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Caitlin O'Brien has a diverse work experience across multiple industries. Caitlin started their career as a Wealth Management Intern at Morgan Stanley Smith Barney in 2009. Caitlin later served as an Operations Intern at New York Life Insurance Company from 2009 to 2010. Caitlin then worked as an Archives Aid at the U.S. National Archives and Records Administration from 2008 to 2010. Caitlin joined Marley Properties in 2010, where they held a role in the Office of Finance and Administration until 2012. Caitlin then transitioned to JLL, where they worked as a Senior Accountant, Construction from 2012 to 2017. Caitlin moved to Turnstyle Cycle in 2016 and held the position of Cycle Instructor until 2022. Most recently, Caitlin has been serving as the Director of Financial Operations at Corderman & Company, Inc. starting in October 2017.

Caitlin O'Brien holds a Bachelor of Science degree in Economics-Finance from Bentley University. Additionally, they have obtained a Master of Business Administration (MBA) with a specialization in Real Estate Management from Bentley University - McCallum Graduate School of Business. In terms of certifications, Caitlin has completed the Transformational DEI Certificate program offered by the Greater Boston Chamber of Commerce. As a result, they are recognized in the field of diversity, equity, and inclusion. Furthermore, Caitlin is a certified Notary Public in the State of Massachusetts. The specific dates of completion for the certifications, as well as any obtained month for the Transformational DEI Certificate, were not provided.