Preheat the oven to 400°F (200°C). Line a rimmed baking sheet with parchment paper and let the dough rest according to the package directions until pliable.
Slice the sirloin thinly across the grain. Heat 1 teaspoon of olive oil in a large skillet over medium heat and sauté the onion and bell peppers for 6–8 minutes, until tender and some edges are golden.
Add the minced garlic during the final 30–60 seconds. Cook until fragrant, then transfer the vegetables to a bowl and allow excess liquid to evaporate from the skillet.
Add the remaining teaspoon of olive oil to the skillet. Sear the steak in batches over medium-high heat for approximately 2–4 minutes per batch, seasoning with Worcestershire sauce, oregano, smoked paprika, black pepper, and salt.
Return the vegetables to the pan, combine with the steak, and cook briefly. Remove from heat and let the filling cool for 5–10 minutes.
Roll the dough into a rectangle approximately 10 by 14 inches on a lightly floured surface, keeping the thickness even.
Spread the steak and vegetable mixture down the center, leaving a clean border around the edges. Arrange the provolone evenly over the filling.
Fold the long sides inward, roll the dough into a log, and pinch the seam and ends closed. Place the stromboli seam-side down on the baking sheet. Brush lightly with the optional olive oil and cut 3–4 small vents in the top.
Bake for 22–28 minutes, checking around 20 minutes, until the crust is golden and the dough is cooked through. Cover loosely with foil if the top browns too quickly.
Rest for 8–10 minutes, then slice into four portions with a serrated knife and serve warm.