Last week, as the Republican National Convention kicked off, we took a look at how the party has attempted to rejuvenate its digital strategy following the disastrous 2012 election. While establishment Republicans may have embraced the power of data-led campaigns targeting swing voters, Donald Trump’s bid to become the Republican nominee broke all the rules, including the ones that had only just been made. Trump has vocally rejected the impact that data analytics can have on political campaigns, focusing instead on the power of his social media presence and ability to electrify a significant mass of Republican voters.

While Republican political consultants and campaign workers struggle to bridge the gap between the party’s nascent digital ambitions and Trump’s reliance on his outlandish social media persona, Democrats are facing a different challenge. Following the successes of Obama’s 2012 digital strategy, the Hillary Clinton campaign is asking how it can build and evolve on the most sophisticated digital election in history.

As voters gather in Philadelphia, Pennsylvania for the Democratic National Convention, we take a closer look behind-the-scenes at Clinton’s digital operation and ask if she can compete with Trump’s headline-grabbing antics on social media.

Rise of the Machine
When describing political campaigns, it’s common to trot out a number of mechanical clichés – running like a well-oiled machine, politicians who grease the wheels, etc – but if the traditional campaign is a machine, it’s a locomotive, often running on tracks that have been laid by decades of conventional wisdom. The vast and complex nature of a political campaign makes it hard for those involved to pivot quickly based on new information in the same way an agile startup can, but that’s exactly the sort of tactics the Democratic National Committee has been trying to instil in its workers over the past four years, at every level from the presidential contest down to local races.

The DNC hoped to take the lessons learned from Obama’s 2012 campaign and expand on them, integrating digital and data driven campaigning throughout its political operations. The party ran political ‘wargames’, pitting operatives and politicians against each other in the race for fictional congressional seats and demonstrating how data science could help power donations, extend the reach of advertising and even build their volunteer base.

These projects weren’t just about strengthening down-the-ticket races, and teaching activists and local organisers to use HTML and operate analytics software. They were also about maintaining a digital lead over the Republicans, who had taken the 2012 defeat as a wake-up call to the power of digital. In order to keep the digital edge in a world where every advantage counts, Democrats would have to push harder to embrace new technology and new methods of campaigning.

Hillary Clinton’s campaign team has had a considerable overhaul since her first attempt at the Democratic nomination in 2008, when she was on the receiving end of Obama’s technical proficiency which activated young voters to donate and volunteer in unprecedented numbers. She has brought in a younger, more technically proficient staff headed by Katie Dowd, who previously served as a senior adviser to the White House’s chief technology officer, and worked on tech projects at the State Department.

“We have to think about where the audiences are,” said Down in an interview with Fortune magazine; technologies like mobile live-streaming app Periscope will fundamentally change how campaigns operate and the focus will be on “letting people feel like they are part of the real-time movement of the campaign.”

The campaign has moved beyond email and is using everything from Twitter to Snapchat and Pinterest to reach out to voters, and in turn draw in as much information as possible on what messages draw the most engagement, and from whom. However, despite the expertise that Hillary and her team have shown in embracing the power of data and digital marketing methods, there has been a barrier to her success that no amount of analytics training can help with – the authenticity problem.

Inside Game
Despite his status as a billionaire who benefitted from inherited wealth, Donald Trump has managed to run a hugely successful campaign that has positioned him as an outsider in the political sphere, someone who will come in and disrupt business-as-usual in Washington and stand up for people who feel they have been left behind by traditional politicians.

Many elements of Trump’s campaign have been tailored to support this message, such as his refusal to accept corporate donations for his primary campaign, instead largely self-funding his journey to becoming the Republican nominee. However, one of the most important has been the tone of his social media presence, which has maintained an authentic voice throughout while attacking “Crooked Hillary” as the latest in a series of political dynasties, and removed from the needs of everyday Americans.

Hillary’s social media messaging his struggled to react to these attacks, and is still fighting back against the perception that her campaign and candidacy is a slick operation lacking heart. Trump’s social media presence may be controversial and polarising, but one cannot doubt that he is steering the ship, if for no other reason than his creative approach to grammar. Meanwhile, Hillary’s online presence has been criticised as feeling too managed and staged, which has only fed into negative public perceptions.

There are signs that Hillary’s social team are beginning to turn this around however, using pop culture and modern idioms to respond to Trump’s attacks. When Donald Trump attacked President Obama for his endorsement of Clinton, she fired back within five minutes with “Delete your account”, a response that went on to become her most popular tweet ever, with over 600,000 likes and close to half a million retweets.

The shift from the relatively composed tone of the Democratic primary battle to the Presidential campaign against Trump has enabled Clinton’s team to be more direct and combative on social media, attacking his outlandish claims and lack of coherent policies. A recent campaign by Priorities USA, a Super PAC supporting Clinton, ran ads on Facebook, Instagram and Pandora, targeting voters in nine key swing states with video ads that showed some of Trump’s controversial comments on women, immigration and the environment, followed with a cartoonish “WTF?”.

Messaging from a Presidential campaign that deploys teenage slang may not feel like high-minded debate, but the rise of an outsider like Donald Trump marks the 2016 election as one that doesn’t play by many of the conventional rules of politics-as-usual. That may make the preparations that the DNC made, as it tried to embrace Silicon Valley-style digital agility, all the more important in the months ahead as both sides attempt to outmanoeuvre and undermine the other, leveraging every possible advantage in what is sure to be a bloody and cut-throat fight for the Presidency.