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Rachel Caldwell has a diverse work background, starting with their role as a Teacher at St. Mary's High School from 2000 to 2004, where they taught English, Religion, Special Education, and Career Studies. Rachel then worked at the University of Waterloo as an Associate in Library Communications & Information Services from 2004 to 2007. Following that, they held the position of Senior Research Officer at McMaster University from 2007 to 2009. From 2005 to 2009, Rachel was self-employed as a freelance Prospect Researcher. Since 2009, they have been working at Conestoga College, initially as an Information Services Coordinator from 2009 to 2012 and currently as the Manager of Customer Experience & Operations. In this role, they oversee in-person and online frontline library services, staff training, facilities planning, and maintenance for six campus locations. Rachel also assists in coordinating and delivering library-related events and had a previous part-time secondment with the Centre of Applied Research & Innovation (CARI) at Conestoga College to help with grant writing and research.

Rachel Caldwell obtained a Bachelor of Arts (BA) degree in English Literature & Italian from the University of Waterloo - St. Jerome's University, where they studied from 1995 to 1999. Rachel furthered their education at Brock University and earned a Bachelor of Education (BEd) degree from 1999 to 2000. Later, they pursued a Master of Library & Information Science (M.L.I.S.) degree at Western University from 2003 to 2005.

In addition to their formal education, Rachel Caldwell has obtained several certifications throughout their career. Rachel completed a course on "How to Research and Write Using Generative AI Tools" at LinkedIn in April 2023. In May 2021, they obtained a certification titled "Balancing Multiple Roles as a Leader" from LinkedIn. Rachel also holds certifications in "Coaching Skills for Leaders and Managers," "Leading Remote Projects and Virtual Teams," and "Learning Data Governance," all from LinkedIn, which they obtained in December 2020 and September 2020. Prior to that, they completed a course on "Grant Writing for Education" at Lynda.com in February 2017. In terms of First Aid training, they are "First Aid & Adult CPR Certified" by Emergency Care Instruction Services since May 2014. Rachel Caldwell also has a certification in "Project Management for Professionals" from McMaster University, obtained in 2008, and "Writing for Public Relations and Marketing" from the University of Waterloo in 2006.