Managing Director, Medicare Sales Manager

Webster Servicing LLC; Milwaukee (WI); On-site; USD 160,000 - 170,000; Full time

Job summary

A leading company in healthcare savings is seeking a Medicare Sales Manager to lead a team of licensed agents. The role involves recruitment, managing sales strategies, and ensuring compliance with CMS regulations. Ideal candidates will have extensive Medicare sales experience and demonstrate strong leadership skills to drive performance and team culture.

Qualifications

• 5 years Medicare sales experience with 3+ years in a leadership role.
• Strong understanding of CMS compliance standards.
• Proven success in managing performance in a remote/hybrid setting.

Responsibilities

• Recruit, onboard, and train licensed Medicare agents.
• Develop and implement sales plans to meet enrollment goals.
• Ensure sales activities comply with CMS guidelines.

Skills

Leadership

Communication

Organizational

Problem-Solving

Education

Active Life & Health License

Tools

Salesforce

Radius

AgencyBloc

Job description

At HSA Bank, we’re working toward a world where everyone is empowered to save for a healthy future. Our offerings in the healthcare savings space drive down healthcare costs, increase access, and assist with decision-making for consumers, health plans, partners, and advisors.

Are you ready to join us?

Job Summary:

The Medicare Sales Manager is a driven individual that has experience hiring, leading, and growing a team of licensed Medicare agents to sell insurance products to HSA Bank and Ametros customers. The ideal candidate will have deep knowledge of Medicare Advantage (MAPD), Medicare Supplement (Medigap), and Part D Prescription Drug Plans, with a strong background in agent recruitment, coaching, and performance management. This role plays a key part in ensuring regulatory compliance, driving sales performance, and fostering a high-performance team culture.

Job Responsibilities:

Medicare Line of Business Launch Activities including:

Recruit, onboard, and train licensed Medicare agents.

Conduct regular coaching sessions and performance reviews to ensure agent success.

Monitor sales activity and agent engagement using CRM and performance tracking tools.

Sales Strategy & Execution

Develop and implement sales plans to meet monthly and annual enrollment goals.

Analyze sales metrics and adjust strategies to optimize productivity.

Partner with HSA Bank and Ametros marketing to ensure alignment on lead generation and outreach campaigns.

Compliance & Quality Assurance

Ensure all sales activities comply with CMS guidelines and internal policies.

Review recorded calls, handle complaint resolution, and monitor SOA/documentation accuracy.

Serve as the escalation point for complex client issues or compliance concerns.

Stay up-to-date on carrier plan updates and regulatory changes.

Serve as liaison between agents and carrier partners to resolve issues and disseminate information.

Facilitate product trainings and support for new plan launches.

Key skills/experience qualifications for the role:

Active Life & Health License (required).

Minimum 5 years of Medicare sales experience, with 3+ year in a leadership or supervisory role.

Strong understanding of CMS compliance standards and Medicare enrollment processes.

Proven success in coaching, managing performance, and leading a remote or hybrid team.

Proficiency with CRMs (e.g., Salesforce, Radius, AgencyBloc) and sales tracking tools.

Excellent communication, organizational, and problem-solving skills

Preferred skills/experience includes:

Experience working with FMOs or independent agent networks.

AHIP-certified and familiar with MAPD and Medigap product lines across multiple carriers.

Bilingual (Spanish or other language) a plus.

The estimated salary range for this position is $160,000USD to $170,000USD. Actual salary may vary up or down depending on job-related factors which may include knowledge, skills, experience, and location. In addition, this position is eligible for incentive compensation.

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All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or protected veteran status.