Preheat the oven to 425 degrees F.
Combine the tomato chili oil ingredients in a mason jar or bowl and shake or whisk to thoroughly combine. Let the oil infuse as you finish the dish.
Cut the kabocha squash into quarters and remove the seeds if you haven't done it already.
Wash and drain the seeds, separating them from the stringy, sticky interior of the squash.
Toss the seeds in a bowl with a pinch of salt and pepper, if using. Spread the seeds evenly on a sheet pan and roast for 7 minutes. Remove the seeds from the oven once they are golden brown and crispy. Once the seeds are removed, adjust the oven temp to 475 degrees F.
While the seeds are roasting, peel the squash with a knife or peeler. Then, cut the squash into small 1-inch(ish) cubes. If using kabocha, you can roast it with the skin on.
Toss the squash cubes in a bowl with about 1 tsp of olive oil and a pinch of salt. Spread the squash onto a sheet pan, making sure that no pieces are overlapping and that it's not overcrowded. Roast the squash for 15-20 minutes, until golden brown and tender. If the squash isn't golden brown after 20 minutes, keep going for another 5-10 minutes and check on the squash frequently so it does not burn. If necessary, roast the squash on two sheet pans.
While the squash is roasting, combine the basil and kale in a bowl. Add a pinch of salt to season the greens and toss until fully coated.
Toss the salad in 2 tsp of the tomato chili oil and add more to taste, if needed. You will be adding a little drizzle on top as well, so make sure your greens are only lightly coated.
When the squash is done, add the roasted squash to the salad. It will slightly cook the kale when you toss it, changing the pigment of the kale to a bright green.
Put the squash salad onto a plate. Top with the roasted seeds and another drizzle of tomato chli oil. Serve immediiately. If serving with cheese or protein, add those on top before drzzling with more oil and then serve.