In that dialogue entry ("You Win!"), set the Sequence field to:
When the conversation gets to this dialogue entry, it will activate the PopOut GameObject. The Delay command that you see after the semicolon tells the Dialogue System to keep the "You Win!" subtitle text onscreen for the regular amount of time.
I forgot to mention something earlier. The PopOut GameObject must be a child (or grandchild, etc.) of an active GameObject. It can't be a top-level GameObject in the Hierarchy. The SetActive() sequencer command isn't able to find inactive top-level GameObjects.