Heat Canola Oil (1 tablespoon) in a large skillet. Cook Italian Sausage (10 ounce) without casing until no longer pink and starting to brown. Remove sausage to a paper towel lined plate.
In same skillet over medium heat, add remaining Canola Oil (1 tablespoon) and sauté White Onion (1/2 cup) onion for 3-4 minutes, add Garlic (2 clove) and continue to cook for another few minutes.
Stir in Kale (5 ounce), Chicken Broth (1 1/4 cup), Italian Seasoning (1 teaspoon), Ground Black Pepper (1/4 teaspoon), and Crushed Red Pepper Flakes (1 pinch). Allow to simmer uncovered, stirring occasionally until liquid is absorbed and kale is tender, about 15 minutes. There should be no visible liquid left. Remove to a large bowl and allow to cool to room temperature.
Preheat oven to 375 degrees F (190 degrees C).
Line a large baking sheet with parchment paper. Unroll Crescent Roll Dough (1 package) separate each triangle. On the prepared pan, place 4 triangles in a horizontal line, lining up the corners of the shorter side.
Place remaining 4 triangles parallel to the first 4, joining the bottoms of each triangle. 4 triangle tips will be pointing toward you while the other 4 away from you. Press dough together along the seam and press out slightly with your fingers, creating an approximate 3-inch dough surface for the filling.
To the kale mixture, stir in sausage meat, Gruyère Cheese (3/4 cup) and Parmesan Cheese (2 tablespoon). Scoop out filling onto prepared dough bed in a straight horizontal line, keeping filling on the dough seam and leaving a 1-inch border at the ends.
Slice Roma Tomato (1) into 1/4-inch thick slices and lay slices in a flat row along the top of the filling row. Sprinkle tomatoes with remaining Parmesan Cheese (2 tablespoon).
Lift and bring triangle tips over and across filling, alternating tips. Cut excess dough from triangle tip and tuck end under. Use any excess dough to stretch and cover any filling spots that get missed in the first pass. Tuck and pinch ends together. The roll should be approximately 14-inch long.
Whisk Large Egg (1) with a 1 Tbsp of water and brush over the roll. Bake in preheated oven for 25-30 minutes.
Remove and cut into 2-3-inch slices and serve immediately.