OTWO has come up with inique perspective; I don't thin i've ever seen this specific point made on the forum in the past. You are right that the path to prominence in dubdom is through the Pioneer ranks. I had never made the connection you did, however, that all the upper leadership boys have pioneer backgrounds.
While I met some pioneers I respected, they were the ones who did it with no ulterior motive (or none that was obvious, at any rate). Many others were doing it to enhance their personal reputations and finding all sorts of ways to "pioneer" with the least amount of exertion. Thus the dub language is filled with expressions such as "the pioneer pace" or "pioneer spirit." The average dub knows that when you hear 'pioneer spirit" from the platform, it's presented as positive, but when you hear it in private conversation it usually refers to someone's unbalanced sense of entitlement. As for the pioneer pace, that's dub slang for padding one's field service hours.
Those who pioneer, especially for a long time, lose their sense of perspective as well as their empathy for others. They feel entitled to privilege. They don't usually hold down real jobs but work outside the box by cleaning homes or offices or washing windows; they gravitate toward service jobs which allow them to "make the most money in the least amount of time" and often look for opportunities to gouge their employers.
The strong personal sense that they are owed a living permeates their relationships with others. This is why CO's and other mucky-mucks not only accept but expect green handshakes (although this is a misnomer in my experience; it's more often an envelope with a "thank you" card enclosed, stuffed with money or a check). And, since we we are now talking money, this bit of information: In the U.S., the IRS allows anyeone to accept a gift from another person of up to $12,000 a year with no tax consequences, so none of these much smaller gifts are reportable.