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Rebecca Gailing has a diverse work experience with various roles in different companies. Rebecca started their most recent job in 2020 at OceanFirst Bank as the Loan Operations Payment Team Lead. Prior to that, they worked as an Operations Specialist at Orbit Energy & Power, LLC in 2020. From 2017 to 2020, Rebecca was a Lead Preschool Teacher at Howell PAL Little PAL's Preschool. Rebecca also served as a Front Desk Manager at Play Cafe at Allaire Country Day from 2018 to 2019. Rebecca's longest tenure was at Allaire Country Day where they worked as a Head Counselor from 2010 to 2018. Rebecca also has experience in event coordination, having worked as an Event Coordinator at Playa Bowls from 2016 to 2017. Additionally, Rebecca has worked in various roles at festivals such as the Academy of Country Music Awards and Project Shelter in 2016, and FestWorks - TOMS Shoes at Red Frog Events in 2015. Prior to that, they worked as a Clubhouse Hostess at The Country Club at DC Ranch from 2014 to 2015.

Rebecca Gailing attended Brookdale Community College from 2010 to 2014, where they pursued a degree in Business Administration with a focus on Business Administration and Management. Rebecca then transferred to the W. P. Carey School of Business at Arizona State University and earned a Bachelor of Arts (BA) degree in Business Tourism Management from 2014 to 2016. In addition to their degrees, Rebecca also obtained certifications in Convention Sales & Meeting Planning and Special Events Management from the W. P. Carey School of Business at Arizona State University. The specific months and years of when they obtained these certifications are not provided.