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Medicare Retention Specialist (Support Services) – Fully Remote (1099 Independent Contractor)

February 5, 2026

Medicare Retention Specialist (Support Services)

Company Overview

[Company Name] is a Medicare-focused health insurance agency committed to delivering an exceptional member experience. We support Medicare-eligible clients with guidance, service, and ongoing plan support. We’re hiring a Medicare Retention Specialist (Support Services) to strengthen client relationships, resolve issues, and improve satisfaction—without sales responsibilities.

Position Summary

In this role, you’ll work with existing clients to address concerns, resolve service issues, and provide benefits support that helps clients feel confident and cared for. This is a support-services-only retention position focused on client advocacy, problem-solving, and follow-through.

This is a fully remote, 1099 independent contractor position.

Key Responsibilities (Support Services Only)

Provide inbound and outbound retention support to existing Medicare clients (check-ins, follow-ups, and issue resolution).
Identify and address churn risk drivers (billing questions, ID card requests, plan/benefit confusion, provider/pharmacy concerns, authorization/referral questions, etc.).
Deliver clear, empathetic guidance and de-escalation to resolve client dissatisfaction and improve outcomes.
Coordinate with internal teams and carrier partners to resolve service issues and escalations.
Track open issues through to completion and communicate updates to clients in a timely manner.
Document every interaction accurately in CRM/agency systems, including actions taken and next steps.
Support client satisfaction initiatives (welcome calls, post-enrollment follow-ups, service recovery outreach).
Maintain quality standards, compliance expectations, and a high level of professionalism in every interaction.

Note: This role is not sales-focused and does not involve marketing, quoting, or steering clients toward plan changes.

Qualifications

Required

Strong customer service experience (phone-based preferred), with de-escalation and problem-solving skills.
Ability to work independently in a fast-paced, client-facing environment while managing multiple cases.
Comfortable using CRM systems and documenting interactions with accuracy and detail.
Reliable internet connection, dedicated workspace, and ability to handle high-volume calls/messages.

Preferred

1+ year of retention and/or client support experience in an insurance agency (Medicare experience strongly preferred).
Familiarity with common Medicare member service topics (benefits questions, carrier portals, typical service workflows).
Experience working with escalations, case management, and follow-up tracking.
Experience with CRMs/dialers/support tools (e.g., Salesforce, HubSpot, Zoho, Five9, etc.).
Bilingual (Spanish/English) a plus.

1099 Independent Contractor Classification (Important)

This role is a 1099 independent contractor position. Contractors are responsible for their own taxes and business expenses and provide their own equipment and workspace.