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NY Times, Feb. 5, 2020
Faulty Iowa App Was Part of Push to Restore Democrats’ Digital Edge
By Matthew Rosenberg, Nick Corasaniti, Sheera Frenkel and Nicole

The faulty smartphone app behind the chaotic aftermath of Iowa’s Democratic caucuses was the work of a little-known company called Shadow Inc. that was founded by veterans of Hillary Clinton’s unsuccessful presidential campaign, and whose previous work was marked by a string of failures, including a near bankruptcy.

The app grew out of a broader push by Democrats, backed by tens of millions of dollars in donor money, to match the Republicans’ prowess in digital advertising and organizing after the 2016 election. Much of the energy and investment have gone into enterprises that are intended to both boost the Democrats’ digital game and turn a profit, like Shadow.

Yet instead of showcasing how far the Democrats had come since the 2016 defeat, the disarray surrounding the Iowa caucuses raised new questions about how the party hopes to compete in 2020 with the Trump campaign, a digital juggernaut that is churning out ads and raising record sums of money.

“It’s the exact opposite of the Trump team approach — bring the engineers in house, figure out exactly what we need, we build it, we test it, we own it,” said David Goldstein, chief executive of Tovo Labs, a progressive digital consulting firm.

Given less than two months to build an app for reporting caucus results to the Iowa Democratic Party, Shadow produced technology that proved difficult to download and use and ended up delivering incorrect tallies. Iowa’s Democrats blamed a “coding issue” in the app, and the party said it would resort to a time-consuming manual tally based on information called in by precinct chairs or pictures sent on their smartphones — the same ones on which they could not make the app work.

With the wait on results dragging into Tuesday evening, many in the party began dissecting what turned the Democrats’ first contest of the 2020 election into a chaotic display, starting with Shadow, and its main backer, Acronym, a progressive nonprofit that is focused on helping Democrats regain their digital edge.

Shadow, in a tweet, said, “We sincerely regret the delay in the reporting of the results of last night’s Iowa caucuses and the uncertainty it has caused.” But the company offered no explanation for what went wrong, though Democratic officials said that data had been incorrectly transmitted from the app to a central database, and that many users had been unable to follow the complicated process for installing the app on their phones.

The fallout spread quickly on Tuesday. Nevada, which like Iowa holds caucuses instead of a primary election, said it was abandoning plans to use Shadow’s app. The Biden campaign, which had hired Shadow to help it reach voters, announced that it had cut ties with the company last year.

Founded in 2017, Acronym quickly became a darling of the Democratic donor class with its talk of restoring the digital advantage that the party had enjoyed under President Barack Obama, and that it was seen to have lost in Mrs. Clinton’s 2016 campaign. David Plouffe, the well-connected former Obama campaign manager, joined Acronym’s board. Its founder, Tara McGowan, a former journalist, was the subject of glowing profiles, one of which called her “the Democrats’ Most Dangerous Digital Strategist.”

For a time, Acronym appeared poised to deliver on its promise. Late last year, it unveiled a plan to spend $75 million on digital advertising to counter President Trump’s early spending advantage in key battleground states.

Months earlier, it also quietly invested millions of dollars in a nearly bankrupt company called Groundbase, a tech firm that renamed itself Shadow soon after.

The firm had been founded by a pair of Clinton campaign veterans, Gerard Niemira and Krista Davis, with an initial investment from another progressive nonprofit, Higher Ground Labs. But its main technology, a texting platform designed for campaigns, failed to catch on as users complained that it was slow and cumbersome.

The failure left the firm perilously underfunded, and it was close to shutting down when Acronym stepped in with an infusion of cash, and a plan to refocus Groundbase specifically on developing mobile technology for campaigns.

The new money brought new projects. There was an email app and a program called Lightrail, which was being built to help the Democratic Party centralize its data.

There were also new clients. According to the most recent campaign filing reports, Shadow earned roughly $150,000 last year working for the Nevada and Wisconsin state Democratic parties and three presidential campaigns — those of former Vice President Joseph R. Biden Jr., Pete Buttigieg, former mayor of South Bend, Ind., and Senator Kirsten Gillibrand of New York, who dropped out of the race in August.

Shadow’s work for the Biden campaign involved the texting technology and digital advertising consulting aimed at small dollar donors, said campaign staffers. But the texting program was particularly problematic, they said, pointing to potential security concerns.

An aide to Mr. Biden, who spoke on the condition of anonymity to avoid alienating other Democrats, said the campaign had used Shadow to text voters ahead of its campaign kickoff in Philadelphia last year. But the technology “did not pass our cybersecurity checklist.”

Still, when Iowa Democrats, on the advice of the national party, abandoned plans to have caucus results called in by phone because of security concerns and instead build an app, they chose Shadow from multiple bidders, according to a state party official. The party said that Shadow’s application was vetted for cybersecurity and technical considerations, including by third-party experts.

State records show the Iowa Democrats paid the firm $63,183 in two installments.

Shadow was put into a race that engineers at the most well-resourced tech giants, like Google, said could not be won. There was simply not enough time to build the app, test it widely to work out major bugs and then train its users.

Shadow was also handicapped by its own lack of coding know-how, according to people familiar with the company. Few of its employees had worked on major tech projects, and many of its engineers were relatively inexperienced.

Two people who work for Acronym, speaking on the condition of anonymity because they did not want to risk their jobs, acknowledged that the app had problems. It was so rushed, they said, that there was no time to get it approved by the Apple store. Had it been, it might have proved far easier for users to install.

Instead, the app had to be downloaded by bypassing a phone’s security settings, a complicated process for anyone unfamiliar with the intricacies of mobile operating systems, and especially hard for many of the older, less tech-savvy caucus chairs in Iowa.

The app also had to be installed using two-factor authentication and PIN passcodes. The information was included on worksheets given to volunteers at the Iowa precincts tallying the votes, but it added another layer of complication that appeared to hinder people.

In the end, only one-quarter of the 1,700 precinct chairs successfully downloaded and installed the app, according to a Democratic consultant who spoke on the condition of anonymity to avoid losing work. Many who resorted to calling in the results found that there were too few operators to handle the calls.

Some also took pictures of the worksheets they had been given — the PINs fully visible — and tweeted them out in frustration. Had the app worked, the information might have given trolls or hackers a chance to download the program and tamper with it.

In the lead-up to the caucuses, officials at the state party and the D.N.C. made an effort to keep Shadow’s involvement a secret, asking with no apparent irony that even the name of the company be withheld from the public, arguing that hackers could not attack what they did not know existed. But the relative obscurity meant that the app would not be subject to independent testing for bugs.

By Tuesday morning, it appeared that some of the people involved with developing and launching the app were trying to hide their connection to Shadow. At least one employee had removed the company from her LinkedIn profile, and two others had hidden their photos and personal details online.

Acronym, for its part, removed a mention of its role in developing the app from its website. In its place, the Acronym website now states that the organization “invested” in Shadow.

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