How Obama's Tech Team Helped Win the Election

Yet Reed has friends, such as the manager of the hip-hop club Empire who, when we walk into the place early on the Friday after the election, says, "Let me grab you a shot." Surprisingly, Harper Reed is a chilled vodka kind of guy. Unsurprisingly, Harper Reed read Steven Levy's Hackers as a kid. Surprisingly, the manager, who is tall and handsome with rock 'n'-roll hair flowing from beneath a red beanie, returns to show Harper photographs of his kids. They've known each other for a long while. They are really growing up.

As the night rolls on, and the club starts to fill up, another friend approached us: DJ Hiroki, who was spinning that night. Harper Reed knows the DJ. Of course. And Hiroki grabs us another shot. (At this point I'm thinking, "By the end of the night, either I pass out or Reed tells me something good.") Hiroki's been DJing at Empire for years, since Harper Reed was the crazy guy you can see on his public Facebook photos. In one shot from 2006, a skinny Reed sits in a bathtub with a beer in his hand, two thick band tattoos running across his chest and shoulders. He is not wearing any clothes. The caption reads, "Stop staring, it's not there i swear!" What makes Harper Reed different isn't just that the photo exists, but that he kept it public during the election.

Yet if you've spent a lot of time around tech people, around Burning Man devotees, around startups, around San Francisco, around BBSs, around Reddit, Harper Reed probably makes sense to you. He's a cool hacker. He gets profiled by Mother Jones even though he couldn't talk with Tim Murphy, their reporter. He supports open source. He likes Japan. He says fuck a lot.  He goes to hipster bars that serve vegan Mexican food, and where a quarter of the staff and clientele have mustaches.

He may be like you, but he also juggles better than you, and is wilder than you, more fun than you, cooler than you. He's what a king of the nerds really looks like. Sure, he might grow a beard and put on a little potbelly, but he wouldn't tuck in his T-shirt. He is not that kind of nerd. Instead, he's got plugs in his ears and a shock of gloriously product-mussed hair and hipster glasses and he doesn't own a long-sleeve dress shirt, in case you were wondering.

"Harper is an easy guy to underestimate because he looks funny. That might be part of his brand," said Chris Sacca, a well-known Silicon Valley venture capitalist and major Obama bundler who brought a team of more than a dozen technologists out for an Obama campaign hack day.

Reed, for his part, has the kind of self-awareness that faces outward. His self-announced flaws bristle like quills. "I always look like a f------ idiot," Reed told me. "And if you look like an a------, you have to be really good."

It was a lesson he learned early out in Greeley, Colo., where he grew up. "I had this experience where my dad hired someone to help him out because his network was messed up and he wanted me to watch. And this was at a very unfortunate time in my life where I was wearing very baggy pants and I had a Marilyn Manson shirt on and I looked like an a------. And my father took me aside and was like, 'Why do you look like an a------?' And I was like, 'I don't know. I don't have an answer.' But I realized I was just as good as the guys fixing it," Reed recalled. "And they didn't look like me and I didn't look like them. And if I'm going to do this, and look like an idiot, I have to step up. Like if we're all at zero, I have to be at 10 because I have this stupid mustache."

And, in fact, he may actually be at 10. Sacca said that with technical people, it's one thing to look at their resumes and another to see how they are viewed among their peers. "And it was amazing how many incredibly well regarded hackers that I follow on Twitter rejoiced and celebrated [when Reed was hired]," Sacca said. "Lots of guys who know how to spit out code, they really bought that."

By the time Sacca brought his Silicon Valley contingent out to Chicago, he called the technical team "top notch." After all, we're talking about a group of people who had Eric Schmidt sitting in with them on Election Day. You had to be good. The tech world was watching.

Terry Howerton, the head of the Illinois Technology Association and a frank observer of Chicago's tech scene, had only glowing things to say about Reed. "Harper Reed? I think he's wicked smart," Howerton said. "He knows how to pull people together. I think that was probably what attracted the rest of the people there. Harper is responsible for a huge percentage of the people who went over there."

Reed's own team found their coworkers particularly impressive. One testament to that is several startups might spin out of the connections people made at the OFA headquarters, such as Optimizely, a tool for website A/B testing, which spun out of Obama's 2008 bid. (Sacca's actually an investor in that one, too.)

"A CTO role is a weird thing," said Carol Davidsen, who left Microsoft to become the product manager for Narwhal. "The primary responsibility is getting good engineers. And there really was no one else like him that could have assembled these people that quickly and get them to take a pay cut and move to Chicago."

And yet, the very things that make Reed an interesting and beloved person are the same things that make him an unlikely pick to become the chief technology officer of the reelection campaign of the president of the United States. Political people wear khakis. They only own long-sleeve dress shirts. Their old photos on Facebook show them canvassing for local politicians and winning cross-country meets.

I asked Michael Slaby, Obama's 2008 chief technology officer and the guy who hired Harper Reed this time around, if it wasn't risky to hire this wild guy into a presidential campaign. "It's funny to hear you call it risky, it seems obvious to me," Slaby said. "It seems crazy to hire someone like me as CTO when you could have someone like Harper as CTO."

The Nerds Are Inside the Building

The strange truth is that campaigns have long been low-technologist, if not low-technology, affairs. Think of them as a weird kind of niche start-up and you can see why. You have very little time, maybe a year, really. You can't afford to pay very much. The job security, by design, is nonexistent. And even though you need to build a massive "customer" base and develop the infrastructure to get money and votes from them, no one gets to exit and make a bunch of money. So, campaign tech has been dominated by people who care about the politics of the thing, not the technology of the thing. The websites might have looked like solid consumer Web applications, but they were not under the hood.

For all the hoopla surrounding the digital savvy of President Obama's 2008 campaign, and as much as everyone I spoke with loved it, it was not as heavily digital or technological as it is now remembered. "Facebook was about one-tenth of the size that it is now. Twitter was a nothing burger for the campaign. It wasn't a core or even peripheral part of our strategy," said Teddy Goff, digital director of Obama for America and a veteran of both campaigns. Think about the killer tool of that campaign, my.barackobama.com; It borrowed the "my" from MySpace. 

Sure, the '08 campaign had Facebook cofounder Chris Hughes, but Hughes was the spokesman for the company, not its technical guy. The '08 campaigners, Slaby told me, had been "opportunistic users of technology" who "brute forced and bailing wired" different pieces of software together. Things worked (most of the time), but everyone, Slaby especially, knew that they needed a more stable platform for 2012.

Campaigns, however, even Howard Dean's famous 2004 Internet-enabled run at the Democratic nomination, did not hire a bunch of technologists. Though they hired a couple, like Clay Johnson, they bought technology from outside consultants. For 2012, Slaby wanted to change all that. He wanted dozens of engineers in-house, and he got them.

"The real innovation in 2012 is that we had world-class technologists inside a campaign," Slaby told me. "The traditional technology stuff inside campaigns had not been at the same level." And yet the technologists, no matter how good they were, brought a different worldview, set of personalities, and expectations.

Campaigns are not just another Fortune 500 company or top 50 website. They have their own culture and demands, strange rigors and schedules. The deadlines are hard and the pressure would be enough to press the T-shirt of even the most battle-tested start-up veteran.

To really understand what happened behind the scenes at the Obama campaign, you need to know a little bit about its organizational structure. Tech was Harper Reed's domain. "Digital" was Joe Rospars's kingdom; his team was composed of the people who sent you all those e-mails, designed some of the consumer-facing pieces of BarackObama.com, and ran the campaigns' most-excellent accounts on Facebook, Twitter, Tumblr, video, and the like. Analytics was run by Dan Wagner, and those guys were responsible for coming up with ways of finding and targeting voters they could persuade or turn out. Jeremy Bird ran Field, the on-the-ground operations of organizing voters at the community level that many consider Obama's secret sauce . The tech for the campaign was supposed to help the Field, Analytics, and Digital teams do their jobs better. Tech, in a campaign or at least this campaign or perhaps any successful campaign, has to play a supporting role. The goal was not to build a product. The goal was to reelect the president. As Reed put it, if the campaign were Moneyball, he wouldn't be Billy Beane, he'd be "Google Boy."