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Robert Jackson has held a variety of roles in the marketing and operations departments of several companies. From 2018 to present, they have been employed at Integra Credit, where they have served as Vice President of Marketing, Senior Director of Marketing, Marketing Director, and Marketing Manager. From 2016 to 2018, they worked at Enova International as a Marketing Associate, Senior Marketing Analyst, and Marketing Analyst. From 2013 to 2016, they were employed at Aon as a Benefits Operations Manager and Delivery Specialist. From 2010 to 2013, they worked at College Pro as a Senior Franchise Manager and Franchise Manager.

Robert Jackson attended the Quinlan School of Business at Loyola University Chicago and studied Finance and Economics.