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James Reagan began their professional career in 2011 as a Team Leader for Gatorade Summer Camps. In 2013, they held two internships simultaneously, one as a Marketing Intern for the University of Notre Dame Development Department, and one as a Marketing Intern/ Student Ambassador for Doctor's Express. James then worked as a Digital Marketing Strategist for Vennli in 2014. From 2015 to 2017, they worked at Brad's Deals, starting as a Digital Marketing Coordinator and progressing to a Digital Marketing Specialist. Finally, they moved to SpotHero in 2017, where they worked as a Marketing Analyst, Senior Marketing Analyst, and Marketing Analytics Manager. During their time at Brad's Deals, they co-managed and optimized acquisition channels, resulting in a decrease in CPA and a record-breaking lead volume. James also wrote SQL queries and manipulated data in Excel to create actionable reports.

James Reagan attended the University of Notre Dame from 2011 to 2015, where they earned a Bachelor of Business Administration (B.B.A.) in Marketing.