(Bloomberg) -- Raffi Krikorian was asleep in a Chicago hotel room at around midnight one Wednesday in August when his phone buzzed. Krikorian, who had become chief technology officer of the Democratic National Committee about a year earlier, was in town for the committee’s summer meeting. He was feeling sick, so when his colleagues headed to the bar he turned in, hoping to get some rest. The call was from Bob Lord, whom Krikorian had recently hired to lead security for the DNC. As Lord talked, Krikorian realized he’d have to scrap his plans for a restful evening.

According to Lord, someone had set up a fake version of Votebuilder, a tool run by the Democratic data firm NGP VAN, using gift cards to pay for the servers in order to cloak their identity. It looked like the first step of a ploy to dupe staffers into sharing their passwords. A similar attack in 2016 had let to the release of embarrassing internal documents, and—by some accounts—had tipped the presidential election in favor of Donald Trump.

Such a breach was arguably the worst thing that could happen to Krikorian. He was the Silicon Valley guy the Democrats were counting on to fix their creaky technology; before joining the party, he had held senior positions at Twitter Inc. and Uber Inc. For much of the night and the following day, Krikorian was glued to the phone, and by the next afternoon, he was confident that the episode was a validation, not a disaster. The DNC had detected the attack, and no accounts had been compromised.

On Thursday, DNC officials told reporters that the party had thwarted an attempted hack, and the FBI was on the case. Then some sheepish volunteers from DigiDems, a group that recruits and trains digital organizers to work on Democratic campaigns, contacted the DNC. They’d set up the phony site as a security test, as part of the group’s work with the state party in Michigan.

That it hadn’t occurred to anyone to tell Krikorian’s staff beforehand highlighted a particular challenge of his position. People regularly talk about the Democratic party as though it is a single organization, the team that faces off against the Republicans. In fact, it’s a constellation of campaigns, local parties, national committees, and private companies, all pulling in (more or less) the same direction. Krikorian's power over—or even visibility into—much of the broader Democratic world remains limited. “We’re trying to work in a decentralized way,” he said. "This wouldn’t have happened at a technology company.”

The Democratic party knows it has fallen far behind the GOP in tech savvy. Creative digital strategy was a signature attribute of Trump’s campaign, made possible in part by a years-long effort by the Republican Party to build data infrastructure. Democratic digital operatives bemoan as unethical efforts led by Brad Parscale, Trump’s digital director, to drive down turnout among black voters, as well as the Trump-affiliated firm Cambridge Analytica’s use of Facebook data it obtained through questionable means. They also acknowledge Parscale’s operation as a clever, if relatively basic, example of how to do targeted political advertising. Trump has already tapped Parscale to run his re-election effort.

Overall, Democratic candidates spend a smaller proportion of their advertising budgets than Republicans on digital ads. Their counterpart to the Republicans’ data infrastructure, a master list of information about potential supporters known as the voter file, is in dire need of an overhaul. Democrats complain that their innovations tend to disappear after Election Day, when the people who build them move on to other jobs, a phenomenon that one frustrated engineer called “electoral abandonware.”

Krikorian’s primary goal is to build a lasting data and tech foundation that Democratic candidates and organizations can use as the basis for their own innovations. Since he joined the DNC, his team has swelled to 35 people, an all-time high for the committee and about a quarter of its total staff. But the DNC hasn’t solved its chronic financial struggles—it had $10.3 million in cash at the end of September and more than $7.3 million of debt and obligations, according to financial disclosure—and is also in deep reputational debt. Many Democrats haven’t forgiven the committee for its failings during the 2016 campaign. They’re skeptical that innovation can come from the traditional machinery of the party instead of via scrappy campaigns and independent startups. For Krikorian, the rancor coming from ostensible allies has been one of the biggest shocks of his first foray into politics. “I probably didn’t do enough research about how much people would hate me,” he said.

Krikorian is a soft-spoken engineer who grew up in Queens, New York, to a Syrian father and a Filipino mother. Krikorian, now 40, said that he was always intellectually interested in politics, but described that interest in a way that makes clear why he went into engineering: “The systems problem is super-fascinating,” he said.

Krikorian studied and then taught at MIT. After school, he tried his hand as an entrepreneur, first founding a tech consultancy and then a startup that made a tool to measure personal energy consumption. He joined Twitter in 2009 and made a name for himself by eliminating the Fail Whale, a large cartoon creature that appeared whenever the service was overcome by traffic.

During the Obama years, the administration began to poach many of Krikorian’s colleagues. In turn, some of his friends tried to lure him to work in government. Krikorian and his wife, a computer science professor at Stanford, took the idea seriously but ultimately couldn’t bring themselves to move to Washington. Later, after Krikorian left Twitter to lead Uber’s self-driving-car division, another friend attempted to get him to join Hillary Clinton’s presidential campaign. Once again, he declined.

The regret kicked in as Krikorian watched the 2016 election results. “This isn’t the world I was taught about when I was younger,” he said. Krikorian called some old friends who had worked for Obama and told them he wanted to get involved. Several months later, he found himself trying to explain to DNC officials how clueless they were about technology. He also considered joining the ACLU. Last summer, the DNC hired him.

People who have worked with Krikorian describe him as a soothing, egoless presence. He found himself having to lean hard on these attributes once he started traveling as a representative of the DNC. Early in his tenure, he met with a group of programmers who had worked with Bernie Sanders. They launched into a rant about all the ways the DNC had stymied their insurgent campaign.

It was Krikorian’s first real exposure to the leftover bitterness from the 2016 campaign. This bitterness, as well as institutional resistance to jettisoning such traditional strategies as television advertising, has consistently colored Krikorian’s work. Shomik Dutta, co-founder of Higher Ground Labs, an incubator for political tech startups that has worked closely with Krikorian, credited him with pushing people within the traditional Democratic machinery to open up to the wave of new players that has emerged since Trump’s election. “The good news and the bad news is that this is a political problem,” Dutta said.

But it will be hard for the DNC to improve its positioning within the broader Democratic landscape, said a senior Democratic operative who spoke on the condition of anonymity to avoid alienating political allies. This is largely a matter of expectations. The DNC doesn’t control the party’s messaging, and is only a supporting player on the campaign trail. Broadly speaking, the committee just doesn’t have the power to do what many people assume it is supposed to be doing. “It’s a problem that the DNC is a weak organization,” this person said. “It’s an even bigger problem that people expect it to be a big organization.”

Anton Vuljaj, a former Google employee who is now a Republican digital consultant, says his party’s superiority in technology came from its forced march through wilderness during the Obama years. People in Republican politics were beset by an urgency to regain power, and donors were happy to fund ambitious projects that would help. This led the GOP to build a data operation that could serve as the foundation of a digital campaign for whatever candidate came along. Then the Republicans stumbled onto a nominee whose approach to digital campaigning was unusually experimental.

“I’m intrigued to see how the Democrats will respond to this situation. They’re in the same spot we were,” said Vuljaj. When asked for evidence that the GOP’s edge in tech may be eroding, he drew a blank. “I just don’t see much,” he said.

One of the DNC’s core functions is helping maintain the voter file. This data is cobbled together from information gathered from campaigns and state parties and purchased from private vendors.

Many political tools, from targeted advertising to last-minute SMS messages that remind people to vote, rely on accurate and detailed information about voters. While the GOP has a centralized effort to maintain its data, the work on the Democratic side fell largely to the state parties over the Obama years. This has resulted in a disjointed national database.

Improving this situation has taken up more of Krikorian’s time than any other single project. Dutta of Higher Ground Labs said Krikorian's willingness to do such groundwork is a necessary underpinning for a lot of the more visible work in digital campaigning. “It’s boring,” he said. “But without the G.W. Bridge, you can’t get into Manhattan.”

Krikorian has also pushed state party officials and campaigns toward collaborating with startups. He has arranged several meetings between state party officials and companies coming from Higher Ground Labs. The DNC has also built a website called IWillRun.org endorsing tech vendors that provide various services to campaigns.

In some instances, the DNC has piloted tech directly as a proof of concept. During the Alabama special election to replace Attorney General Jeff Sessions, the group identified about 250,000 voters that hadn’t been contacted by the campaign, according to Krikorian. The DNC sent hopeful messages to a subset of them, along the lines of: “You can make a difference by voting!” Krikorian said that those who received the messages turned out at higher numbers than those who didn’t, although a DNC spokesperson declined to provide specific information.

In Arizona, the DNC signed a small contract with Swayable, a service that uses Mechanical Turk and other crowdsourcing methods to test video advertisements to determine which messages were convincing. The product proved useful, and the DNC suggested other campaigns try it as well.

“The effect of them having tried the tech and spending significant efforts to validate our claims, that was very valuable,” said James Slezak, Swayable’s co-founder and chief executive officer. “Our main problem was that we had made something important and new, but we’re in the middle of this landscape where people are making crazy claims all the time.” The company now has about 30 clients, almost all of them Democratic political campaigns. 

Last month, Howard Dean, formerly a presidential candidate and DNC chair, participated in a public discussion about the intersection of technology and politics. The host was Jennifer Alter, co-founder of Tech for Campaigns, a group that has recruited thousands of volunteers to help Democratic candidates with digital operations. It’s the sort of work one might imagine the DNC carrying out. “We’ve all picked off sections of the pie that really, the DNC should be doing—and we do it better,” Alter said.

Dean agreed. “I fundamentally don’t think you can change the institution of the Democratic Party. I think you should ignore it,” he said. The role of the DNC, he said, shouldn’t extend far beyond organizing the party convention. “The Democratic establishment is not going to look anything like it does today 10 years from now. It’s going to become less and less important.”

In a subsequent interview, Dean told Bloomberg News that he thought Krikorian had been making the best of a challenging situation. “If Raffi could do whatever he wanted, we’d be fine,” he said. “This is an internal politics problem.”

The pushback from other Democrats has worn on Krikorian. “I want to say you let it roll off your back, but there are 35 people on my team who feel the animosity,” he said. Still, Krikorian agreed in part with Dean’s argument. Krikorian has looked to jettison the DNC’s role in some areas: No one at the DNC should ever code an app, he said, when there are plenty of good developers for hire. Krikorian has also outsourced some modeling of voter data to outside firms.

But Krikorian thinks that there are certain things that it makes sense to do only through a centralized institution such as the DNC. He worries that today's political startups are more vulnerable to the extreme highs and lows of the electoral cycle than they'd like to admit. This is something that's likely to become clear only after the next presidential election, when money and energy for campaigning tend to dissipate. “There’s been no evidence from outside organizations that they’ll be able to withstand the boom-and-bust cycle. They all show up, and then disappear, and the DNC is the only one left standing,” he said. “Knock on wood, we win in 2020. But win or not, I want the team in 2021 to be building on top of us, instead of starting from scratch.”

To contact the author of this story: Joshua Brustein in New York at jbrustein@bloomberg.net

To contact the editor responsible for this story: Emily Biuso at ebiuso@bloomberg.net

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