Bourbon-Glazed Flank Steak with Chimichurri, Roasted Sweet Potatoes and Charred Broccolini

Prepare the bourbon glaze: In a small bowl, whisk together 1/3 cup bourbon, 3 tbsp brown sugar, 2 tbsp soy sauce, 1 tbsp Dijon mustard, and 1 minced garlic clove until sugar dissolves.

Place flank steak in a shallow dish and pour half the bourbon mixture over it, turning to coat. Reserve the remaining glaze for basting. Marinate at room temperature for 15 minutes while preparing other components.

Preheat oven to 425°F. Toss peeled and cubed sweet potatoes with 2 tbsp olive oil, 1 tsp smoked paprika, 1 tsp kosher salt, and 1/2 tsp black pepper on a baking sheet. Spread in a single layer.

Roast sweet potatoes for 25-30 minutes, stirring halfway through, until tender and caramelized.

While potatoes roast, prepare the chimichurri: Finely chop 1 cup parsley, 1/2 cup cilantro, and 2 tbsp oregano. Transfer to a bowl and add 2 minced garlic cloves, 3 tbsp red wine vinegar, 1/2 tsp red pepper flakes, juice of 1 lemon, 1/2 tsp salt, and 2 tbsp olive oil. Stir to combine and set aside.

Trim the ends of the broccolini. Toss with 1 tbsp olive oil and a pinch of salt and pepper.

Heat a large cast-iron skillet over high heat until smoking hot. Remove steak from marinade, pat dry with paper towels, and season with remaining salt and pepper.

Sear steak for 4-5 minutes per side for medium-rare (internal temperature of 130-135°F). During the last 2 minutes of cooking, brush with reserved bourbon glaze several times to create a caramelized crust.

Transfer steak to a cutting board and tent with foil. Let rest for 10 minutes.

While steak rests, use the same skillet to char the broccolini over medium-high heat for 4-5 minutes, turning occasionally, until tender-crisp with charred spots.

Slice the steak thinly against the grain at a 45-degree angle.

Serve sliced steak with roasted sweet potatoes and charred broccolini. Drizzle chimichurri sauce over the steak and vegetables.