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

Entyre & Pflegewegweiser•Chicago, IL

31d

About The Position

Entyre Care is a high-growth start-up organization geared to success in Home and Community-Based Services (HCBS). As we continue the advancement of healthcare in homecare, we are seeking driven, motivated candidates that are excited to join a fast-paced environment. We are hiring an Customer Success Specialist to serve as a main point of contact for prospective and existing clients who call, text, or leave voicemails with questions about Entyre Care’s program. This is not a passive customer service role. The right person will be warm, clear, and highly organized, while also having the judgment and sales instincts to move clients to the next step. Many families we support are navigating healthcare, Medicaid, documentation, reimbursement, training, and onboarding requirements for the first time. This role requires someone who can explain complicated processes simply, build trust quickly, and keep clients moving forward. You will own communication, assess client needs, answer questions, document interactions accurately, and coordinate with internal teams when issues need escalation.

Requirements

1–3 years of experience in sales, customer service, healthcare administration, client intake, call center operations, client support, or a related role.
Strong verbal and written communication skills, with the ability to explain complex processes clearly and professionally.
Personable, empathetic, and confident on the phone.
Strong follow-up instincts and comfort guiding clients toward a decision or next step.
High attention to detail and ability to maintain clean, accurate records.
Organized and able to manage multiple client conversations, tasks, systems, and deadlines at once.
Comfortable working in a fast-paced environment with frequent interruptions and shifting priorities.
Strong problem-solving skills, including the ability to identify the real issue behind a client’s question.
Comfortable navigating multiple systems, databases, spreadsheets, and web-based platforms.
Able to handle sensitive or confidential information with professionalism.
Proficiency with Microsoft Office, Google Workspace, CRM systems, or similar tools.
Ability to work flexible hours or overtime as business needs require.

Nice To Haves

Familiarity with Medicaid, healthcare services, waivers, billing, compliance, or reimbursement processes is preferred but not required.
Associate’s or bachelor’s degree preferred, or equivalent relevant experience.

Responsibilities

Serve as the primary point of contact for calls, voicemails, text messages, and client inquiries.
Build rapport quickly with prospective and current clients by being warm, professional, and clear.
Assess client needs, determine eligibility-related next steps, and guide clients through the onboarding process.
Use strong follow-up and sales instincts to encourage clients to complete required steps, submit documents, schedule appointments, or move to the next stage.
Explain Entyre Care’s program, Medicaid waivers, service appointments, billing, background checks, reimbursement expectations, and related processes in a way clients can understand.
Manage high-volume communication while maintaining accuracy, professionalism, and urgency.
Track client status, next steps, open issues, and follow-up needs in the appropriate systems.
Maintain accurate and up-to-date client contact information, records, notes, and documentation.
Identify issues, troubleshoot basic problems, and escalate appropriately to Billing, Compliance, Admin, Clinical, or other internal teams.
Coordinate communications related to payment discrepancies, discharges, reimbursement procedures, and other client-facing operational issues.
Manage existing client scheduling
Follow established processes while using good judgment when situations are unclear or complex.
Help improve scripts, workflows, FAQs, and communication processes as recurring client questions or bottlenecks arise.