Burrito Butternut Squash Boats

Name: Burrito Butternut Squash Boats
Ingredients: 2 small butternut squash, halved and seeds removed; Extra-virgin olive oil; Kosher salt; Freshly ground black pepper; 1 large onion, chopped; 3 cloves garlic, minced; 1 lb. organic grass fed ground beef; 1 tsp. ground cumin; 1/2 tsp. chili powder; 2 ears sweet corn, kernels removed (about 1 1/2 cups); 1 (15.5-oz.) can black beans, drained; 1 (10-oz.) can enchilada sauce; 1 1/2 c. shredded Monterey jack; 1/2 c. quartered cherry tomatoes; Freshly chopped cilantro, for garnish (optional)