Heat a large cast iron skillet (or other oven safe pan as desired) to medium-high heat on the stove. Add olive oil, and once olive oil gets hot and begins to smoke, add the tri tip to the pan (fat side down, if the fat cap is still on the tri tip steak).

Sear for 3 minutes per 2 lbs, without moving. Take a peek to make sure the bottom is completely browned and seared, then use tongs to sear the edges of the tri tip for about 20 seconds each, until lightly browned (against the pan for 20 seconds each side. Place the uncooked flat side of the tri tip down on the pan. Turn off the burner.

Transfer skillet seared tri tip to the oven to bake at 425°F for about 12 minutes per pound. Exact time of how long to cook tri tip in the oven will vary based on your desired steak temperature. For best results, use a thermometer that has a probe that reads the temperature of the steak while it cooks in the oven so you know exactly when the inside temperature reaches your desired level of doneness.