This work conceptualizes an integrated real-time management and dynamic optimization system for earthwork fleets, based on recent technological developments with potential to track and improve productivity in transportation infrastructure construction processes, namely real-time monitoring and modern optimization technologies. The combination of monitoring and dynamic optimization technologies features the potential to tackle the elevated uncertainty and volatility inherent to the earthworks environment, not only by providing the necessary flexibility and adaptability to an optimization system, but also by integrating equipment, processes and design in a real-time decision support context. Ultimately, this combination can comprise a foundation for development towards the automated, interconnected cyber-physical systems of Industry 4.0.