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Ann Pinkney has a diverse work history that spans over three decades. Ann began their career as a Graduate Intern at Burson-Marsteller in 1991. Ann then worked as an Account Representative and Assistant Account Executive before leaving the company in 1994. From 1994 to 1998, Ann held various communication roles at the Chicago Department of Cultural Affairs and the Chicago Historical Society. Ann then joined CKPR in 2000, starting as a Senior Account Executive and later becoming an Account Supervisor. Ann worked at CKPR until 2004 when they became a Freelance Writer/Editor. In 2006, they started their role as the Marketing Communications Director at Metropolitan Family Services, where they oversaw the implementation of strategic communications initiatives. In 2009, they were promoted to Senior Director, Marketing and Communications, a position they currently hold.

Ann Pinkney earned a Bachelor of Science in Journalism from Northwestern University from 1986 to 1990. Ann then went on to pursue a Master of Science in Corporate Public Relations from Northwestern University from 1990 to 1992. In 2013, they completed the Entrepreneurship Program and received a Certificate of Completion from The Joseph Business School.