In a large bowl, using an electric mixer, beat cream cheese on high until fluffy, about 3 minutes. Add 1/2 cup maple syrup; beat until smooth. In a medium bowl, beat cream and sugar on high until soft peaks form, about 3 minutes. With a rubber spatula, stir about one-third the whipped cream into cream cheese mixture, then fold in remainder. Transfer to crust and refrigerate until firm, 3 hours (or up to 1 day).
Preheat oven to 450 degrees. Coat a parchment-lined rimmed baking sheet with cooking spray. Arrange pear slices in a single layer on sheet and brush with 2 tablespoons maple syrup. Roast until pears are soft, 20 minutes. Remove from oven and heat broiler. Brush pears with 2 tablespoons maple syrup and broil until browned in spots, about 4 minutes, rotating sheet frequently. Let cool. To serve, arrange pear slices, overlapping slightly, on cheesecake.