Customer Success Specialist – Up to $2,000 Sign-On Bonus!

Entyre Inc is seeking a Customer Success Specialist in Chicago, Illinois to serve as the frontline contact for families enrolling in home and community-based healthcare services. In this full-time role, you'll manage inbound calls, texts, and voicemails—combining empathy with problem-solving to guide clients through Medicaid, eligibility verification, onboarding, and billing.

What This Role Involves

This position demands more than typical customer service delivery. You'll be the trusted guide helping families navigate complex healthcare processes, eligibility requirements, and reimbursement for the first time. You'll listen to understand each family's situation, explain Entyre's programs clearly and professionally, identify barriers, and use follow-through and sound judgment to keep momentum alive. Many clients encounter Medicaid documentation, service activation, compliance checkpoints, and financial planning for the first time—your clarity and persistence are essential.

Your Responsibilities

• Manage all incoming client outreach via phone, text, voicemail, and email
• Establish trust and professional rapport in initial client conversations
• Identify client needs, barriers, and eligibility pathways to guide enrollment
• Explain service programs, Medicaid waivers, billing structures, background checks, and onboarding procedures in accessible language
• Follow up consistently to keep clients engaged in completing required tasks and documentation
• Maintain detailed, accurate records of client interactions and status
• Handle concurrent client communications while maintaining quality and urgency
• Troubleshoot issues and escalate to Billing, Compliance, Clinical, or Administrative teams as needed
• Coordinate communications around payment discrepancies, service transitions, and operational questions
• Manage appointment scheduling for existing clients
• Suggest process improvements as patterns in client questions or bottlenecks emerge
• Follow established procedures while applying judgment in ambiguous or complex scenarios

Skills & Qualifications

• 1–3 years of experience in customer service, sales, healthcare administration, call center operations, or client intake
• Excellent verbal and written communication; ability to simplify complex healthcare and regulatory concepts
• Personable and confident in phone interactions; genuine empathy and professional presence
• Strong follow-up mindset; comfort guiding clients toward needed actions
• High attention to detail and commitment to accurate record-keeping
• Strong organizational ability; capacity to juggle multiple priorities and deadlines
• Adaptability in fast-paced environments with frequent interruptions and shifting focuses
• Strong problem-solving skills and ability to identify the core issue in client questions
• Comfort using multiple software platforms: Microsoft Office, Google Workspace, CRM systems, databases
• Ability to manage sensitive personal health information with confidentiality
• Familiarity with Medicaid, healthcare services, waivers, or reimbursement processes is helpful but not required
• Flexibility for variable hours or overtime when needed
• Associate's or bachelor's degree preferred, or equivalent professional background

About Entyre Inc

Entyre Inc is a healthcare startup committed to expanding access to quality home and community-based services while simplifying the operational complexity families and providers face. Founded on values of excellence, speed, and ownership, Entyre attracts mission-driven professionals who want to meaningfully impact families' access to care and wellbeing.

Next Steps

To apply, complete your application directly on this page, or you'll be redirected to the employer's application platform to finish submitting there.