Medicare Program Director - 251808

The OpportunityA growing national Individual Medicare program that helps retirees navigate Medicare coverage options with personalized guidance and advocacy.As the program continues to expand, we are seeking an Individual Medicare Program Director to help strengthen and scale the operational framework supporting this business.In this role, you will help advance the structure and discipline that supports our Individual Medicare offering, including implementation processes, enrollment workflows, and Open Enrollment readiness. You will work closely with leadership across Sales, Advocacy, Compliance, and carrier partners to ensure the program continues to scale efficiently while maintaining a high-quality experience for retirees.This is a player-coach leadership role combining hands-on operational leadership with oversight of a small team. Candidates who have successfully led operational execution through Medicare Open Enrollment cycles and enrollment implementation will be particularly well suited for this role.What You Will Do:Build and Scale OperationsDesign and formalize the operational framework supporting our Individual Medicare program, including enrollment workflows, implementation timelines, and service processes.Develop structured implementation plans for Medicare Advantage Prescription Drug (MAPD) and Medicare Supplement offerings, ensuring operational readiness for Open Enrollment and ongoing growth.Create scalable processes supporting enrollment operations, carrier coordination, case management, and member advocacy.Ensure Operational DisciplineEstablish operational checkpoints within implementation timelines to ensure consistent execution and service quality.Oversee agent licensing and certification tracking to maintain uninterrupted selling capability.Identify operational risks and implement safeguards that support stable program growth.Drive Enrollment PerformanceOversee end-to-end enrollment execution and operational quality.Monitor key performance metrics including enrollment cycle time, error rates, and escalation trends.Partner with Advocacy leadership to support licensed Medicare agents and ensure operational alignment across the enrollment lifecycle.Manage Carrier and Platform RelationshipsLead operational relationships with national and regional Medicare carriers.Oversee carrier onboarding, annual product refresh cycles, and configuration updates.Serve as an escalation point for carrier or platform issues impacting enrollment or member experience.Drive improvements to enrollment and exchange platforms to enhance efficiency and accuracy.Lead and Develop the TeamManage a small operational team while serving as a hands-on contributor.Drive workforce planning, capacity management, and operational reporting.Influence cross-functional partners across Sales, Advocacy, Compliance, and Executive leadership to ensure aligned execution.Required Qualifications:Active health insurance license required at the time of hire for the state you reside inMinimum 5 years of experience in the Individual Medicare market including Medicare Advantage (MAPD) and Medicare Supplement productsWorking knowledge of CMS regulations and Medicare program requirementsDemonstrated experience managing or overseeing teams supporting Medicare enrollment or sales operationsProven experience designing or improving implementation and enrollment processesStrong analytical, organizational, and operational problem-solving skillsAbility to operate effectively in a cross-functional, matrixed organizationPreferred Qualifications:Experience working in a multi-carrier Medicare environmentExperience with enrollment or exchange platforms such as SunfireExperience with Salesforce or similar CRM systemsExperience managing Open Enrollment readiness and agent certification programsExperience scaling Medicare operations across multiple statesThe ideal candidate will have:Proven team leadership experience, managing and developing high-performing teamsStrong operational expertise within individual health insurance products (Medicare Advantage, Supplement, PDP, and/or ACA exchange)In-depth knowledge of CMS regulations, compliance, and regulatory oversightExperience working in or alongside organizations such as FMOs (Field Marketing Organizations), broker/agency channels, or health plan environments (e.g., carriers, benefits administrators)Ability to bridge product strategy and day-to-day operations, ensuring compliant and effective product executionWe’re looking for someone who understands the full lifecycle of individual products—from strategy through implementation—while navigating the complexities of Medicare and regulatory requirements.Hours: Monday-Friday, flexibility with hours - most likely ~9am-5pm ESTPay: 115,000-135,000Location: Remote, can sit anywhere in the US