With warm steak and citrusy fruits, this salad will brighten up your menu.
Season the steak with salt and pepper. Heat a large skillet over medium-high. Add 1 tbsp. oil. Sear the steak, turning once, until medium-rare, about 5 minutes per side. Transfer the steak to a cutting board to rest.
Lower heat to medium and add the shallots to the skillet. Cook, stirring frequently, until the shallots soften, about 2 minutes. Transfer the shallots to the cutting board with the steak.
In a medium bowl, whisk the remaining 4 tbsp. oil with the sherry vinegar and paprika; season the dressing.
In a large bowl, toss the arugula, fennel, and half the dressing. Divide the salad among plates. Nestle the citrus into the salad. Season the citrus.
Thinly slice the steak against the grain. Top each salad with steak, shallots, and olives. Drizzle with the remaining dressing. Serve immediately.