Medicare Director

Insurance Lounge Job Description- Medicare Director

Role Overview

The Medicare Director is responsible for the overall success of all Medicare-related products, including Medicare Advantage, Medicare Supplement, and Prescription Drug Plans. This role drives production, ensures strict compliance with CMS regulations, manages carrier relationships, and maintains deep product expertise across the organization. The Product Director owns seasonal planning (AEP/OEP), ensures team readiness, and maintains full visibility into the health, compliance, and performance of the Medicare book of business. This role regularly presents strategic plans, adjustments, and pivots to meet growth, retention, and compliance standards.

Why Join Insurance Lounge?

This role represents a unique opportunity to take ownership of an established but growing Medicare division within a forward-thinking, independent agency. Insurance Lounge values leadership, accountability, compliance, and innovation, and empowers its directors to shape Medicare strategy, lead high-performing teams, and drive meaningful growth across all Medicare product lines. The Medicare Director will play a critical role in seasonal success, including AEP and OEP execution, while maintaining strict adherence to CMS guidelines and delivering an exceptional client experience.

This position offers a seat at the table with executive leadership and the ability to directly influence Medicare growth, compliance standards, and long-term organizational strategy. For a proven Medicare leader seeking long-term impact, professional autonomy, and the opportunity to build and scale a best-in-class Medicare program, this role offers both challenge and reward.

Primary Objectives

Own production through personal & department growth, and retention for all Medicare product lines (MAPD, PDP, Med Supp)

Ensure full compliance with CMS guidelines across self and all team members

Manage and strengthen Medicare carrier relationships 

Serve as the internal Medicare product expert, including plan knowledge, compliance, and positioning

Oversee and enforce compliant sales practices, including Scope of Appointment (SOA), documentation, and marketing guidelines

Track and maximize carrier incentives, bonus programs, and production tiers

Maintain a clear, real-time understanding of Medicare book performance and compliance status

Lead all Medicare seasonal planning, including AEP and OEP strategy, staffing, and execution

Identify gaps in production, compliance, or process and present actionable solutions

Lead and coordinate Medicare product and compliance training for sales and support teams

Partner with leadership to align Medicare strategy with overall company growth goals

Provide consistent reporting on production, retention, compliance adherence, and trends

Identify new carrier opportunities and market expansion strategies within Medicare

Oversee client experience and issue resolution specific to Medicare policies.

Key Performance Indicators (KPIs)

Medicare policy retention rate

Active Medicare client count

Total Medicare policy count (by product type)

AEP production results vs. targets

OEP production and retention performance

Compliance audit results (internal and external)

SOA and documentation accuracy rates

Carrier bonus and incentive performance vs. targets

Medicare training and compliance sessions completed

Leadership reporting cadence (monthly/quarterly)

Success Looks Like

Lead by example through personal production to demonstrate product knowledge

Medicare book of business is growing, retained, and compliant

AEP and OEP are executed with strong production and zero compliance issues

Team demonstrates confidence and accuracy in Medicare product knowledge and compliance

Carrier partnerships are strong, engaged, and producing results

Leadership has clear visibility into Medicare performance and risk areas

Compliance issues are proactively prevented, not reactively corrected

Required Qualifications

8+ years of Medicare insurance experience with direct responsibility for selling, servicing, and managing Medicare Advantage, Prescription Drug Plans, and Medicare Supplement products
• 8+ years of experience building, leading, and managing a Medicare sales and/or service team
• Demonstrated experience developing Medicare growth strategies, including AEP/OEP planning, and presenting recommendations to executive leadership
• Proven success establishing and managing Medicare carrier relationships and identifying market expansion opportunities
• Strong technical knowledge of Medicare products, CMS regulations, compliance requirements, and enrollment processes
• Hands-on experience ensuring compliant sales practices, including Scope of Appointment (SOA), documentation, and marketing guidelines
• Extensive experience with Applied Epic or a comparable CRM/agency management system, including Medicare tracking and reporting
• Proven ability to lead teams, drive accountability, and deliver measurable production, retention, and compliance results

Work Location & Compensation

This is a full-time, in-person leadership role based out of Insurance Lounge’s corporate headquarters in Grants Pass, Oregon. Competitive director-level compensation is offered, including base salary, performance-based bonus opportunities tied to Medicare production, retention, and compliance performance, with negotiable relocation and signing bonuses for qualified candidates.