Call Center Sales Supervisor – Medicare & Senior Market Products

Position Summary 

Keystone Advisors is seeking a results-driven Call Center Sales Supervisor to lead, coach, and develop a team of licensed insurance agents focused on Medicare Advantage, Medicare Supplement, Prescription Drug Plans, and ancillary insurance products. This role is responsible for driving sales performance, ensuring compliance, developing future leaders, and delivering an exceptional member experience through our White Glove Service model. 

The ideal candidate possesses strong Medicare sales leadership experience, advanced technical aptitude, and a proven track record of increasing production through consultative selling, cross-selling, retention, and customer engagement strategies. This leader must be comfortable leveraging technology, CRM systems, AI-powered tools, automation, and analytics to maximize team performance and operational efficiency. 

At Keystone Advisors, we believe every member interaction is an opportunity to improve health outcomes, strengthen retention, and deliver additional value through appropriate product recommendations. Success in this role is measured not only by enrollments but by member engagement, customer lifetime value, ancillary sales performance, and overall team growth. 

Key Responsibilities 

Leadership & Team Development 

• Lead, motivate, and develop a team of licensed Medicare sales agents. 

• Conduct daily sales huddles, performance coaching sessions, and monthly development reviews. 

• Establish a culture of accountability, professionalism, and continuous improvement. 

• Identify and develop future leaders within the organization. 

• Coach agents on effective sales techniques, objection handling, compliance, and customer engagement. 

• Manage attendance, adherence, productivity, and overall team performance. 

Sales Performance & Production 

• Drive achievement of monthly, quarterly, and annual enrollment goals. 

• Monitor sales funnel performance from lead to enrollment. 

• Ensure consistent execution of outbound and inbound sales strategies. 

• Review agent performance metrics and implement corrective action plans when necessary. 

• Partner with leadership to develop campaigns that improve conversion rates and sales outcomes. 

• Support agents with escalated sales opportunities and complex member situations. 

Cross-Selling & Revenue Growth 

• Lead and coach agents on consultative selling and needs-based sales methodologies. 

• Drive cross-selling initiatives across: 

• Medicare Advantage Plans 

• Medicare Supplement Plans 

• Prescription Drug Plans 

• Dental & Vision 

• Hospital Indemnity 

• Critical Illness 

• Cancer Plans 

• Final Expense 

• Life Insurance 

• Other ancillary health and financial protection products 

• Develop strategies to increase revenue per member while maintaining compliance and customer trust. 

• Monitor ancillary attach rates and cross-sell conversion metrics. 

• Partner with Benefit Navigation and Retention teams to identify additional member opportunities. 

• Coach agents to generate referrals and strengthen long-term member relationships. 

• Utilize data analytics to identify cross-sell and retention opportunities throughout the member lifecycle. 

Technology & Digital Leadership 

• Serve as a technology champion within the sales organization. 

• Demonstrate proficiency in: 

• Salesforce CRM 

• Five9 Contact Center Platform 

• Medicare enrollment systems 

• Reporting dashboards 

• AI-powered engagement tools 

• Workflow automation platforms 

• Train and support agents in adopting new technologies and processes. 

• Partner with technology teams to improve workflows, efficiencies, and reporting capabilities. 

• Analyze performance data to drive informed business decisions. 

• Troubleshoot operational and technology-related challenges. 

Compliance & Quality Assurance 

• Ensure adherence to CMS regulations, carrier requirements, and internal policies. 

• Monitor sales calls for quality, compliance, and customer experience standards. 

• Support audit readiness initiatives and compliance reviews. 

• Reinforce HIPAA, FWA, and company compliance requirements. 

• Collaborate with Quality Assurance and Training teams to improve agent performance and reduce compliance risks. 

Reporting & Analytics 

• Analyze sales performance trends and team productivity. 

• Provide weekly and monthly reporting to leadership. 

• Monitor key performance indicators and recommend improvement strategies. 

• Forecast staffing and production needs. 

• Utilize data to improve conversion rates, retention, and member engagement. 

Cross-Functional Collaboration 

• Partner closely with: 

• Sales Leadership 

• Benefit Navigation 

• Retention Teams 

• Workforce Management 

• Quality Assurance 

• Contracting & Licensing 

• Training Department 

• Technology Teams 

• Assist with onboarding, mentoring, and training new agents. 

• Support organizational initiatives that improve member experience and operational excellence. 

Required Qualifications 

• Active Health & Life Insurance License. 

• Minimum 3 years of Medicare sales experience. 

• Minimum 2 years of call center leadership or supervisory experience. 

• Proven success leading teams in Medicare and ancillary insurance sales. 

• Demonstrated experience driving cross-selling, upselling, and retention programs. 

• Strong knowledge of: 

• Medicare Advantage 

• Medicare Supplement 

• Prescription Drug Plans 

• Ancillary Products 

• Life Insurance 

• Experience coaching agents on consultative selling and needs-based sales strategies. 

• Strong technical aptitude and ability to learn new systems quickly. 

• Advanced experience with CRM systems, sales reporting, and contact center technologies. 

• Strong communication, leadership, and problem-solving skills. 

• Ability to analyze performance data and implement action plans. 

Preferred Qualifications 

• AHIP Certification. 

• Salesforce experience. 

• Five9 experience. 

• Experience managing remote or hybrid sales teams. 

• Bilingual English/Spanish. 

• Experience utilizing AI, automation, and data analytics tools to improve sales performance. 

• Experience leading teams responsible for both new sales and retention revenue. 

Critical Success Competencies 

Leadership Excellence 

• Leads by example. 

• Creates accountability. 

• Develops future leaders. 

• Drives execution and results. 

Sales & Revenue Growth 

• Strong closer and sales coach. 

• Expert in consultative selling. 

• Skilled in cross-selling and retention strategies. 

• Focused on customer lifetime value and revenue growth. 

Technical Proficiency 

• Embraces technology and innovation. 

• Utilizes data to drive decisions. 

• Champions automation and process improvement. 

• Quickly adapts to new systems and tools. 

Member Experience 

• Customer-centric mindset. 

• Passionate about helping members navigate healthcare decisions. 

• Delivers White Glove Service. 

• Builds trust and long-term relationships. 

Performance Metrics 

Success in this role will be measured by: 

• Team Enrollment Production 

• Conversion Rate 

• Cross-Sell Conversion Rate 

• Ancillary Product Attach Rate 

• Revenue Per Member 

• Customer Lifetime Value Growth 

• Member Retention Rate 

• Referral Generation Rate 

• First Call Resolution 

• Quality Assurance Scores 

• CMS Compliance Scores 

• Attendance & Adherence 

• Customer Satisfaction Scores 

• Technology Adoption Metrics 

Keystone Advisors Core Values 

• Customer Centric 

• Integrity 

• Compassion 

• Team Player 

• Tenacious 

• White Glove Service Excellence 

Compensation & Benefits 

• Competitive Base Salary 

• Monthly Performance Bonus 

• Annual Leadership Incentive Opportunity 

• Comprehensive Benefits Package 

• Professional Development Opportunities 

• Career Advancement within the Keystone Advisors Ecosystem 

Leadership Expectation 

This role is expected to lead a high-performing sales team that delivers more than enrollments. The Call Center Sales Supervisor will drive member engagement, retention, cross-selling success, operational excellence, and technology adoption while creating a culture of accountability, ownership, and continuous improvement. This leader plays a critical role in advancing Keystone Advisors' mission of delivering exceptional member experiences and sustainable organizational growth. All while leading a team of 15+ agents while fostering a high-performance, accountable, and mission-driven culture. Provides real-time coaching and training to drive strong sales performance while maintaining a balance between conversion rates and quality compliance standards. Oversees operational performance to ensure targets are met across phone service levels, call quality, outbound contacts, and sales objectives. Manages both remote and onsite teams across multiple time zones within a fast-paced, high-growth environment. Leverages data-driven insights to support continuous improvement, enhance professional development, and sustain peak team performance across both peak and off-peak periods. Also provides escalation support by handling customer concerns with empathy and efficiency to protect the overall member experience.