1. Heat a skillet over medium heat and add 1 tablespoon of olive oil.
2. Add shrimp to the skillet and cook until pink and opaque, about 3-4 minutes per side. Remove from heat and set aside.
3. In a large mixing bowl, combine cherry tomatoes, cucumber, red onion, Kalamata olives, and feta cheese.
4. In a small bowl, whisk together the remaining olive oil, lemon juice, dried oregano, minced garlic, salt, and pepper.
5. Pour the dressing over the salad and toss to combine.
6. Add the cooked shrimp to the salad and gently toss to combine.
7. Serve immediately or chill in the refrigerator for up to 2 hours before serving.