@Danny_Harrington, I too am looking for better functionality around this. I think this feature request (Add "People" custom field as variable assignee for rules) combined with @Bastien_Siebman’s tip above would make it possible for you to do what you want. Please vote on the feature. It would allow you to set roles in custom People fields and then create subtasks at certain points in your process that are assigned to the designated person in the People field. I hope the feature gets more momentum, as it would be a big leap forward in auto-delegation of work in flows. I am pleased they accomplished this with the date fields, allowing due dates to be set based on custom date fields. The ability to put people where we need them would be a much bigger win for us than dates.