Preheat oven to 375 degrees.
Combine pears, orange zest, orange juice, vanilla, cinnamon, salt, dark brown sugar and flour in a large bowl.
Melt butter in a 10-inch oven-proof skillet and cook until it turns brown and smells nutty. Pour into the pear mixture and toss to combine, then transfer back to the skillet.
Arrange the puff pastry squares over the top to cover most, but not all of the filling. It's okay for parts of the pear mixture to poke through. Brush the pastry with egg wash, then sprinkle lightly with coarse or granulated sugar.
Bake until puffed and golden, about 30 minutes. Pour heavy cream all over, then return to the oven for 10 minutes. Remove from the oven, then use a spoon to press the pieces of puff pastry down so the juices ooze over top. Place back in the oven for an additional 10-15 minutes or until the crust is crisp and very dark brown.
Let cool, then serve warm with vanilla ice cream.