Abstract: Various embodiments include a server system that parses a natural language text segment representative of a hierarchical checklist to generate a hierarchical workflow execution model. The hierarchical workflow execution model describes a plurality of task items corresponding to one or more line items in the natural language text segment. At least some of the task items can be respectively assigned to one or more participant roles according to the natural language text segment. Textual tokens of the line items can denote a hierarchical relationship structure of the task items. The server system can determine a logical constraint associated with enforcement of the task items based at least partly on the hierarchical relationship structure of the task items. The server system can enforce execution of at least a subset of the task items according to the determined logical constraint.