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Ronald Sheehan has a diverse work experience spanning over several years. Ronald started their career as a Paralegal at the Office of the MA Attorney General in 1992, where they worked until 1999. Ronald then joined One Communications in 1999 and served as their Regulatory Compliance Manager until 2007. In this role, they managed a team of five and was responsible for writing, developing, modifying, and managing various tariffs. From 2007 to 2018, Ronald worked at iBasis Inc. as the Senior Manager of Contracts. Here, they successfully managed a team of four and played a key role in designing and developing the company's Contract Management System. Currently, Ronald is the Director of Regulatory Compliance at Fusion Connect, a position they have held since 2018.

Ronald Sheehan attended Berklee College of Music from 1983 to 1988, where they pursued a Bachelor's degree in Music. During their time at Berklee, they dual majored in Jazz Composition and Arranging as well as Music Education. After a gap of several years, from 1995 to 1996, Ronald attended UMass Boston. Although no specific degree is mentioned, they studied Mathematics and Finance during this period.