There are some great behind-the-scene candids at Barack Obama's Flickr account, such as this one.
Photo by David Katz
Obama's campaign was the first presidential campaign to finally "get" the Internet and genuinely harness its wide range of user generated tools and products, but most importantly, which future candidates should take note of, it was executed in a way that never felt contrived. We've officially moved from the era of Campaigning 1.0 to, yes, I'm calling it: Campaigning 2.0.
[Thanks Annie!]
Update: Related to my point above, I came across the following while reading the fascinating Newsweek "Secrets of the 2008 Campaign" 7-part series:
To the casual visitor, the New Media department at Obama headquarters seemed at once ultrahip and painfully earnest, a touchy-feely, emo sort of place where people talk about saving their souls and use lefty academic jargon like "agency." One reporter described the sentiment toward the candidate as a sort of "Lincoln 2.0." The frat brothers over in Communications liked to joke about whether the geeks in New Media were still virgins.
When it came to what they actually did, however, the nerds of New Media were cold realists. "We never do something just because it's cool," the campaign's official blogger, Sam Graham-Felsen, told a NEWSWEEK reporter. "We're always nerdily getting something out of it." He showed off the Obama '08 iPhone application. With its deep Obama blues, correct fonts and glassy graphics, it looked like an electronic bauble for the well-heeled voter. Closer inspection revealed a sophisticated data-mining operation. Tap the top button, "call friends," and the software would take a peek at your phonebook and rearrange it in the order that the campaign was targeting states, so that friends who had, say, Colorado or Virginia area codes would appear at the top. With another tap, the Obama supporter could report back essential data for a voter canvass ("left message," "not interested," "already voted," etc.). It all went into a giant database for Election Day.
Early that summer, the campaign made the unorthodox decision to announce its vice presidential pick via text messages sent directly to supporters. It wasn't just a trick to do something flashy with technology and attract media attention. The point was to collect voters' cell-phone numbers for later contact during voter registration and get-out-the-vote efforts. Thanks to the promotion, the campaign's list of cell-phone numbers increased several-fold to more than 1 million. (Among the registrees: one Beau Biden, son of Joe.)
"I don't care about online energy and enthusiasm just for the sake of online energy and enthusiasm," said Chris Hughes, head of New Media's social networking. "It's about making money, making phone calls, embedding video or having video forwarded to friends." There was nothing starry-eyed about Hughes, who had been the Harvard roommate and later partner of Facebook founder Mark Zuckerberg and made his first millions before he was 24. His goal was to make old techniques—like call centers and getting polling information to voters—more efficient. "When computer applications really take off, they take something people have always done and just make it easier for them to do it," he said. "And maybe bigger."
During the primaries, the sight was familiar at vast Obama rallies. Before the candidate appeared, a campaign official would come onstage to urge audience members to pull out their cell phones to call or text their friends and neighbors. By the thousands, people of all ages would spread the electronic word—and dollars and votes would follow.
[...]
The power of the Obama operation could be measured: doubling the turnout at the Iowa caucuses, raising twice as much money as any other candidate in history, organizing volunteers by the millions. (In Florida alone: 65 offices, paid staff of 350, active e-mail list of 650,000, 25,000 volunteers on any weekend day.) The ultimate test would come Nov. 4. In the meantime, there were indications of a great storm brewing. At the end of August, as Hurricane Gustav threatened the coast of Texas, the Obama campaign called the Red Cross to say it would be routing donations to it via the Red Cross home page. Get your servers ready—our guys can be pretty nuts, Team Obama said. Sure, sure, whatever, the Red Cross responded. We've been through 9/11, Katrina, we can handle it. The surge of Obama dollars crashed the Red Cross Web site in less than 15 minutes.