Preheat oven to 425F.
Peel and dice the butternut squash into cubes. Toss with 1 Tbsp olive oil and 1/4 tsp. salt and spread evenly over parchment lined baking sheet.
Bake squash for 40-45 minutes, until fork tender and browning.
While squash is baking, make the pesto. Heat a skillet over medium low heat and add the pumpkin seeds. Toast, stirring occasionally, until seeds are fragrant and beginning to golden. This takes about 5-10 minutes. Remove from heat and let cool for 10 minutes.
In a blender, add the basil, 1/2 cup olive oil, garlic olive oil or garlic cloves and roughly blend until basil is broken down. Add 1/2 a cup of the pumpkin seeds and 1/4 tsp. salt and pulse into you have a rough pesto texture. Taste and add more salt as needed.
Once butternut squash is cooked, let cool for 5 minutes before tossing with the pesto in a large bowl. Sprinkle with remaining 1/4 cup pumpkin seeds and serve.