Preheat your oven to 400 degrees Fahrenheit. Add the goat cheese, cream cheese, Monterey jack, and garlic powder to a food processor.
Puree until smoothish, around 30 seconds.
Brush a baking dish with olive oil, then add the cheese mixture.
Add the tomatoes to a bowl and drizzle with olive oil. Add a few pinches of salt and pepper (optional), and toss until the tomatoes are well coated.
Add tomatoes and bake for 40 minutes. You want the tomatoes to be near bursting/burst before you remove it from the oven.
Remove the dip from the oven and serve while it’s hot and bubbly. Enjoy!