Hi there, @subbud… if I understand your post correctly, it sounds like the app is behaving as expected given the setup you described, meaning the app can’t traverse past the direct reports level because that is the only level defined in your data structure.
As with all things Bubble, there are multiple ways you can go (for example, you could simply add a list field to the User data type that stores all of the users in a user’s chain of command), but here is one thing to keep in mind. There is a well-documented limitation of privacy rules where if you don’t have a direct relationship between a user and every user in their chain, you won’t be able to create a privacy rule that allows the “indirectly-associated” users to be found in searches.
Anyway, just some food for thought there, and I hope it helps.
Best…
Mike