heat transfer considering the role of surface structure, nucleation density, droplet morphology, and droplet dynamics. Furthermore, we identify challenges and new opportunities to advance these surfaces for broad implementation in thermofluidic systems.