Licensed Insurance Agent

Calculated Hire; Wheeling (IL); On-site; USD 28,000 - 41,000; Full time

Job summary

Calculated Hire is seeking a Medicare Retention & Sales Specialist to support member retention and Medicare sales during the Annual Enrollment Period. This role primarily handles retention calls with current members and may handle outbound sales as volume requires. Some ANOC outreach may occur during quieter periods.

The ideal candidate balances retention and sales conversations, maintaining a compliant, professional member experience in a high-volume environment.

Qualifications

• Active license in OH and WV or able to obtain by Sep 1.
• Current AHIP certification for Medicare plan year.
• Ability to complete carrier-specific certification and appointments.
• Active National Producer Number (NPN).
• 2+ years Medicare sales/retention experience.
• Strong verbal communication and customer service skills.
• Ability to explain complex insurance information clearly.
• Comfortable in a structured, high-volume call environment.
• Reliable internet and remote workspace.
• Work Eastern Time hours for the contract.

Responsibilities

• Conduct retention calls with existing Medicare members.
• Address member concerns and prevent disenrollment.
• Handle overflow sales calls and outbound prospecting.
• Educate on Medicare Advantage and Part D options.
• Identify member needs and recommend plan options.
• Complete accurate Medicare enrollments when applicable.
• Support ANOC-related member outreach as needed.
• Maintain detailed documentation of all interactions.
• Follow CMS, state, carrier, and organizational compliance.
• Meet productivity, quality, and sales/retention targets.
• Participate in training, coaching, and team meetings.

Skills

Producer license OH/WV

AHIP certification

Carrier certification

NPN

Medicare sales/retention

Verbal communication

Customer service

De-escalation skills

Explain complex insurance

Remote work setup

Eastern Time hours

Tools

CRM

Enrollment platforms

Call center software

Job description

Contract: Contract through end of AEP season

Compensation: $25/hr

Position Overview

The Medicare Retention & Sales Specialist will support member retention and Medicare sales activity throughout the Annual Enrollment Period. This individual will primarily handle retention calls with existing Medicare members — addressing concerns, preventing disenrollment, and supporting continued member satisfaction — while also being available to handle outbound and overflow sales calls as volume requires. Some reps may also support ANOC (Annual Notice of Change) outreach during lower-volume periods.

The ideal candidate is comfortable moving fluidly between retention-focused and sales-focused conversations, and can maintain a professional, compliant member experience in a high-volume environment.

Key Responsibilities

• Conduct outbound and inbound retention calls with existing Medicare members
• Address member concerns and identify reasons for potential disenrollment
• Handle overflow sales calls and outbound prospecting as volume requires
• Educate prospective and existing members on Medicare Advantage and Part D plan options
• Identify member needs and recommend appropriate plan options within established guidelines
• Complete accurate and compliant Medicare enrollments when applicable
• Support ANOC-related member outreach as needed
• Maintain detailed documentation of all member interactions
• Follow all CMS, state, carrier, and organizational compliance requirements
• Meet established productivity, quality, and sales/retention expectations
• Participate in required training, coaching, and team meetings

Required Qualifications

• Active Accident and Health insurance producer license in Ohio and West Virginia (or must be able to obtain by September 1st)
• Current AHIP certification for the applicable Medicare plan year
• Ability to complete carrier-specific certification and appointment requirements
• Active National Producer Number
• 2+ years Medicare sales and/or retention experience (performance-based)
• Strong verbal communication, customer service, and de-escalation skills
• Ability to explain complex insurance information clearly and professionally
• Comfortable in a structured, high-volume call environment
• Reliable internet connection and appropriate remote workspace
• Ability to work Eastern Time hours throughout the contract

Preferred Qualifications

• Experience with ANOC processes
• Experience working with Medicare-eligible or senior populations
• Experience using CRM, enrollment, call center, or health insurance platforms