Rub steak on both sides with olive oil and season with salt and pepper. Let sit at room temperature 30 minutes.
While steak sits, make the salsa: Brush sweet corn with 1 tablespoon olive oil and rub remaining olive oil over red pepper halves.
Grill corn and peppers over medium-high heat, turning occasionally until veggies are slightly charred and cooked through. Remove from grill and remove corn from cob and chop red pepper finely.
Combine charred corn and pepper, jalapeno, lime juice, cilantro, and salt and pepper to taste in a medium bowl. Chill until ready to use.
Grill the steak: Over medium high heat, grill steak 4-5 minutes on each side until meat reaches your desired degree of doneness.
Let steak rest 5 minutes, then thinly slice against the grain. Serve steak warm with charred corn salsa on top. Enjoy!