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Caitlin Regan began their career in 2010 as a Teaching Assistant at Acadia University, where they facilitated class discussions, assisted with assignments, and oversaw a mock-government simulation. Caitlin then served as the Vice President for Student Affairs and Executive Vice President at Acadia Students' Union from 2009 to 2011, during which they acted as the Bar Manager. From 2011 to 2013, Caitlin worked as an Administrative Assistant at Dalhousie Student Union. In 2014, they joined Cox & Palmer as an Articled Clerk, eventually becoming a Lawyer and working there until 2021. Currently, Caitlin is the Director of Risk and Legal at Lindsay Construction, a role they started in August 2021.

Caitlin Regan has a strong education background. Caitlin attended Charles P. Allen High School, but the specific dates are unknown. After completing high school, they pursued higher education at Acadia University from 2006 to 2011. During their time at Acadia, they obtained a Bachelor of Arts (B.A.) with Honours, majoring in Political Science. Following this, they attended Dalhousie University from 2011 to 2014, where they earned a Doctor of Law (JD) degree, specializing in Law.