Prepare the marinade: In a bowl, combine olive oil, vinegar, salt, cumin, and oregano. Toss squid tentacles to coat. Let marinate 10–15 minutes.
Roast the squid: Preheat oven to 400°F (200°C). Place squid on a baking sheet. Roast for 20–25 minutes, basting halfway through.
Prepare the sides: While the squid roasts, arrange fresh figs, olives, arugula, and goat cheese on serving plates.
Serve: Place roasted squid on the plate, then pour the pan juices over the tentacles for extra flavor. Top with fresh chopped parsley. Add the figs, olives, arugula, and goat cheese alongside.