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Chiffawn J. has a diverse work experience spanning across various roles in human resources and administration. They started their career as an Administrative Assistant at Adler Pollock & Sheehan P.C. in 2003, and then moved on to work as an Administrative Assistant at CRICO from 2005 to 2007. In 2009, they joined YouthBuild USA, where they progressed from being a Human Resources Assistant & Office Manager to a Human Resources Generalist & Office Manager, and finally to a Talent Acquisition Manager. At YouthBuild USA, Chiffawn developed and implemented talent acquisition strategies and best-in-class recruitment practices. Since 2017, they have been working at HopeWell Inc, first as a Human Resources Manager and currently as the Director of Talent Engagement and Recruitment.

Chiffawn J. has a Certification in Talent Acquisition Strategy from the Human Capital Institute (HCI), a Certification in FMLA Master Class from HRhero, and a Certification in Human Resources Basics from the Society for Human Resources Management (SHRM). They also attended Newton South High School and received training in Public Speaking from the TM School. Additionally, Chiffawn J. holds additional certifications in FMLA Master Class from HRHero in 2013, E-Verify from the US Department of Homeland Security in 2013, and HR Generalist from SHRM in 2011.