There are different ways to do this, but in my world, I'd use 14/2 from the power to the first switch, then 14/4 between the two switches (two travellers, a neutral being passed along, and a "traveller" for the pilot light), and 14/2 from the second switch to the light fixture. If only the second switch needs to include a pilot, then you can eliminate the pilot light wire, and use 14/3 cable.

Thanks for your response... it covered something I hadn't thought of.

As the boxes stand now, the light that needs the pilot is the "first" box, which means I need the additional traveller.

However, the boxes are so close (back-to-back) that I can move the 14-2 that currently goes to the light into the box that need the pilot effectively switching the "first" and "second" boxes, eliminating the additional traveller between boxes and simply use a pigtail connected to the pilot and the load.

Thanks!