Electronic document generation systems and methods include a processor, a memory component communicatively coupled to the processor, and machine-readable instructions. The machine-readable instructions cause the system to access an electronic document generation template including placeholders with nesting values indicative of a number populating conditions to generate an electronic document, populate one or more placeholders associated with corresponding nesting values of zero with data from a master data store or data that is based on a user input to a prompt, prompt, via a graphical user interface, the user to respond to one or more conditional prompts, populate one or more placeholders associated with the next lowest corresponding nesting value based on a user input to the one or more conditional prompts, and generate the electronic document based on the one or more placeholders as populated via the electronic document generation template for display on the graphical user interface.