Associate Attorney - Planning, Care & Benefits

About the Role
Dillman & Owen Estate and Elder Law is a well-established law firm seeking a compassionate, detail-oriented Associate Attorney to join our Planning, Care & Benefits Team. This role is ideal for an attorney who is passionate about elder law, estate planning, and helping families navigate long-term care, benefits, and aging-related challenges.

You will work closely with senior attorneys, Client Care Advocates, and team members across practice areas to provide exceptional legal services to older adults and their families—while developing deep expertise in estate planning, Medicaid, VA benefits, and life-care planning.

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What You’ll Do

Client Representation & Legal Work

• Develop personalized life care plans for clients, including financial, medical, and legal components.
• Support the Life Care Planning team by assisting clients and families with issues involving long-term care, quality of care, family conflict, crisis situations, Medicaid planning, and healthcare decision-making.
• Draft, revise, and review estate planning documents, including Revocable Trusts, Wills, Asset Protection Trusts, Special Needs Trusts and Advance Directives.
• Assist with Medicaid and Veteran’s benefits cases, including eligibility analysis, application preparation, appeals, and related planning.
• Participate in client meetings, review meetings, and funding meetings alongside attorneys and care coordinators.
• Conduct legal research and stay updated on changes in elder law, Medicaid/Medicare rules, tax considerations, and estate planning best practices.

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Team Collaboration & Case Management

• Manage an active caseload with strong organization and time-management skills.
• Work collaboratively with Life Care Planning, Estate Planning, and Benefits team members to ensure excellent client service across the lifecycle of a case.
• Provide peer support through drafting, reviewing documents, and maintaining firm standards of accuracy and quality.
• Communicate with clients and families during emotionally challenging circumstances with empathy, clarity, and professionalism.

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Professional Growth & Firm Culture

• Contribute to a positive, supportive, team-oriented culture where all employees feel valued.
• Participate in internal trainings, mentorship, and cross-department collaboration.
• Attend marketing, networking, and educational events as needed to support practice-area growth.
• Bring creative ideas to improve processes, client experience, and service offerings as the department evolves.

What We’re Looking For

Required Skills & Abilities

• Excellent legal writing and communication skills.
• Strong understanding—or demonstrated ability to quickly learn—relevant laws, including:
   
  • Estate planning (trusts, wills, Special Needs Trusts, etc.)
   
  • Elder law
   
  • Medicaid / Medicare
   
  • Healthcare decision-making
• High emotional intelligence and empathy for clients navigating aging, disability, and family conflict.
• Ability to analyze complex situations and propose practical, creative solutions.
• Strong attention to detail, time management, and organizational skills.
• Comfort with technology, including Microsoft Office Suite and cloud-based case management tools.
• Ability to take and implement feedback in a collaborative environment.
• Commitment to client confidentiality and ethical practice.
• Growth mindset and eagerness to expand knowledge in elder law and benefits planning

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Education & Experience

• Juris Doctor (JD) from an accredited law school
• Licensed to practice law in Indiana
• 1–3 years of legal experience preferred, ideally in estate planning, elder law, family law, healthcare law, or related fields
   
  • Newer attorneys with strong writing, empathy, and interest in elder law will  also be considered

Why Join Our Firm?

• Mission-driven work that makes a direct impact on older adults and families during critical life moments.
• Supportive team environment with mentorship, training, and opportunities for growth.
• Competitive compensation package with benefits, PTO, and professional development support.
• A collaborative culture that values innovation, compassion, and high-quality service.

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If you are interested in this position, please submit your resume and writing samples to mariapage@dillman-owen.com.

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