Grill Corn: Ensure grill grates are clean and preheat grill to 450℉. Place 3-4 ears of fresh sweet corn (after being shucked) on a plate or baking sheet. Very lightly drizzle with extra virgin olive oil and use your hands to massage oil into each ear of corn. Sprinkle lightly with kosher salt. Grill sweet corn on direct heat for a total of 10-15 minutes, turning once or twice with grill tongs. Remove when corn is slightly charred. Let cool slightly and then cut off corn kernels from cob.
Combine Dressing: In a small bowl whisk together 2 tablespoons extra virgin olive oil, 2-3 teaspoons garlic, 1 teaspoon lemon juice, ½ teaspoon Italian seasoning, ¼ teaspoon kosher salt, and ⅛ teaspoon ground black pepper.
Combine Salad: In a medium bowl combine grilled corn kernels, 2 cups cherry tomatoes, 2 cups English cucumber, and ¼ cup red onion.
Toss + Taste: Drizzle dressing over top and give it a toss. Taste and add additional salt or Italian seasoning, as desired.