Sauté sausage in a small nonstick skillet over medium heat 5 minutes or until crispy. Drain on paper towels, and cool. Drain pimiento; reserve 1 Tbsp pimiento. Process Cheddar cheese, mayonnaise, buttermilk, hot sauce, kosher salt, freshly ground black pepper, and remaining pimiento in a food processor or blender 20 to 30 seconds or until smooth. Add reserved 1 Tbsp. pimiento, and pulse 2 times or just until blended. (Mixture should be slightly chunky.) Place lettuce wedges, cut sides up, on plates, and drizzle with pimiento cheese dressing. Top each wedge with diced sausage and 1/4 cup cherry tomatoes, halved.