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FOR THE ROASTED SQUASH: Adjust oven rack to middle position and heat oven to 425 degrees. Toss all ingredients together in bowl. Spread vegetables in single layer on rimmed baking sheet. Roast until squash and onion are browned and tender, 35 to 45 minutes, stirring halfway through roasting. Remove sheet from oven and let cool for 15 minutes.
FOR THE DRESSING AND SALAD: Meanwhile, whisk tahini, water, mayonnaise, lemon juice, garlic, salt, and pepper in now-empty bowl until creamy and thoroughly combined, about 30 seconds.
Reserve ¼ cup dressing. Add arugula to remaining dressing in bowl and toss to combine. Season with salt and pepper to taste. Spread arugula on large serving platter. Top with squash and onion, pecans, olives, and mint. Drizzle salad with reserved dressing. Serve.
TO MAKE AHEAD: Cooled cooked vegetables can be refrigerated for up to 24 hours. Let sit at room temperature for 1 hour before assembling salad and serving. Dressing can be refrigerated for up to 3 days but may thicken over time. If dressing becomes too thick, adjust consistency with water as needed.