Job Details

Medicare Director

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.

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.