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Anna Oakley's work experience includes a role as a Marketing Manager at Craig Industries starting in May 2021. Prior to that, they worked as a Customer Service Representative at HOMEBANK from July 2019 to May 2021. From November 2017 to July 2019, Anna worked as a Web Content Specialist at QUINCIFY. Anna also had experience as a Program Outreach Intern at the Community Foundation Serving West Central Illinois and Northeast Missouri from April 2017 to November 2017. Anna gained further experience as a Communication Specialist-Intern at the Quincy (IL) Area Chamber of Commerce from December 2015 to December 2016. Before that, they worked as a Circulation Coordinator at the Herald-Whig from August 2013 to December 2015. Other positions held by Anna include an Au Pair at Frederique LeGreves from July 2014 to August 2015, Copywriter Intern at Virginia Living from August 2012 to December 2012, and Quintern at the Herald-Whig from June 2012 to September 2012. Anna's earliest work experience was as a Corps Member at City Year, where they completed over 1800 hours of service focused on literacy and education from September 2009 to June 2010.

Anna Oakley attended Quincy University from 2015 to 2017, where they obtained a Bachelor's Degree in Communication and Media Studies. In addition to their degree, Anna also obtained several certifications, including a Learning LinkedIn certification from LinkedIn in April 2018, an Email Marketing Certification from HubSpot in March 2018, and various certifications from HubSpot Academy, Hootsuite, and Hootsu, although the specific dates and details for these certifications are unknown.