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Anna McLain has a diverse work experience spanning over several years. Anna began their career as a Computer Geek at Computer 101 in 1994, where they worked until 1996. Anna then served as a Graduate Assistant at Florida State University from 2004 to 2005. Anna further gained experience as the Director of Belgrade Community Library from 2005 to 2006. Anna then worked as a Product Support Specialist at Zoot Technologies in Bozeman, MT from 2006 to 2007. Following this, Anna joined Yellowstone Club as a Systems and Purchasing Manager from 2007 to 2009. Currently, they are employed at Ascend Analytics since 2012, where they hold the position of IT Manager and Project Supervisor. In this role, they oversee the IT team, manages IT purchases and 3rd party accounts, and implements security procedures and protocols within the Azure AD environment.

Anna McLain obtained a Master of Library & Information Science (MLIS) degree in Information Technology from Florida State University in 2003. Prior to that, they earned a Bachelor of Science (BS) degree in Library and Information Science from the same university between 1995 and 1998. Anna McLain also attended Leon High School and Lincoln High School, although no specific degree or field of study information is available for those.