Make a new solid in whatever color you want your shadow to be, double click the elliptical mask tool to create a new circular mask on it, feather it out (make to look shadowy, if that’s a word 😉 ), make this layer 3D, and orient it underneath your product layer to your liking.
Then, link the Y position of the product to the scale (and maybe even the opacity) of the shadow layer using the linear() (or ease()) function something like this:
productPos = pickwhip to your product layer's y-position;
bottom = y value of product at rest on the 'floor';
top = y value of product as high as you want to make it;
shadowSmall = whatever size the makes the shadow look correct when the product is at rest;
shadowLarge = whatever size makes it look correct when the product is in the air. Eyeball it;
linear(productPos, bottom, top, shadowSmall, shadowLarge);
Apply the same concept to opacity. Dig it?