Attorney Raymond Dinsmore graduated cum laude from Western New England College School of Law in 2006. He was a member of the school's Law Review and served as an Assistant Editor in 2005. He also performed internships at Western Mass Legal Services in Northampton, Massachusetts and Springfield, Massachusetts. Dinsmore graduated cum laude from the University of Massachusetts, Amherst in 2002 majoring in history.

Attorney Dinsmore worked as an attorney for Western Mass Legal Services in Northampton, Massachusetts in 2006 and 2007, practicing primarily in employment law. Dinsmore formed the Law Office of Raymond Dinsmore in January 2008. He is licensed to practice law in the Commonwealth of Massachusetts, the Federal District Court of Massachusetts, and the District of Massachusetts Bankruptcy Court. Attorney Dinsmore is also a Massachusetts licensed real estate broker with Norwottuck Real Estate Company in Amherst, Massachusetts