Olivia Ajero is an Associate Attorney at DDV Law, Ltd., where she represents older adults, individuals with disabilities, children with special needs, and their families in matters involving elder law, special needs planning, guardianships, trust and estate administration, Medicaid planning, and educational advocacy. Olivia brings both compassion and determination to her work and is deeply committed to helping individuals with disabilities access the services, protections, and opportunities they deserve.
Olivia has developed a strong passion for advocating for children and young adults with disabilities as they navigate the educational system. She works with families to secure appropriate Individualized Education Programs and Section 504 plans so that students receive the accommodations, therapies, and educational support necessary for success. Olivia understands that strong advocacy during a child's educational years is often the foundation for long term independence, stability, and access to services in adulthood. She approaches these matters with both legal skill and a deep appreciation for the challenges families face when working with school systems.
She is also highly dedicated to guardianship advocacy and the protection of individuals who cannot protect themselves. Olivia understands the profound responsibility that guardians and the courts carry in safeguarding vulnerable individuals, and she approaches these matters with empathy and precision. She works closely with families to navigate guardianship proceedings while ensuring that individuals with disabilities maintain dignity, respect, and protection.
Olivia has a particular interest in trust and estate administration and enjoys guiding families through the process of carrying out a loved one's wishes. She appreciates the detailed and strategic nature of administering trusts and estates and works diligently to ensure that fiduciaries understand their responsibilities while helping families move through what is often a difficult time with clarity and confidence.
She is also especially passionate about helping seniors and individuals with disabilities navigate the Medicaid system, which can often create significant and sometimes discriminatory barriers to care. Olivia believes strongly that careful legal planning can help families preserve resources while still qualifying for essential benefits. Through thoughtful Medicaid and special needs planning strategies, she helps families protect financial stability while ensuring access to critical healthcare and long term care services.
Olivia comes from a family deeply committed to public service and caring for their community, particularly older adults. That background shaped her commitment to advocacy and her dedication to serving seniors, children with disabilities, and families navigating complex legal systems.
Olivia earned her Juris Doctor from DePaul University College of Law in 2025, where she focused on estate planning, special needs law, and family law. She has been admitted to the Illinois State Bar. She earned her Bachelor of Science in Psychology with a minor in Political Science from Southern Illinois University Edwardsville while remaining active in student leadership and community engagement.
While at DePaul, Olivia founded Law Students Supporting Neurodiversity and served as Co President for two years. Through this organization she helped law students understand and obtain accommodations for both law school and the bar examination while also organizing educational and mental wellness programming. Her leadership also helped establish a dedicated seat on the student Diversity, Equity, and Inclusion Committee. Olivia also served as Secretary of the Women's Bar Association student chapter, helping foster mentorship, networking, and professional development opportunities for law students.
Outside of her legal work, Olivia enjoys attending concerts, crocheting, exploring Chicago neighborhoods, and spending time with her two cats.
