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Kiley Brennan has held a variety of roles since 2017. Kiley began their career as a Camp Counselor for Arbors Kids LLC in 2017. Kiley then moved on to become an IT Help Desk Consultant for Providence College in 2018. In 2020, they held a Hayley Petit Injury and Violence Prevention Fellowship at Connecticut Children's. Kiley also held internships at HopeHealth as a Quality Intern and at Teladoc Health as a Clinical Operations Intern that same year. In 2021, they worked as a Sales Associate for Orangetheory Fitness and a Health Professional Outreach Intern for the Connecticut Coalition Against Domestic Violence. Currently, they are a Customer Success Manager for Wellable.

Kiley Brennan attended Providence College from 2018 to 2022, where they earned a Bachelor's degree in Health Policy Management and Sociology. In August 2020, Kiley obtained two Microsoft certifications, Microsoft Office Specialist Excel 2016 and Microsoft Office Specialist PowerPoint 2016.