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Taylor Connolly has a diverse work experience in various roles in public affairs, public relations, communications, and community engagement. They are currently working as the Senior Director of Public Affairs & Public Relations at The Castle Group since 2022. Prior to this, they served as the Communications Director for John Barros for Mayor from May 2021 to December 2021. Additionally, they worked in multiple roles at the City of Boston, including Director of Communications & Community Engagement from August 2020 to May 2021, Communications Manager at the Mayor's Office of Economic Development from September 2016 to August 2020, and Special Assistant at the Mayor's Office of Sports, Tourism, & Entertainment from December 2014 to September 2016. Taylor also has experience as an Account Executive and Account Coordinator at Rasky Partners from April 2013 to December 2014 and December 2011 to April 2013, respectively.

Taylor Connolly attended Union College from 2007 to 2011 and obtained a Bachelor of Arts degree. The degree focused on the fields of English and History.