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Andrew O'Brien has a diverse work experience starting in 2000 with Virtual Strategy, Inc. as a Software Engineer. In 2003, they joined Trinity Wall Street where they held various positions including Applications Support Supervisor, Manager of IT Client Services, and Director of Business Systems. Additionally, they established their own consulting services, Andrew M. O'Brien Consulting Services, in 2005. Andrew'srole as a Consultant/Developer in this sole proprietorship continues to the present.

Andrew O'Brien completed their Bachelor of Arts degree in Psychology and Computer Science from Boston University from 1996 to 2000. Andrew later pursued further education by attending New York University from 2008 to 2009, where they obtained a Continuing Education certificate in IT Project Management. Additionally, Andrew also had some educational experience at LearningTree, although the specific details of their program or degree are unknown.