Aylesworth is a civil litigator with 20 years of experience representing clients in the state and federal courts in New Hampshire and Massachusetts. While attending Boston College Law School, Aylesworth served as an intern on the Constitutional Subcommittee to the Senate Judiciary Committee in Washington, D.C., and he assisted attorneys on matters before the United States Supreme Court. Prior to law school, Aylesworth taught high school English in public schools in his home state of Wisconsin.