After graduating from the University of Massachusetts, Rob attended the New England School of Law. He graduated Magna Cum Laude in 1997 and commenced his legal career as a trial attorney, and is experienced in complex civil litigation, criminal law, and real estate. He has tried many criminal and civil cases to completion in the Commonwealth's District and Superior Courts, he has represented clients in the Appeals Court and the Supreme Judicial Court, and he has negotiated numerous settlements and plea bargain arrangements with the Federal Bureau of Investigation and the office of the United States Attorney. Rob is admitted to practice before the state courts of Massachusetts, the United States District Court for the District of Massachusetts and the United States Court of Appeals for the First Circuit.

In 1999, he became an administrator of one of the first charter schools in the state of Florida. He went on in his career, to be a principal and school district administrator. He has been part of hundreds of child studies, and thousands of students' educational plans. He has trained teachers, principals and superintendents on compliance with special education laws, bullying prevention, student discipline procedures and curriculum innovations. He has supported school and school districts in student services' best practices. He has been a school board member, developing policy and performing governance of a school district. Will has been a member of local, state and federal committees that set policy regulations for schools. He is a certified evaluator for school accreditation. He utilizes all of his experience when he represents his clients. With such a broad knowledge in the educational field, Will is able to represent his clients in the most effective ways.