Justin B. Cary

Justin B. Cary is an attorney at Drummond Woodsum in Portland, Maine, who primarily represents schools, nonprofits, Tribal Nations, and small businesses. His practice focuses on artificial intelligence and technology, labor and employment, constitutional rights of employees and students, school and education law, and compliance with state and federal requirements. He advises clients on emerging legal questions while connecting technology decisions with employment, policy, contractual, and regulatory considerations.

Justin earned a J.D. magna cum laude from the University of Maine School of Law and a B.A. magna cum laude from Colby College. His legal education included recognition in business and transactional law. That academic background supports a multidisciplinary practice involving contracts, employment issues, school operations, emerging technology, and regulatory compliance. He applies that training to novel questions where traditional legal frameworks must be considered alongside rapidly changing technology and organizational needs.

Justin advises clients on generative artificial intelligence through contract drafting and negotiation, policy development, workplace audits and investigations, compliance counseling, and technology training. His employment practice includes investigations, misconduct allegations, wage-hour matters, employee mobility, leave issues, mediation, arbitration, and administrative proceedings. He also works on collective bargaining and provides training to public, private, and tribal entities. He serves on Maine’s Artificial Intelligence Task Force as a subject-matter expert on legal issues presented by AI.

Justin B. Cary has been recognized by Best Lawyers as an Ones to Watch honoree in Technology Law for 2026 and by New England Super Lawyers as a Rising Star for 2025 and 2026. His pro bono work has included unemployment matters, small claims representation, and protection-from-abuse proceedings. He combines technology, employment, education, and business experience to help organizations address new legal risks while maintaining practical policies and operations.

Law Office Affiliations

• Attorney, Drummond Woodsum
• Member, Maine State Bar Association
• Governing Board, New Lawyers Section for Maine State Bar Association
• Firm Director of Associate Fundraising, Campaign for Justice
• Member, Maine Counsel for School Board Attorneys
• Litigation Volunteer, Volunteer Lawyer Project
• Volunteer Lawyer, Small Claims Clinic
• Member, Drummond Woodsum Community Service Committee
• Former Member, AmeriCorps

Licensed State

• Maine

Education

• University of Maine School of Law
  Juris Doctor (JD) (Magna Cum Laude)
• Colby College
  Bachelor of Arts (BA) (Magna Cum Laude)

Awards & Badges