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

• 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)

Bachelors or better.

Equal Opportunity Employer
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