Entitlement Specialist

Help Families Access the Resources They Need

$27.02/Hour

THE ROLE

Win is seeking a dedicated Entitlement Specialist to support families on their path toward housing stability and self-sufficiency. In this role, you will serve as a key liaison between clients and government agencies, helping families secure critical public benefits, navigate complex entitlement systems, and access the resources they need to achieve long-term success. You will combine advocacy, case support, financial education, and client engagement to help remove barriers and strengthen outcomes for families experiencing homelessness.

What You Will Do

• Screen clients for eligibility and connect them to available public and private benefits programs
• Assist clients with benefit applications, recertifications, appeals, and ongoing entitlement maintenance
• Serve as a liaison between clients and government agencies, including HRA, Social Security, and other service providers
• Escort clients to appointments and advocate on their behalf to ensure timely access to services and benefits
• Prepare families for successful rehousing through financial education, benefits planning, and resource navigation
• Maintain accurate client records and documentation using CARES and Win's data management systems
• Facilitate weekly group sessions that educate and empower clients on available resources and benefits
• Prepare required reports and ensure compliance with agency, funder, and program documentation standards

Who You Will Be

• You will hold a bachelor’s degree in human services or a related field
• You will have experience navigating entitlement systems, public benefits programs, and government service processes
• You will possess excellent organizational, written, and verbal communication skills
• You will have experience working with individuals facing mental health challenges and other barriers to stability
• You will demonstrate strong advocacy and client engagement skills, with the ability to build trust and rapport with diverse populations
• You will have solid computer proficiency, including Microsoft Office applications and Outlook
• You will be able to manage competing priorities and maintain accurate records for a high-volume caseload
• You will have bilingual English/Spanish skills (preferred)