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Andrew Sinclair has a diverse work experience, starting with their role as a Business Education Coordinator at the Small Business Development Center of Hampton Roads, Inc. from January 2004 to March 2005. Andrew then worked as a Membership Coordinator at the Hampton Roads Chamber of Commerce from March 2005 to March 2006. Following this, they joined the Hampton Roads Partnership as a Program Specialist from March 2006 to October 2008, and later became a Program Manager from October 2008 to June 2011. Andrew then worked as the Government Affairs Director at Organization Management Group Inc. from July 2011 to July 2014. Andrew joined the Port of Virginia as the Director of Government Affairs from August 2014 to July 2016, and then transitioned to the role of Director of Federal Government Affairs from July 2016. Additionally, Andrew volunteered for the Boy Scouts of America from June 2000 to March 2015.

Andrew Sinclair attended Kempsville High School, but the duration of their education there is not provided. In 2000, they enrolled at Hampden-Sydney College and completed their Bachelor's degree in Philosophy and Religion in 2003.