A machine for improving content delivery generates a graph representing a personalized conversational flow for sequenced delivery of digital content. The graph includes nodes representing interactive dialogues between a machine and a user, and edges that connect the nodes. The machine causes display of a user interface including a prompt related to job-seeking guidance. The machine, based on a first action in response to the prompt, dynamically adjusts the graph, the dynamic adjusting including selecting a first node. The machine generates and causes display of a first incentive content item, and a first call-to-action content item. The machine, in response to a second action received in response to the first call-to action content item, dynamically selects an edge connecting the first node and a further node. The dynamic selecting of the edge results in display of a further incentive content item, and a further call-to-action content item.