How to Make It
Preheat oven to 350°F. Grease a 9-inch square baking pan with baking spray, and line bottom and side with parchment paper.
Beat together butter, brown sugar, and 3/4 cup of the granulated sugar in the bowl of an electric stand mixer fitted with paddle attachment until smooth and creamy, about 1 minute. Add eggs, 1 at a time, beating just until blended. Add vanilla, and beat until combined.
Whisk together flour, baking powder, baking soda, and salt in a large bowl until combined. Gradually add flour mixture to butter mixture, and beat until combined.
Divide dough in half. Stir chocolate chips into 1 of the halves. Transfer chocolate chip half to bottom of prepared pan, and press into an even layer. Top with jam; spread into an even layer. Top with remaining half of dough, and press into an even layer.
Stir together cinnamon and remaining 1/4 cup granulated sugar in a small bowl; sprinkle on top of dough. Bake in preheated oven until top is golden brown, and edges are browned, about 45 minutes, covering with aluminum foil the last 15 minutes to prevent the top from browning. Cool on wire rack until fully cooled before slicing, about 1 hour.