In a small trifle or baking dish, assemble dip: Add guacamole to base and top with 1/2 cup ranch. Top with a layer of rotisserie chicken, then top with 1 cup tomatoes. Top with 1 1/2 cups cheddar, then add romaine and cooked bacon.
Top with remaining cherry tomatoes and cheddar and drizzle with ranch. Garnish with chives and season with pepper.