Preheat & Prep. To start, preheat oven temperature to 350 degrees F. Lightly grease a 9x9 baking dish. (I prefer ceramic or glass pans for this pumpkin crisp.)
Combine Cream Cheese & Brown Sugar. In a large bowl, combine softened cream cheese and 1/2 cup brown sugar. Beat with a hand mixer until well blended and smooth. Scrape down the edges of the bowl.
Finish The Filling. Next, add pumpkin puree, maple syrup, eggs, 2 teaspoons vanilla, the spices, and 1/2 teaspoon salt. Mix on LOW speed until smooth and evenly blended. Scrape down the edges of the bowl. Pour the cream into the pumpkin mixture and mix on LOW speed until blended. Stir through with a spatula to make sure there are no hidden lumps or under-mixed sections. Pour filling into the baking dish.
Mix Up The Crumble Topping. In the same bowl (or a fresh one, if you don't mind extra dishes!), combine softened butter, gluten-free oats, brown sugar, gluten-free flour, pecans, 1 teaspoon vanilla, and pinch salt. Mix with a fork, a hand mixer, or your hands until the crumble topping is evenly mixed and there are large clusters. (There shouldn't be any dry spots left!)
Top The Crisp. Carefully add the crumble topping on top of the pumpkin filling, making sure to cover everything evenly and completely. (The better you distribute the topping, the more evenly this pumpkin crisp will bake!)
Bake pumpkin crisp in preheated oven for about 50-55 minutes until the top is golden brown and the filling has just a slight wobble in the center. I recommend setting a timer for the 40 minute mark. Check to make sure your topping isn't browning too quickly and loosely tent with foil if needed. (I don't need to tent this crisp in my oven, but you always want to check!)
Serve & Store. Cool the crisp at least 15-20 minutes before serving to allow everything to set. Serve with a scoop of vanilla ice cream or a dollop of whipped cream. (A drizzle of caramel sauce can also be incredible!) Cover any leftovers in the pan and refrigerate up to 3-4 days.