The Opportunity

A 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 Operations

Design 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 Discipline

Establish 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 Performance

Oversee 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 Relationships

Lead 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 Team

Manage 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 for the state you reside in
• Minimum 5 years of experience in the Individual Medicare market including Medicare Advantage (MAPD) and Medicare Supplement products
• Working knowledge of CMS regulations and Medicare program requirements
• Demonstrated experience managing or overseeing teams supporting Medicare enrollment or sales operations
• Proven experience designing or improving implementation and enrollment processes
• Strong analytical, organizational, and operational problem-solving skills
• Ability to operate effectively in a cross-functional, matrixed organization

Preferred Qualifications:

• Experience working in a multi-carrier Medicare environment
• Experience with enrollment or exchange platforms such as Sunfire
• Experience with Salesforce or similar CRM systems
• Experience managing Open Enrollment readiness and agent certification programs
• Experience scaling Medicare operations across multiple states

The ideal candidate will have:

• Proven team leadership experience, managing and developing high-performing teams
• Strong operational expertise within individual health insurance products (Medicare Advantage, Supplement, PDP, and/or ACA exchange)
• In-depth knowledge of CMS regulations, compliance, and regulatory oversight
• Experience 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 execution

We’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 EST

Pay: 115,000-135,000

Location: Remote, can sit anywhere in the US

^*We will consider for employment all qualified Applicants, including those with criminal histories, in a manner consistent with the requirements of applicable federal, state, and local laws, including the City of Los Angeles' Fair Chance Initiative for Hiring Ordinance (FCIHO), Los Angeles Fair Chance Ordinance for Employers (ULAC), The San Francisco Fair Chance Ordinance (FCO), and the California Fair Chance Act (CFCA).

^*As a job position within our Insurance division, a successful completion of a background check may be required as a condition of employment. This requirement is directly related to essential job functions including but not limited to: accessing medical and confidential records, verifying financial information, and working within departments that care for vulnerable populations, such as, minors, elderly and those with physical or mental disabilities. Due to these job duties, this position has a significant impact on the business operations and reputation, as well as the safety and well-being of individuals who may be cared for as part of the job position or who may interact with staff or clients