2005–2012

After leaving school, Wylie moved to Ottawa, where he began volunteering for "a short stint" in the parliamentary office of his Member of Parliament, Keith Martin.^[3] During his time in Martin's office, he overlapped with Martin's executive assistant Jeff Silvester, who was later commissioned by Wylie to set up AggregateIQ.^[18] The following year, he got a job as a contractor in the office of the Canadian opposition leader, Michael Ignatieff, at the age of 19.^[19] During his contract, Wylie begun developing strategies on how to capitalize data harvested through social media for political gain. The party officials did not renew Wylie's contract in 2009, and a senior insider said it was largely because his ideas were seen as "too invasive." Of Wylie, the colleague said, "Let's say he had boundary issues on data even back then. He effectively pitched an earlier version of [the Cambridge Analytica data-harvesting operation] to us back in 2009 and we said, 'No."'^[20]

In 2008, he volunteered on the presidential campaign of Barack Obama, learning about microtargeting from Obama campaign adviser Ken Strasma. There has been some dispute over whether his volunteer role was a senior or a junior-level data entry role.^[21]

In 2012, Wylie worked for the Liberal Democrats in the UK on voter targeting.^[7]

SCL Elections and Cambridge Analytica, 2013–14

In 2013, Wylie discovered some research on psychological profiling using social data funded by DARPA^[7] and used that knowledge when he began working for SCL Elections, formerly Strategic Communication Laboratories, and its offshoot for American elections (later renamed Cambridge Analytica), an international consultancy specialising in data-driven psychographic targeting in elections.^[22] Alexander Nix recruited Wylie for his small team in SCL and Wylie assembled the core of what would later become Cambridge Analytica, made up of psychologists and data scientists.^[23] His role at Cambridge Analytica was reported by the Parliament of the United Kingdom as its "director of research"^[24] and by Time as a "founder,"^[7] but a Queen's Counsel (QC) report by Julian Malins disputed those titles, documenting that his employment contract stated he was hired as a part-time "intern" on a student visa, limited to 19 hours of work a week.^[25]

Wylie's role at SCL was first revealed in May 2017 by The Observer journalist Carole Cadwalladr, who wrote that "He’s the one who brought data and micro-targeting [individualised political messages] to Cambridge Analytica".^[22] He said that traditional analytics around voter profiling used voting records and purchase histories to predict voter behavior, but that it was useless for learning if a voter was "a neurotic introvert, a religious extrovert, a fair-minded liberal or a fan of the occult,"^[26] which were among the traits Wylie and his team determined were uniquely susceptible to political messaging. Wylie found research done at Cambridge University which mapped Facebook likes to personality traits, research that was done by paying users to take a quiz and download an app that scraped private information from the profiles of the participants and their friends. Academic Dr. Aleksandr Kogan was commissioned by Wylie's team to build a similar application,^[23] which illegally scraped the personal data of 87 million people from their Facebook profiles, and the data was used to develop new forms of psychographic microtargeting.^[27] Facebook denied any knowledge of Dr. Kogan's program, citing that he had said he was "collecting information for academic purposes," and agreed that it would not be used for "commercial purposes." Dr. Kogan declined to comment on the matter, citing Non-disclosure agreements with both Facebook and Cambridge Analytica, beyond the statements that his application was "a very standard vanilla Facebook app,"^[23] that Wylie's team assured him that their usage was legal, and that he did not personally profit from the work.^[27] Cambridge Analytica has repeatedly denied obtaining or using Facebook data,^[23] and further denied they influenced the outcome of the 2016 United States presidential election.^[27]

Wylie worked for American Republican candidates affiliated with the party's "Tea Party" wing in the 2014 United States elections;^[28] and on disinformation campaigns for political parties in Nigeria, Kenya, Ghana and the Caribbean.^[23][29]

Prior to his departure, Wylie had shared his profiling tool with Robert Mercer, the billionaire who funded Cambridge Analytica and later became one of Donald Trump's mega-donors, and with Steve Bannon, who effectively ran the company from 2014 onward and later went on to become Trump's campaign manager.^[7][30] Wylie's research work included message-testing work for Steve Bannon on building a wall on the American-Mexican border.^[31] He later recounted, "My ears perked up when I [later] started hearing some of these things like 'drain the swamp' or 'build the wall' or 'the deep state' because these were all narratives that had come out from the research that we were doing," and that the wall "is not really about stopping immigrants. It's to embody separation. If you can embody that separation and you can further distance in the minds of Americans us here in America and them elsewhere, even if it is just across a river, or just across a desert, then you have won that culture war."^[32]

Wylie has said he did not realize the "potential misuse" of his research at the time, referring to it as his "real failure,"^[7] and to the work he did as, "political hackery."^[13] He said that if he had taken a job offer with Deloitte, Cambridge Analytica would not exist.^[11] He resigned in 2014.^[7]

Eunoia Technologies, 2014–17

In 2014, Wylie co-founded Eunoia Technologies^[13][33] along with former SCL/Cambridge Analytica senior staff Brent Clickard, Mark Gettleson and Tadas Jucikas.^[33] In describing his ambitions for developing Eunoia, Wylie stated "I want to build the NSA’s wet dream".^[33] Eunoia Technologies has been criticized for the similar psychographic profiling tactics used by Cambridge Analytica,^[13][33] using the same dataset shared by Alexander Kogan.^{[13][33][34][35]}

In December 2014, Wylie registered Eunoia Technologies Inc in the tax haven of Delaware.^[28] In May 2015, a wholly owned UK subsidiary of Eunoia was registered in the UK as Eunoia Technologies Ltd.^[28] The name "Eunoia" meant "beautiful thinking" in ancient Greek,^[36] and the company offered election-related consultancy services including "psychographic microtargeting", "multi-agent system voter behaviour simulation", and "data & communications management".^[28]

Wylie's lawyer subsequently assured journalists that Eunoia had no data,^[36] but parliamentary testimony from Dr. Kogan later revealed that Eunoia had possessed Kogan's full data set of 87 million Facebook users; and that SCL/Cambridge Analytica had only ever had access to some 4% of the scraped data, "in contrast with the contract with Mr. Wylie’s entity Eunoia, where Eunoia received all of the page like data as well as dyads",^[37] and that unlike SCL/Cambridge Analytica, Wylie's company had been the only organization Kogan granted complete access to the dataset.^[38]

During the Easter of 2015, two of Wylie's Eunoia colleagues who had joined him from SCL, Tadas Jucikas and Mark Gettleson, flew to New York to meet Donald Trump's then-campaign manager on his 2016 presidential bid, Corey Lewandowski, for a meeting in a Central Park hotel. They pitched for Eunoia to work on the 2016 Trump presidential campaign, but were ultimately unsuccessful. The approach to the Trump campaign was made with Wylie's knowledge as CEO of Eunoia, and reportedly had his blessing.^[39]

In November 2015, Eunoia Technologies pitched Facebook data-mining techniques to the Liberal Party of Canada, securing a $100,000 contract in January 2016 for "a short-lived pilot project" with the Liberal Caucus Research Bureau. However, the contract was not renewed beyond the pilot.^[40][41]

From 2015, Wylie and Gettleson became embroiled in litigation with SCL, alleging that Eunoia had infringed SCL's intellectual property, had misappropriated SCL's data, had attempted to 'poach' other SCL contractors, and had attempted to 'poach' SCL's clients.^[28] Wylie elaborated on the Eunoia allegations when denying them: "They tried to sue me over their claims that I was somehow trying to steal their clients, or to somehow try to interfere with their contractual relations with other employees, or what have you."^[42] SCL later claimed that Eunoia had been "the subject of restraining undertakings to prevent the misuse of the company's intellectual property".^[43] A QC's report noted:

"On 21 May 2015, SCL discovered that Eunoia Technologies Limited had approached at least one of SCL’s existing clients in the USA, following confirmation from a US political client that they had received a proposal from Eunoia Technologies, which purported to deliver exactly the same services as SCL. Consequently, SCL’s lawyers wrote to Wylie and others at Eunoia Technologies Limited regarding suspected breaches of covenants on intellectual property, client solicitation, staff solicitation and non-competition."^[25]

Eunoia Technologies Ltd was voluntarily wound up in October 2017,^[28] with accounts running up to 31 May 2016.^[44]

2018–present

On 1 December 2018, Wylie was hired by H&M as its consulting director of research,^[45] eventually being promoted to its head of insight and emerging technologies.^[10]