Preheat oven to 350°F (175°C).
Set a 9- or 10-inch cast-iron skillet over medium-low heat. Melt the butter, then add brown sugar and salt. Stir with a wooden spoon for 1–2 minutes until the sugar dissolves and the mixture bubbles and looks glossy. Remove from heat and smooth evenly across the pan.
Peel the bananas and slice each in half lengthwise. Place cut-side down onto the caramel, packing them tightly to cover as much surface as possible. Fill gaps with small pieces.
In a medium bowl, whisk together flour, baking powder, baking soda, and salt.
In a large bowl, whisk together granulated sugar, eggs, buttermilk, oil, and vanilla until smooth.
Pour the dry ingredients into the wet ingredients and fold with a spatula until just combined. Do not overmix.
Pour the batter slowly and evenly over the banana layer and smooth the top.
Bake on the middle rack for 32–35 minutes, until the top is deep golden and a toothpick inserted in the center comes out clean.
Remove from oven and rest on a wire rack for exactly 5 minutes. Run a thin knife around the edges. Place a large lipped serving plate on top, grip firmly with oven mitts, and flip in one confident motion. Hold for 30 seconds, then lift the skillet. Reposition any bananas that stayed in the pan.
Serve warm with vanilla ice cream.