David O'Reilly has extensive work experience, starting in 1981 as the Finance Director for The Massachusetts State Lottery Commission. In this role, they managed various projects, including a successful campaign to raise awareness about litter and recycling. From 2003 to 2005, they also served as the Claims / Season Ticket Manager, overseeing high tiered prizes and disputed claims. In 2012, they became a Union member and Chairman for the Service Employees International Union, Local 888, where they played a key role in negotiating a new contract and promoting a safe work environment. Additionally, since 1998, they have been a valued member and former Chairman of the Plymouth County Democratic League, working on successful political campaigns for state Treasurer candidates.

David O'Reilly attended Massasoit Community College from 2001 to 2005, where they pursued their Associates degree in Marketing/Business. In 2002, they briefly attended U-Mass Boston for a program in Mid-Level Management Development with a focus on Business/Marketing. Earlier in their education, from 1981 to 1984, David attended U-Mass Boston and Bridgewater State, although the degree name and field of study for this period are not specified.

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