How to Make It
Preheat oven to 375°F. In a medium bowl, toss the squash with several grinds black pepper, 2 tablespoons oil, and ½ teaspoon salt.
Combine pepitas, butter, sugar, maple syrup, and ½ teaspoon salt in a small saucepan over medium heat. Stir until butter melts, then bring to boil. Reduce heat and simmer until glossy and thickened, about 1 minute. Pour into the bottom of 8-inch square or other 2-quart baking dish and swirl to cover sides. Top with 1 tablespoon thyme leaves, then squash. Drizzle with 1 tablespoon oil. Place in freezer while preparing buns.
Unroll one can of crescent roll dough on a lightly-floured surface. Pinch together any seams so that you have a smooth rectangle with no holes. Flip the dough over and repeat. Brush dough with 1 tablespoon oil and top with several grinds black pepper, 1 teaspoon chopped thyme, and ¼ teaspoon salt. Starting with the short end nearest to you, roll the dough into a log and place seam-side down. Slice crosswise into 8 rounds and place on top of squash in baking dish. Repeat with second can of crescent rolls, olive oil, pepper, thyme, and salt, arranging the rolls on top of the squash so they are evenly spaced.
Bake until golden brown, 25 to 30 minutes. Let cool for 10 minutes, then invert onto a large serving platter. Top with flaky salt. Serve warm.