Health Plan Advisor

The Judge Group
The Judge Group

Remote

Posted on Jul 21, 2026

Health & Life Insurance Retention Specialist (Remote)

Job Details

  • Job Title: Retention Specialist / Re-Sales Representative – Individual Medical Plans

  • Work Arrangement: 100% Virtual / Remote (Must have a private, quiet workspace)

  • Work Schedule: Monday – Friday, shifts between 8:30 AM – 9:00 PM EST (Based on business needs; candidates must be flexible to work any shift. Possibility of weekends and OT).

  • Training Schedule: 7:30 AM PST – 4:00 PM PST (Coordinated per time zone). Note: No time off requests will be accepted during training.

  • Location: Open to candidates from all states.

  • Patient/Member-Facing: No (Telephonic/Written outreach only).

Job Description

The Retention Specialist is responsible for re-selling Individual Medical Plans to existing members across all operating states. This role focuses heavily on increasing member retention and decreasing lapse rates by proactively consulting with at-risk members.

Key Responsibilities

  • Provide detailed analysis identifying and promoting the value of the member's existing health plan.

  • Counsel members on alternative plan options and make recommendations to align with their needs and budget.

  • Proactively engage with members during rate increases, cancellation requests, or other periods where a member is at risk of leaving to prevent attrition.

  • Partner with the Underwriting team to facilitate enrollment into alternate plan options when a selected plan becomes unavailable due to rate-ups or structural changes.

  • Follow up on warm retention leads via outbound calls and formal written communications.

Position Requirements & Qualifications

Required Education & Experience

  • Education: BA/BS degree OR an equivalent combination of education and experience.

  • Experience: 3–4 years of Life & Health insurance experience within sales and/or member services.

Required Licenses & Technical Setup

  • Licensure: Must hold a currently active Resident Health & Life Insurance License in at least one state. Must be willing and eligible to be licensed in all required states (the business will pay conversion/non-resident fees).

  • Internet Infrastructure: High-speed internet with a minimum of 100 Mbps download speed.

  • Connection Requirement: Wi-Fi is strictly prohibited. Must be able to connect via a hardwired short Ethernet cable directly into the router.

Preferred Skill Sets

  • Proven background in Insurance Sales, Customer Service, or High-Volume Call Centers.

  • Strong multi-tasking abilities with advanced IT skills (navigating multiple monitors and fast-paced systems simultaneously).

  • Proficiency with Windows 11 and Microsoft Office Suite.

By providing your phone number, you consent to: (1) receive automated text messages and calls from the Judge Group, Inc. and its affiliates (collectively “Judge”) to such phone number regarding job opportunities, your job application, and for other related purposes. Message & data rates apply and message frequency may vary. Consistent with Judge's Privacy Policy, information obtained from your consent will not be shared with third parties for marketing/promotional purposes. Reply STOP to opt out of receiving telephone calls and text messages from Judge and HELP for help.

Apply now