Jessica S. Gillespie

Jessica S. Gillespie is a family law attorney with deep roots in the field, shaped by both personal experience and professional dedication. As a child of separated parents, she understands how overwhelming and emotionally charged these situations can be. That insight fuels her commitment to offering clients a different path – one rooted in dignity, empathy, and resolution.

Jessica earned her B.A. from St. Mary’s College of Maryland and her J.D. from the University of Baltimore School of Law. During law school, she spent two semesters in the Bronfein Family Law Clinic, working directly with clients on real-world family law matters, and was on the Family Law Moot Court Team. After graduation, she served as a Judicial Law Clerk to The Honorable Magistrate William M. Dunn in the Family Division of the Baltimore City Circuit Court – an experience that deepened her understanding of the court system and its impact on families.

She is collaboratively trained and mediation certified, with a practice focused on helping families move forward – not fall apart. Whether working through divorce, parenting arrangements, or other complex transitions, Jessica offers a steady hand and a client-centered approach rooted in respect, clarity, and long-term solutions.

Outside of the office, Jessica loves traveling the world with her husband, cheering on her favorite Philadelphia sports teams (go Birds!), and spending time with their three beloved dogs. She brings the same loyalty, energy, and kindness to her practice that she brings to the rest of her life.

Legal expertise matters – but so does heart. Jessica brings both.