Prep: Once dough has proofed for about 1 ½ hours, it's time to shape it (dough should be hydrated and bubbly at this point). Coat a rimmed baking sheet OR 13x9-inch pan thoroughly with olive oil and place the dough in the pan, tossing to coat both sides in olive oil.
Stretch dough: Stretch and press dough gently into a rough rectangle about 1 inch thick.
Fill: Spread cooled jam evenly on top of dough. Don't spread it all the way to the edges - leave about an inch of space around all sides. Distribute brie evenly on top of jam.
Roll: Roll dough up into a log, starting with one of the short sides. Pinch the seams together to seal and place log seam-side down on the pan.
Re-stretch: Let the dough log rest about 10 minutes. Then gently stretch and press it back into a rough rectangle. It may break open a bit, revealing some of the jam inside. That's ok, but be careful not to tear it open too much.If you're having difficulty stretching the dough without breaking or the dough is bouncing back, let it rest another 10-15 minutes and try again. 2nd rise: Allow dough to rise again until very bubbly and airy, about an hour. Preheat oven to 425° F.
Dimple: Dimple the dough all over with your fingers, pushing all the way through the dough to the pan while being careful not to tear the dough.
Add toppings: Drizzle dough all over with 2 Tbsp olive oil. Sprinkle with ½ cup fresh raspberries, 2 ounces sliced brie, and 2 Tbsp coarse sugar.
Bake: Place bread in preheated oven and bake until golden brown on top and bottom, about 15-20 minutes. Internal temperature should be at least 190° F.