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Diana Farrell began their work experience in 2002 as an Assistant Branch Manager at Citizens Bank. In this role, they focused on building customer relationships, resolving issues, and overseeing a team of employees. From 2004 onwards, they joined Delaware Transit Corporation, starting as an HR Specialist responsible for administration of employee benefits and the company's Drug & Alcohol program. Diana then moved up to become the Benefits Administration Manager and eventually became the Chief Human Resources Officer in June 2017.

Diana Farrell holds a Bachelor of Science (BS) degree in Sociology from the University of Delaware. Additionally, they earned a Master of Public Administration (MPA) degree from Wilmington University. However, the specific years of their education are not provided.