BEFORE GETTING TO the secret office in San Antonio or the eccentric KISS, there should be an explanation about the manner in which this journey began. Like many others, I woke up on November 9, 2016, in a state of disbelief. Donald Trump had managed to pull off the implausible — deflating the expectations of not only the public at large, but even the most seasoned political pundits around the world. Over the weeks and months that followed, I immersed myself in literature, media and dialogue that fixated almost invariably on why the result did in fact make sense. Why Trump appealed to a large segment of voters who’d grown wary of the establishment. Why sexism kept Hillary Clinton from shattering America’s ultimate glass ceiling. Why Clinton got a raw deal from the media that often ignored her positions on serious policy issues and allowed Trump to frame the coverage. Yet amidst the many well-informed arguments that I encountered, what lingered was a potent sense of enigma. I wasn’t content by simply probing into why one of the most divisive figures in mainstream politics had become the leader of the free world — I needed to know how.

I should note that my intrigue was largely driven by my interest in effective and scalable digital marketing systems. Trump and his team had managed to engage and mobilize people through digital channels in a way that few others have been able. I wanted to know what they knew, and sensed that the best route to that knowledge would have to be a quest into their world. That was the plan — to study the Trump campaign blueprint in great depth, from a strictly objective digital marketing perspective. Minimal attention would be paid to allegations or pending investigations, and all personal opinions were to be overlooked. I was intent on learning what exactly Trump and his campaign team had done right, and felt that the best way to do so would be by embarking on this path completely free of bias.

Ironically, this was my first major roadblock: I stood with her — and vehemently oppose much of what Trump stands for.

Exposition: Laying a rigid data-driven digital foundation

MORE OR LESS EVERY STORY begins with the introduction of a number of pivotal characters that give it impetus. In this one, there are three: Jared Kushner, Brad Parscale and Alexander Nix.

Kushner, Trump’s quiet (and somewhat mysterious) 38-year-old son-in-law, is largely credited as being the man behind the curtain — pulling the strings and frequently navigating the ship through the heaviest tides of chaos. He’s no stranger to controversial turf — Kushner’s billionaire father is a former New Jersey real estate mogul, who served 14 months in a federal prison after pleading guilty to 18 felony counts of tax fraud, witness tampering and illegal campaign donations. Just as Trump’s unorthodox style allowed him to stand out from his opponents, Kushner’s lack of political experience proved to be an advantage. He approached the business of politics like many entrepreneurs would a high-tech startup. “I called some of my friends from Silicon Valley who were some of the best digital marketers in the world. And I asked them how to scale this stuff. We basically had to build a $400 million operation with 1,500 people operating in 50 states, in five months to then be taken apart. We started really from scratch,” Kushner told Steven Bertoni of Forbes in a rare interview.

Helping to lead said operation was Parscale, who’d spent the early days of his career soliciting customers shopping for web development books in stores and selling his own website creation services. In 2011, he co-founded Giles-Parscale, a design and digital marketing firm that quickly established a strong reputation. Soon thereafter, Parscale was brought into the Trump Organization to provide design and digital media strategy. In early 2015, his firm was hired to create a website for Trump’s exploratory White House bid. Less than a year later, Parscale was tapped as the campaign’s digital director — a role that would see him work with in-house campaign staff as well as employees from Facebook, Google and Twitter to reach potential voters. “I asked each one of them by email, ‘I want to know every single secret button, click, technology you have, I want to know everything you would tell Hillary’s campaign plus some and I want your people here to teach me how to use it,’” Parscale revealed to CBS. Because he “wanted people who supported Trump,” Parscale has stated that everyone assigned to the campaign was questioned on their political views (a claim that has been denied by Facebook).

With Trump poised to win the GOP nomination, political analysts began drawing parallels between his campaign and the Brexit movement. Both were built upon an aggressively nationalist agenda, both portrayed immigration as a threat to national security, both displayed hostility towards political elites and both had drawn strong support from far-right voters. Convinced by the track record of Cambridge Analytica — a London-based data-analytics firm that had successfully lobbied British voters to break from the rest of Europe — Kushner and Parscale moved to secure a partnership. Enter Nix, who served as CEO of Cambridge Analytica. Before Brexit, the firm had made a foray into US conservative politics in 2014, working successfully on 44 congressional, Senate and state-level elections during the midterm elections. More recently, Cambridge Analytica had notably led Ted Cruz to victory (over Trump) in the Iowa caucus, with Nix later explaining that the victor “had the advantage of knowing his target audience better than any of the other candidates.” The firm claims to have broken down Iowa voters into 5,000 data points and built extensive personality profiles.

Together, these three protagonists worked alongside an army of marketers, data scientists and software developers — many of them stationed in an under-the-radar office in San Antonio, Texas (Parscale’s home base). Their objective was clear: to build an efficient, intelligent and cost-effective data hub that would serve to guide every strategic decision made over the course of Trump’s campaign.

Rising Action: Prioritizing decisive audience segments

IT’S SAID THAT all men are created equal. Noble as this immortal declaration may be, what modern day brands are challenged to embrace is that not everyone should be treated the same. Bear with me as I explain. Within the digital marketing world, populations are best served when categorized into different cohorts with varying needs and interests. Segmentation — as this practice is often called — enables better understanding of the subgroups that make up a large market, such that initiatives can be strategically (and more effectively) tailored to them.

Of the more than 120 million votes cast, it’s been reported that that 107,000 votes in three states effectively decided the 2016 election. Rather than trying to appeal broadly to the whole nation, the Trump campaign leveraged the data it was collecting to identify and appeal to specific voter types in key battleground states. “We never fought for the popular vote. There was no economic reason, and there was no reason based off the system of our constitution to do so. We needed to win 270 [electoral votes], and to do so we needed to win in certain states, and we needed to target registered voters that had a low propensity to vote and a propensity to vote for Donald Trump if they come,” Parscale told NPR. From there, the campaign’s digital team continued to monitor the effectiveness of their messaging in a number of areas, so as to determine whether or not they were able to win over potential voters.

Kept in mind should be the fact that that in many of these locations, Trump’s team chose to be primarily digital instead of opening physical field offices. If and when the campaign noticed positive results in one region over another, they were able to adjust resources within a matter of hours.

Climax: Building around simple yet memorable brand messaging

KISS, a backronym for “keep it simple, stupid”, is a design principle coined by the US Navy in 1960. It states that most systems work best if they are kept simple rather than made complicated. Trump’s digital team adopted a similar philosophy as it sought to differentiate itself. On the digital marketing front, this meant employing a unique approach to ad campaigns. “Fundamentally, we were trying to do two different things,” a senior digital adviser to Clinton’s campaign confessed to the Washington Post. “It’s not that one was right and one was wrong, but they were different.” Clinton, as she’d done throughout the course of her presidential bid, ran video ads that aimed to boost turnout or make a serious case for her candidacy. Alternatively, the majority of Trump’s ads were characterized by sensational language and visuals that were (in a sense) somewhat luring. In short, Trump’s and Clinton’s ads were playing entirely separate sports (never mind the same ballgame).

The simplicity of the Trump campaign’s ad strategy is (in fact) what made it incredibly agile and effective. To elaborate, the use of static images that could be tweaked in infinite, subtle ways served as a competitive advantage. In an interview with CBS’s “60 Minutes”, Parscale explained that the Trump campaign ran thousands of versions of its ads each day — up to 175,000 iterations of an ad on one day — in which changes were made as necessary to entice as many people as possible to engage.

As election day loomed, Trump’s team had not only run more ads than Clinton’s (five for every three), but also spent more through digital channels. It should be noted though that the Republican nominee did have the benefit of paying less to reach different audience segments — it’s cheaper to run ads targeting voters in red states such as Nebraska than it is in left-learning areas like Silicon Valley.

Falling Action: Results and post mortem

AND SO TO the all important question: what exactly was the impact of the Trump campaign’s digital marketing operation? “An 11.3 percent increase in favorability for Trump… and an 8.3% increase in intent to vote for Trump” according to Nix. Whether intentional or not, Trump’s digital edge was rooted in his team’s fighting-for-survival-startup-like mentality. “Our best people were mostly the ones who volunteered for me pro bono,” Kushner has said. “People from the business world, people from non-traditional backgrounds.”


I NEVER DID FEEL COMPLETELY SATISFIED with my findings. I’ve continued to search for more answers despite a part of me knowing that many of them may never come to light. Clues live in the stories that I’ve studied and restudied, as well as in new ones that I’ll encounter in the future. There’s the Trump campaign that I learned about in extensive detail. The one of the improbable White House bid that grew into one of the most successful digital campaigns in presidential history. Then there’s the Trump campaign that (for now) lingers painfully unresolved. The one soiled in controversy…of a provocative businessman that employed an ever growing list of questionable tactics to claw his way into the Oval Office. The truth, I suspect, lies somewhere in the middle. Doesn’t it always?


  • Farai Sikipa

    Development Digital Director at Children’s Defense Fund

    At present, Farai serves as Development Digital Director at the Children’s Defense Fund in Washington, DC. Previously, he's worked in growth marketing roles at venture-backed companies focused on neuroscience and artificial intelligence, financial technology and marketing technology. Farai has also written for the Huffington Post about various technology topics. Whilst in college, he built an angel-funded digital heath company (that ultimately failed). Farai received a BA in Public Policy, with a focus on Global and Domestic Health Policy from the University of North Carolina at Chapel Hill.