Tom represents businesses at the trial and appellate levels in complex disputes with government and with other businesses, and in insolvency matters.

He has successfully tried numerous cases in the United States District Court, Bankruptcy Court, and Superior Court. He has also won 18 cases before the Massachusetts Supreme Judicial Court, and argued four cases before the United States Court of Appeals for the First Circuit. Tom was selected by Massachusetts Lawyers Weekly as "Lawyer of the Year" for 2014 for establishing, in a case before the Supreme Judicial Court, the people's right to vote on whether to make casino gambling illegal in the state. In 2016, Massachusetts Lawyers Weekly chose to give him its award for excellence in pro bono service.

Tom's cases range from contract disputes to those involving fraud or negligence, as well as disputes with governmental entities. For example, Tom has represented:

• A medical marijuana business appealing de-selection of its registration by the Department of Public Health
• A Fortune 50 company for over a decade in litigation and bankruptcy dealing with financially distressed suppliers
• A major financial institution in cases brought by the Massachusetts Attorney General and others arising out of the mortgage banking crisis

Tom was appointed in 2011 by the Massachusetts Supreme Judicial Court to investigate and prosecute wrongdoing by the clerk-magistrate of a district court, an appointment that led to the clerk's removal from office.

Prior to joining Verrill, Tom practiced at the Boston office of an international law firm with 1,100 attorneys. Before that, he served as a Massachusetts assistant attorney general in the appellate and trial divisions.

Tom serves on the National Advisory Board of the John C. Danforth Center for Religion and Politics at Washington University in St. Louis, and was elected by his peers to serve on the Council of the Boston Bar Association. He was appointed by the Massachusetts Supreme Judicial Court to the Client Security Board in 2005; that board hears claims brought by individuals who maintain that their lawyers stole money from them and frequently makes awards of reimbursement. He served as co-chair of the Bankruptcy Section of the Boston Bar Association from 2001 to 2003. He is a member of the American Bankruptcy Institute and lectures frequently on litigation, appellate, and bankruptcy matters.

Tom is a teacher by training and at heart. He taught middle school and high school after graduating from college, and has taught college, business school, and law school courses since becoming a lawyer. He is the co-founder of Spark Academy, a public middle school in Lawrence, Massachusetts, that intertwines academics and physical activity throughout an extended school day. Tom chairs the school's advisory board, and manages fundraising and publicity for the school. Tom also developed the idea for, helped develop the curriculum for, and taught classes to middle school students on search and seizure in public schools through Discovering Justice.