Combine the Rosemary leaves, Pepper and Olive oil in a blender and blend finely but don't turn it into a smoothie. You should see little bits of Rosemary leaves in the mix.
Wash the Tri-Tip with warm water, then dry it with a paper towel. This step helps the Rosemary sauce soak into the meat.
Brush the Rosemary sauce onto the Tri-Tip with a brush working it into the meat fibers where you can. Layer it on thick.
Wrap the entire roast tightly in plastic wrap. Remove any air bubbles along the way.
Place in the refrigerator and let the Rosemary sauce soak into the Tri-Tip roast.
Place the Tri-Tip on a hot grill set to medium-low heat. The outside Rosemary will get burned and the Tri-Tip will darken, this is normal. Grilling time roughly depends on your grill, if you cook with the lid down or up, and the thickness of the Tri-Tip. Use a meat thermometer or test the meat by cutting into it once the outside is darkening.
Use LOW-MEDIUM heat, anything hotter will burn the outside too much and not cook the inside enough.
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