Managing Director, Medicare Sales Manager

Webster Bank; Milwaukee (WI); Remote; USD 160,000 - 170,000; Full time

Job summary

Join Webster Bank as a Medicare Sales Manager and lead a team of licensed agents in a dynamic sales environment. Your role involves recruitment, coaching, and regulatory compliance while driving sales performance. Make a significant impact while benefiting from growth opportunities in a values-driven organization.

Qualifications

• Minimum 5 years of Medicare sales experience.
• 3+ years in a leadership or supervisory role.
• AHIP certification preferred.

Responsibilities

• Recruit and train licensed Medicare agents.
• Develop and implement sales strategies.
• Ensure compliance with CMS guidelines.

Skills

CMS compliance standards

Coaching

Problem-solving

Leadership

Communication

Organizational

Education

Active Life & Health License

Tools

Salesforce

Radius

AgencyBloc

Job description

Managing Director, Medicare Sales Manager page is loaded

Managing Director, Medicare Sales Manager

Apply locations WI Milwaukee time type Full time posted on Posted 3 Days Ago job requisition id R25_0000000825

If you’re looking for a meaningful career, you’ll find it here at Webster. Founded in 1935, our focus has always been to put people first--doing whatever we can to help individuals, families, businesses and our colleagues achieve their financial goals. As a leading commercial bank, we remain passionate about serving our clients and supporting our communities. Integrity, Collaboration, Accountability, Agility, Respect, Excellence are Webster’s values, these set us apart as a bank and as an employer.

Come join our team where you can expand your career potential, benefit from our robust development opportunities, and enjoy meaningful work!

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:

Team Leadership & Development

• 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.

Carrier & Product Management

• 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.

About Us

Being passionate about making a difference in people's lives is what working at Webster is all about. Since our founding in 1935, we've maintained a values-guided culture. Whether it’s helping someone buy their first home or build a business, you’ll be part of a caring team that goes above and beyond for our customers, communities and each other.

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