Preheat the oven to 375°F. Line a sheet tray with foil and place a wire rack on top. Set aside.
In a small saucepan whisk together the maple syrup, dijon, brown sugar, vinegar, garlic, salt, and pepper until smooth. Place over medium-low heat and bring it to a simmer, stirring occasionally. Let it simmer for about 10 minutes, stirring occasionally, until the glaze coats the back of a spoon. You know it’s thick enough when you run your finger over the spoon and the glaze does not drip (be extremely careful if you try this method, HOT!).
Pat the pork tenderloins dry with a paper towel.
Season on all sides with salt and pepper. In a large skillet (I like to use cast iron) over medium-high heat, add the oil and sear the tenderloins on all sides until golden brown. This will only take a minute or so on each side.
Place the pork tenderloins on the wire rack that is on top of the sheet tray.
Brush the glaze all over the pork tenderloins and roast for 10 minutes. Brush again with the glaze, roast for an additional 5 minutes. Brush again with the glaze, by now you should have used it all, continue to roast for another 5 minutes or until the internal temperature reaches 145°F, or to your preferred temperature.
Take the tray out of the oven and let the tenderloins rest for at least 10 minutes, you can cover them with foil if you are concerned they might cool off too much.
Slice against the grain and serve.