The Iran map is pretty obviously a bitmap image that has been traced by Inkscape's "trace bitmap" extension. It's not perfect, but it works (especially for smaller images - personally I'm not a fan of the Iran background).
Roads of Silk and Iron looks like it's just hand drawn, directly in Inkscape (or AI, not sure which Ollie uses).
Edited 7/4/2020 20:41:03
Map with image for a background: 7/4/2020 19:17:01