In my experience...

There was no Chief Pilot designation or position on Active Duty (airlift world). However, in the Air Force Reserve, there was. It was an official position, and was recognized as such on your Duty History and OER. The CP duties included Hiring, liaison to airline CPs, advocating for the pilot group, low level discipline, and morale. If I were a Reservist, and had the title on my OER, I would feel comfortable checking the box.