The MIT Technology Review has a fascinating story on Obama's very tech-savvy campaign:
Of course, many of the 2008 candidates had websites, click-to-donate tools, and social-networking features--even John McCain, who does not personally use e-mail. But the Obama team put such technologies at the center of its campaign--among other things, recruiting 24-year-old Chris Hughes, cofounder of Facebook, to help develop them. And it managed those tools well. Supporters had considerable discretion to use MyBO to organize on their own; the campaign did not micromanage but struck a balance between top-down control and anarchy. In short, Obama, the former Chicago community organizer, created the ultimate online political machine.
By July 2008, the campaign had raised more than $200 million from more than a million online donors (Obama had raised $340 million from all sources by the end of June), and MyBO had logged more than a million user accounts and facilitated 75,000 local events [...]
[...] "On every metric, this campaign has operated on a scale that has exceeded what has been done before. We facilitate actions of every sort: sending e-mails out to millions and millions of people, organizing tens of thousands of events." The key, he says, is tightly integrating online activity with tasks people can perform in the real world. "Yes, there are blogs and Listservs," Franklin-Hodge says. "But the point of the campaign is to get someone to donate money, make calls, write letters, organize a house party. The core of the software is having those links to taking action--to doing something."