Place asparagus on a sheet tray. Lightly oil with 1 Tbsp. olive oil, season with salt and set aside.
Combine sliced tomatoes, sliced mozzarella balls in a small bowl. Toss with 1 Tbsp. Cherry pepper pesto. Season with salt & pepper, set aside.
Wisk 1/4 cup olive oil and remaining pesto in a small bowl. Set dressing aside.