Line a rimmed baking dish with paper and preheat the over to 180°C.
Prepare pumpkin and spread onto the tray. Wrap the head of garlic in foil and add to the tray. Drizzle all generously with EVOO and season with salt and pepper.
Roast 25-30 minutes until pumpkin is tender and garlic is fragrant. Allow it all to cool. (You could do this part up to 1 day ahead of serving the salad.)
Meanwhile toast the pepitas in just a drizzle of EVOO on a medium high heat until golden and fragrant. Whilst still warm, give them a salting to taste.
To make the vinaigrette, squeeze the roasted garlic out of itself and into the TM bowl. Add lemon juice, maple syrup, mustard, eschalot and seasoning. Blend 10 se/speed 8. Add EVOO through hole in lid and combine 10 sec/speed 5.
Remove most of the dressing from the TM bowl and set aside. Fill the TM bowl to the 3/4 mark with the washed kale leaves. Add a dash more dressing on top. Chop 3 sec/speed 5. Place onto serving platter. Repeat with all remaining kale until finished, adding just about 1 tbsp dressing to each batch. FYI, the more liquid you have in the bowl when chopping, the faster the kale will chop. Also do not overfill the bowl as this will prevent you from getting an even chop.
Add roasted pumpkin, pepitas, and pomegranate seeds. Dust the whole thing like crazy with parmesan. If you do not own a microplane, you can always mill the parmesan (about 30g is heaps) in your clean dry TM bowl 10 sec/speed 9. Alternatively you could shave parmesan on top of the salad.
Drizzle the entire thing with remaining dressing and serve within a day. Kale benefits from having the dressing on it for a couple of hours. It becomes much easier to eat and digest.