Call Center Sales Supervisor – Medicare & Senior Market Products
Houston, Texas, United States · Hybrid
$55k–$65k/yr
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Call Center Sales Supervisor – Medicare & Senior Market Products
Sign up with Clera and we'll reach out the moment a role actually fits you — no more spraying applications into the void.
$55k–$65k/yr
Full-time
Competitive Base Salary, Monthly Performance Bonus, Annual Leadership Incentive Opportunity, Comprehensive Benefits Package, Professional Development Opportunities, Career Advancement
Posted 51d ago
~40 hrs/week
Responsibilities
Lead and develop a team of licensed insurance agents to drive sales of Medicare and ancillary products while ensuring CMS compliance. Utilize technology and data analytics to optimize team performance, member retention, and revenue growth.
Requirements
Requires an active Health & Life Insurance License with at least 3 years of Medicare sales and 2 years of call center leadership experience. Must demonstrate proficiency in CRM systems and a proven track record of driving cross-selling and retention programs.
Full job description
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.
Related keywords
Medicare AdvantageMedicare SupplementPrescription Drug PlansAncillary InsuranceSalesforceFive9CMS RegulationsHIPAAFWAAHIP CertificationCRMAI-powered toolsWorkflow AutomationCustomer Lifetime ValueWhite Glove ServiceCall Center Operations
Growth partner for independent agents and agencies | BPO Services | Community-driven organization
Industry
Insurance
Company size
51-200 employees
Founded
2014
Headquarters
Houston, Texas
LinkedIn followers
2,753
Scaling in today’s healthcare landscape requires more than just access—it requires the right infrastructure, support, and partnerships.
Who We Are:
Keystone Advisors is a US-based, minority woman-owned brokerage and BPO partner specializing in Medicare and ACA markets. We sit at the intersection of healthcare operations, agent distribution, and community engagement—helping organizations grow efficiently while improving access to care.
We don’t just offer services—we become a true extension of your team.
For organizations → we bring operational scale
For agents → we provide the foundation for growth
For communities → we improve access and education
Offices: 10900 Corporate Centre Dr, 150, Houston, Texas 77041, US
MedicareAffordable Care ActLife InsuranceMarketingBPO ServicesCustomer RetentionCustomer Experienceand Back Office SupportTrainingMarketing
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