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Anne Stillson has a diverse work experience spanning over several years. Anne started their career at Walgreens in 1995 as an Associate and worked there until 1997. Anne then joined Sears Hardware as a Customer Service Representative for a brief period before moving to Computer City as a Customer Service Representative in 1998. Later that year, they transitioned to Gateway as a Sales Consultant, where they worked until 2000. In 2000, they joined David's Bridal as a Sales Consultant for a short duration. Anne then joined the City of Naperville in 2008 and held various roles, including Geographic Information Systems Technician and Geographic Information System Specialist. Currently, they are serving as a Project Manager in the same organization.

Anne Stillson obtained their Bachelor of Science (B.S.) degree in Geography from Northern Illinois University in 2009. Prior to that, they earned an Associate of Arts (A.A.) degree with Honors in Liberal Arts & Sciences from the College of DuPage in 2004. Anne also attended Western Illinois University in 1996-1997, where they studied Geography. The degree obtained at Western Illinois University is not specified.