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Caroline Riley has a long history of work experience in customer service. Caroline began their career in 2006 as the Customer Service Manager at Overton's, where they managed customer service, sales, and technical sales teams and was responsible for 375,000 calls annually. In 2011, they moved on to become the Call Center Director at Gander Mountain, where they handled 850,000 calls annually and oversaw the migration to a new customer service system and time management system. From 2013 to 2019, Caroline was the Director of the Patient Advocacy Team at Airrosti Rehab Centers, where they set up a new operations center from scratch, created the organizational layout, and established efficient and quality-oriented operations. Currently, Caroline is the Head of Customer Experience at Ownwell, a position they have held since 2022.

Caroline Riley has studied Communications at both Ball State University and the University of Southern Indiana.