Preheat the oven to 375 degrees. Line a baking sheet with parchment paper.
In a large bowl, combine the ground beef, breadcrumbs, egg, Italian seasoning, salt, and pepper. Mix until just blended.
Press half the meat mixture into a loaf shape on the prepared baking sheet. Spread the pesto evenly over this layer.
Cover the pesto with the remaining meat mixture and seal the edges. Sprinkle the mozzarella cheese over the top.
Toss the asparagus with olive oil, salt, and pepper on the same baking sheet around the meatloaf.
Bake for 45 minutes until the meatloaf reaches 160 degrees internally and the asparagus is tender. Let the meatloaf rest 5 minutes before slicing.