Systems for and methods of generating an executive summary by monitoring checkpoints in structured data. A system includes a computing device having a memory and at least a processor communicatively connected to the memory, wherein the memory contains instructions configuring the at least a processor to retrieve event data associated with a project, identify at least a checkpoint as a function of the event data, monitor a progress relative to the at least a checkpoint, generate a recommended course of action as a function of the progress indication, generate an executive summary, and route the executive summary to at least a target entity as a function of routing logic associated with the project.