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Kaylee Estes began their work experience in 2013 at Prestige Staffing, where they started as a Senior Technical Recruiter and eventually grew into the role of Recruiting Manager for Technical Recruiting. During their time there, they managed teams of technical recruiters and specialized in recruiting for various positions in the software development life cycle. From 2017 to 2019, Kaylee worked at Gather as the first Recruiting Manager, overseeing a Recruiting Team and leading talent strategy during the company's hyper-growth phase. In 2020, they joined Greenlight as a Senior Recruiter and later transitioned to Senior Manager of Recruiting, before becoming the Director of Talent Acquisition. At Greenlight, Kaylee was responsible for managing a global recruiting team and overseeing the company's recruiting strategy, operations, tools, and employer branding. In 2023, they founded Estes Group, LLC., a talent strategy firm that provides staffing, fractional recruiting, talent strategy, and career services for startups and growing teams.

Kaylee Estes completed their education at Auburn University, where they earned a Bachelor of Science degree in Human Development & Family Studies. Kaylee attended Auburn University from 2007 to 2011. Prior to that, Kaylee Estes completed their high school education at Blessed Trinity Catholic High School. The duration of their high school education was from 2002 to 2006. However, there is no specific degree or field of study mentioned for their high school education.