In spring 2011, Michael Slaby made a pitch to a small group of men at the West Loop offices of Sandbox Industries, a local venture capital firm and business incubator. Slaby, a Chicagoan and the chief integration and innovation officer for President Barack Obama's campaign, was recruiting talent for the re-election effort.
But he wasn't looking for seasoned political operatives. And while the members of the group gathered at Sandbox had interests in civic affairs and social activism, most had never worked on a campaign. Rather, they were friends and professional acquaintances who came up together in Chicago tech circles, honing their software chops at local companies and collaborating on personal side projects, some for more than a decade. Slaby wanted them to deploy their skills in ways that had never been seen before in a political campaign, building technology tools to help Obama for America collect donations, organize far-flung field office workers and volunteers, and get out the vote Nov. 6.
The 2008 campaign, where Slaby served as chief technology officer, had virtually no engineering staff. For 2012, he was seeking a tech team that would operate like a startup company within the traditional hierarchy of a national campaign.
"This time around, partially because I had spent a bunch of time working in venture capital and in the private sector and realized that political technology was way behind the rest of the world in sophistication and capabilities, what I wanted was to engineer our own answers to problems we'd had for years," said Slaby, who after the 2008 campaign worked at TomorrowVentures, the investment vehicle of Google Executive Chairman Eric Schmidt.
The Obama for America tech team grew to about 40 people. Now, after a grueling 18 months or so in the campaign bunker, many of these engineers are rejoining Chicago's tech community, and the excitement about what they might do next — start new companies, join or advise existing ones — is palpable.
"The people working on the campaign have had an intense year or two developing incredible techniques that should influence the tech capability and marketing scene in Chicago for years to come," said Nick Rosa, co-founder and managing director of Sandbox. "We at Sandbox are very interested in tapping into this extraordinary group of people."
At the center of the tech team was Harper Reed, a longtime fixture on Chicago's startup scene and former chief technology officer of local T-shirt company Threadless. Slaby and Reed were introduced through a mutual contact, and the two met at The Wormhole coffee shop in the Wicker Park neighborhood. It was there that Slaby learned that Reed came with an informal team, a merry band of programmers and designers who had built newly elected Chicago Mayor Rahm Emanuel's transition website in a week. The friends had also, in different permutations through the years, overlapped at Threadless, advised startups at Sandbox and helped each other on small projects.
"We had a team of core people who could really build anything, from the back-end engineering side to front-end development," said Scott VanDenPlas, who met Reed in 2001 and used to work at Threadless.
VanDenPlas was part of the group Slaby pitched at Sandbox. He signed on as the campaign's head of DevOps, meaning he oversaw the cloud-based server infrastructure on which the rest of the software ran. The others also came aboard: Dylan Richard, who became director of engineering; Jason Kunesh, director of user experience; and Aaron Salmon, a user interface and user experience engineer. Conor Gaffney, a self-taught coder who had worked on the Emanuel transition website and mayoral campaign, was committed to a nine-month master's program in history at the University of Cambridge but joined the campaign as a developer after graduating.
"Every single person who was at the first genesis meeting ended up working on the campaign," Reed said.
Reed was recruited as chief technology officer, an offer that surprised him despite his experience.
"Threadless was amazing … but it was a T-shirt company," he said. "What would happen if we screw up the T-shirt company? Christmas is sad. That's literally the worst thing that could happen in a retail organization — you ruin a holiday, you ruin a birthday. And this is terrible; you don't want to do this. But it's nothing like causing or stopping Supreme Court justices that are going to make our country better from being elected. There's a huge difference here."
The nucleus of tech talent that Reed brought to the campaign recruited talent from around the country, mostly through existing networks — "Everyone was no more than two degrees from Harper," Salmon said. The engineers worked with two other teams, one consisting of data scientists and the other made up of digital staffers minding the campaign's websites and social media efforts.
As the team started building the technology to help the campaign's efforts on the ground, it developed a culture that mixed a startup ethos with the constraints of a sophisticated political operation. Some of the entrepreneurial vibe was aesthetic; Kunesh joked that "we're the guys with the beards and you'd see the interns showing up in their seersucker suits."
Other practices were deliberately lifted from the software developer's playbook. Derek Brooks, an engineer who temporarily relocated to Chicago from Des Moines, Iowa, said the group held "stand-ups" every morning. In the software world, these are short meetings where team members share what they accomplished the day before, what they're planning for the day ahead and what their challenges are.
"Just the rate we had to scale and the scale we had to go to was nuts," said Brooks, who met Reed at Cornell College in Mount Vernon, Iowa, where the campaign chief technology officer was his dormitory resident assistant. "We did everything in an agile fashion."
The areas that VanDenPlas and Kunesh oversaw — DevOps, user experience — are relatively commonplace at tech companies but were new to a political campaign.
Kunesh, for example, was responsible for ensuring that "anything that deals with computers looks good and works well for ordinary people." One challenge he faced was making sure that Dashboard, an online field office tool that allowed volunteers to call voters from anywhere, would work just as well for a smartphone-toting 25-year-old as for a less-tech-savvy retiree. The application also had to work elegantly on desktop computers and mobile devices. Kunesh visited field offices and ran focus groups; he also persuaded more than two dozen usability experts nationwide to give feedback on the tech team's products on a voluntary basis.
In the end, "a lot of the stuff we did for mobile for younger folks was also helpful for older folks because it did some of the same types of things — like we're going to make big buttons and simple, direct calls to action," Kunesh said.
Obsessive stress testing and developing extensive backup systems was also a crucial part of the group's work. VanDenPlas said the team experienced just 30 minutes of total unplanned outages, an amount he called "a phenomenally low amount of downtime." When superstorm Sandy was hurtling toward an Amazon data center in northern Virginia that the campaign was relying on, the engineers were able to replicate every crucial application to a West Coast facility within 24 hours.
"The expectation with technology needs to be that it's going to break," said Richard, the director of engineering. "So you need to know what breaking looks like. … At any level of failure, you have to have a fallback. And we need to know when those fallbacks fail also."
The emphasis on testing also extended to the digital team, where developers made sure that the campaign's voter-facing websites and applications worked on a variety of devices, Internet browsers and mobile operating systems. Any technology platform that accounted for more than 2 percent of traffic was supported.
"We were inspired by the creative, startup-esque atmosphere that we saw in '08, and I think that was one of the things we wanted to continue," said developer Chris Wolff. "We wanted to make these the best Web properties in politics. … One of the things I'm most proud of is, everything we did was tested to the utmost. We tested on iPads, Androids, old browsers. We tested other people's properties too."
In contrast, media accounts of the Mitt Romney campaign's flagship technology product, a mobile application dubbed Orca that would help volunteers monitor swing state voter turnout on Election Day, reported that the tool crashed repeatedly, hampered by insufficient testing and limited server bandwidth.
The esprit de corps that emerged from the Obama for America tech team was in part shaped by its Chicago pedigree, said Reed, who described the prevailing local ethos as "heads down; we're going to make this happen." Kunesh characterized his campaign colleagues as sporting a "Midwestern work ethic."
Reed said Chicago's leading tech companies employ people "who are just like, 'Here's my goal. I'm going to achieve it.' They don't think about where they're going to raise money. They don't think about where they fit into the startup ecosystem in Silicon Valley. … (They run) through the battlefield to get to (their goal). And we had to do that."
With their goal accomplished, the members of the Obama for America tech team are contemplating their next steps. VanDenPlas said he and his colleagues are fielding job offers "from just about everywhere" while spending time with family and reflecting on the campaign experience.
"We did nothing special or extraordinary or anything like that on the technology side," he said. "We just did it right. We followed standards. We made smart decisions and we invented things where we needed to do it. … And in the end, you're building a $1 billion, completely disposable startup. It's just gone in 18 months."
Growing startup communities talk of achieving a virtuous cycle in which successful companies train talented engineers and other employees who eventually leave to start their own ventures, birthing additional startups that repeat the process. In Silicon Valley, for example, companies like Google and Facebook have produced new generations of entrepreneurs. Observers of Chicago's tech scene say the Obama campaign could play such a role.
On the day after his re-election, Obama tearfully thanked Chicago-based campaign staffers; the video was widely shared online. Kunesh called the president's remarks a "life changer — you can't hear that and not be affected by it." For his part, he plans to take some time off and then perhaps start a company next year that will have a "triple bottom line" of "people, planet and profit."
"I've been used to working in a lot of different venues" such as San Francisco, New York and Seattle, Kunesh said. "The thing that (the campaign) changed for me — and you'd see this with other folks as well — is, typically, when you're from Chicago and you're in technology and you're going to one of these other places, you're going to the big show from the little show. And this is (now) a chance for us to experience tremendous growth."
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