Ross Detwiler was a U.S. Air Force fighter pilot and corporate chief pilot—flying a Dassault Falcon 7X before retiring. He also was as member of the NY Air Guard where he flew the C-5 Galaxy and attained the rank of brigadier general.
There are airline pilots who make far northern or even transpolar flights on a regular basis. Business aviators become familiar with the requirements for these flights, but we seldom do it often enough for it to be considered routine.