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Kaila Kowalski has a diverse work experience, starting from 2009 at Florida State University, where they held multiple roles including Resident Assistant, Orientation Leader & Office Staff, Dance Marathon Internal Director, Greek Life Intern, and C.A.R.E. Counselor. Kaila then worked as a NODA Intern at Radford University New Student Programs in 2013 and as a Regional Conference Committee Social Media Intern at NASPA - Student Affairs Administrators in Higher Education Region IV-E in the same year. From 2012 to 2014, Kaila worked as a Graduate Hall Director at Bowling Green State University Office of Residence Life and as a Resident Director at Florida Gulf Coast University from 2014 to 2017. Kaila then joined the University of Central Florida as Coordinator of Staff Selection & Student Leadership from 2017 to 2019, and later became an Assistant Director Of Residence Life - Staff Recruitment & Leadership from 2019 to 2021. Kaila also had involvement with the SOUTHEASTERN ASSOCIATION OF HOUSING OFFICERS, where they served as Marketing & Organizational Promotions Committee Chair from 2016 to 2018, Marketing Chair for SEAHO 2019 Conference from 2017 to 2019, and Chair of Website, Technology, & External Communications Task Force from 2019 to 2020. Currently, they are working at IZEA, starting as a Manager, Workplace Culture & Communications from 2021 to 2022, and now as the Director, Workplace Culture & Communications from 2023.

Kaila Kowalski obtained their Bachelor of Arts degree in Media Production with a Leadership Studies Certificate from Florida State University in the years 2008 to 2012. Kaila then pursued a Master's degree in College Student Personnel at Bowling Green State University from 2012 to 2014. In 2021, Kaila obtained additional certifications, including "Building a Stellar Employee Experience," "Diversity, Inclusion, and Belonging," and "Supporting the Whole Self at Work, a Diversity and Inclusion Imperative" from LinkedIn.