Preheat oven to 400°F. Place the diced squash on a baking sheet lined with aluminum foil. Toss olive oil, salt and pepper until coated. Roast for 45 minutes or until tender. Remove and allow to cool for about 10 minutes.
Transfer the squash to a food processor and add the goat cheese, parmesan cheese, egg and nutmeg. Puree until smooth. Add in breadcrumbs to make filling thicker. You'll also want to taste and season with more salt and pepper if needed.
Now heavily flour your pasta mold, otherwise it will stick when done! Lay one sheet of pasta on the mold and either use an egg to make a well or the plastic piece that comes with the mold to make the wells. Take 1 tablespoon of the filling and place it in each well.
Use your fingers or a brush to dab some water along all of the edges of the ravioli. Lay a second sheet on top and run over with a rolling pin to seal. Turn mold over to release the ravioli. More than likely they won't be fully separated so use a pizza cutter to cut the rest. Line the ravioli on a parchment lined baking sheet and cover with a damp towel. Repeat until all the ravioli is prepared. (You can freeze ravioli at this point. I usually freeze about half as there are only 2 of us)
Heat large skillet over medium heat and add olive oil. Add breadcrumbs, sage, salt and pepper and cook for about 4-5 minutes or until golden. Remove and set aside in a bowl.
In same skillet, place the butter and prosciutto in skillet and cook over medium heat until butter is browning and prosciutto is crisp. With 30 seconds left add sage leaves to get them crispy but not overdone.
Bring large pot of salted water to boil for ravioli. Boil the ravioli for about 1-2 minutes or until the float. Remove ravioli and stir in the butter sauce. Serve in plates and top with breadcrumb mixture and figs.