Grill Corn: Ensure grill grates are clean and preheat grill to 450 degrees F. Place clean, shucked ears of sweet corn on a plate or baking sheet. Very lightly drizzle with olive oil and use your hands to massage oil into each ear of corn. Sprinkle lightly with 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 olive oil, garlic, lemon juice, Italian seasoning, kosher salt, and ground black pepper.
Combine Salad: In a medium bowl combine grilled corn kernels, cherry tomatoes, red onion, and cucumber.
Toss + Taste: Drizzle dressing over top and give it a toss. Taste and add additional salt or Italian seasoning, as desired.