Medicare Retention & Sales Pro (Contract, Remote)

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

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.