Heat olive oil in a large skillet over medium heat, making sure the oil evenly coats the bottom of the pan. Add sliced onions to the pan, the liberally sprinkle with salt and pepper. Carefully stir ingredients together, then cook for about 20 minutes, stirring occasionally, until onions are soft.
Stir the brown sugar into the onions; mixture will become soggy. Reduce heat to medium-low and cook for 10-15 minutes, stirring often, until most of the moisture has evaporated and the onions appear dry.
Stir the balsamic vinegar into the onions. Reduce the heat to low and cook for 50-60 minutes, stirring occasionally, until most of the liquid has been absorbed and the onions are soft and dry.
Remove pan from heat and let onion jam cool. If desired, place onion jam in a small food processor and blitz for a few seconds until smooth.
Store jam in the refrigerator, but serve either warm or at room temperature.