Embodiments of the invention are directed to a fleet management system that assists with management and monitoring fleets of powered machines and their operators, such as fleets engaged in landscaping, grounds care, and forestry service. In this regard, embodiments of the invention are directed to systems and methods for automatically gathering data about one or more pieces of outdoor power equipment and one or more human operators of the equipment, processing the data into more useful data and data formats, and providing useful feedback, data, and tools to users of the system via, for example, a web portal that either assists users with management of a fleet of equipment and operators or provides useful information to owner-operators of outdoor power equipment about their performance and their machines.