Okay so I first sent the Representative to a different settlement because he wasn't responding to me assigning him to a store. He still wouldn't go. So I sent him back to sanctuary and he still wouldn't accept me assigning him to a store. I'd just stand in front of the store with nothing happening.
Now he hands out radiant ai jobs (Go kill raider, ghouls, etc at some randome location). Problem is because this is a unique NPC, he doesn't seem to have any recorded lines for it, so he says nothing with some subtitles at the bottom saying what he was supposed to. As a result I get trapped in a never ending conversation until I pull away.