I have to say that I have been very impressed the level of planning at the Obama campaign. Their ability to design, deploy, and operate the messaging and organization structure with this level of visual, message and content sophistication - is great. (I mean, they even have sophisticated typography.)
Who is the systems thinker over there? If it's Obama himself we could add another first to this election season (first real planner in the oval office.)
Not sure who the chief planner for the campaign. But I know that when it comes to the social networking on the Internet, which is an important part of the success, Chris Hughes left Facebook a while ago (one of the founders) to help Obama.