Preheat oven to 350°F. Generously grease a 10–12 cup bundt pan.
Mix granulated sugar with cinnamon in a large bowl.
Cut the cinnamon roll dough into 1-inch pieces.
Toss dough pieces in the cinnamon sugar until evenly coated.
Layer half the coated dough in the pan and sprinkle with pecans.
Whisk melted butter, brown sugar, and vanilla until glossy and combined.
Pour half the butter mixture over the dough, add remaining dough, then pour the rest on top.
Bake 30–35 minutes until puffed, deep golden, and the center is cooked through.
Cool 10 minutes, then invert onto a serving plate and remove the pan.
Beat powdered sugar, milk, and cream cheese until smooth; drizzle over warm bread.