McKay's career started in college when he became Vice President of Student Affairs at the New College Student Alliance. During that time he acted as a representative to the Florida State Students Association (FSSA) and managed the New College student body President’s campaign for an FSSA leadership position. His next gig was as Maintenance Foreman for the New College of Florida where he supervised all operations of a 26 person staff. 
McKay spent the next nine months as a Finance Data Director at the Clyde Williams for Congress campaign where he helped raise over $418,000 and designed all campaign materials from scratch. McKay then had a short stint as a Campaign Outreach Consultant for the Hoboken Mayor's Office. 
McKay then got his break in the world of journalism, becoming a Staff Writer at Mic. As Staff Writer, McKay helped hone Mic's editorial voice, generating millions of unique page views from coverage of breaking stories. During the four years McKay worked at Mic their unique visitors climbed from under five million to tens of millions (though as of 2019 Mic's engagement is well below five million unique visitors).