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Hailey Whitehead's work experience includes various roles in different companies. Hailey worked as a Sourcing Center Supervisor at Apex Service Partners starting from February 2023. Prior to that, they were employed at Ascendo Resources where they held multiple positions. These roles include Managing Director from April 2022 to January 2023, Senior Executive Recruiter in April 2022, and Executive Recruiter from September 2021 to April 2022. Before joining Ascendo Resources, Hailey worked at CareerStaff Unlimited as a Healthcare Recruiter from September 2020 to September 2021, and as an Operations Coordinator from April 2020 to September 2020. Their earliest work experience was at Publix Super Markets as a Customer Service Staff from December 2014 to December 2020. Additionally, they were also an Executive Recruiter, specializing in Accounting & Finance in the Orlando division at Ascendo Resources from February 2020 to March 2020.

Hailey Whitehead completed their education in a chronological order, beginning with their enrollment at Florida Gulf Coast University from 2016 to 2018. During this time, they earned an Associate of Arts degree in Psychology. Following this, they pursued higher education at the University of Central Florida from 2018 to 2020, receiving a Bachelor of Science degree in Psychology.