Thoroughly rinse produce and pat dry. Peel and halve shallot. Slice halves into thin strips (julienne). Mince garlic. Stem kale and coarsely chop leaves. Halve squash lengthwise and cut into ¼” half-moons. Stem basil, stack leaves, roll into a long cylinder, and slice across the length to create very thin strips (chiffonade).
Start the Sauce
Heat a medium non-stick pan over medium heat. Add 1 tsp olive oil and garlic. Cook 1 minute, add red cooking wine, and cook for an additional minute. Add crushed tomato, sugar, and a pinch of salt and pepper. Cook for 2 minutes.
Warm the Beef
Combine roast beef with sauce, cover, and cook for 3 minutes. Transfer to plate, cover with foil, and set aside. Wipe pan clean. Just heat the beef to warm through (165 degrees) since it's already cooked. Overcooking will make the meat tough.
Sauté the Vegetables
In a medium non-stick pan, heat 1 tsp. olive oil over medium heat. Add shallots and cook until fragrant, about 1 minute. Add kale and cook for 3 minutes. Add squash and cook 2 minutes. Season to taste with salt and pepper. Staggering the cooking of vegetables makes sure they all end up perfectly cooked at the same time.
Assemble the Sandwich
Arrange roast beef on bottom half of a Italian roll. Place sliced fresh mozzarella on top of beef. Add basil over cheese and cover with top half of roll.
Plate the Dish
Place a serving of sautéed vegetables in a serving dish and serve alongside assembled sandwich.