Build and Lead a High-Performance Medicare Advantage Sales Team - Remote Leadership Role with Executive Growth Potential
Are you a proven Medicare Advantage telesales leader who wants to do more than manage the status quo? Worxweb Solutions is recruiting a Medicare Advantage Telesales Manager on behalf of a fast-growing Medicare Advantage agency based in Boca Raton, FL. This is a fully remote leadership role with a strong base, production overrides, and a clear path to executive-level responsibility as the organization scales.
Position: Medicare Advantage Telesales Manager
Location: Remote - United States (Client based in Boca Raton, FL)
Hours: Monday to Friday, 9:00 AM to 6:00 PM Eastern
Job Type: W-2 Employee
Pay: $1,000 weekly base + $3 override per policy under management | Estimated $84,000 to $120,000+ annually
About Our Client
Our client is a rapidly growing Medicare Advantage telesales agency focused on inbound enrollment and building a high-performance remote sales culture. They are at an inflection point and are looking for a hands-on sales leader who wants to help build something meaningful, not just maintain an existing operation. The person who takes this role will have direct access to leadership, real influence over how the team is built and run, and a genuine opportunity to grow into an executive-level operator overseeing the entire sales organization.
Key Responsibilities
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Oversee day-to-day Medicare Advantage telesales operations for a fully remote sales team.
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Drive agent accountability, performance management, and individual production goals.
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Recruit, onboard, train, coach, and develop Medicare Advantage telesales agents.
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Coach agents on objection handling, compliance, Medicare election periods, and closing techniques.
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Monitor key performance metrics and use data to drive decisions and improve outcomes.
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Manage carrier contracting and ensure agents maintain required appointments and compliance standards.
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Collaborate with leadership to build out systems, processes, and team infrastructure as the organization scales.
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Cross-sell ancillary products including hospital indemnity, cancer, heart attack and stroke, and life insurance where applicable.
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Work a fully remote schedule with video-on leadership expectations and high accountability standards.
Requirements
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Minimum 18 months of Medicare Advantage telesales management experience required.
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Demonstrated success managing remote Medicare Advantage sales teams required.
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Proven ability to recruit, train, coach, and develop Medicare agents.
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Strong working knowledge of Medicare compliance, SEP election periods, objection handling, and sales coaching methodologies.
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Active health insurance license with the ability to obtain or maintain carrier appointments.
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Experience with the EnrollHere dialer platform and GoHighLevel CRM preferred.
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Experience cross-selling ancillary products is a plus.
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Analytical and data-driven management style with strong communication and leadership skills.
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Entrepreneurial mindset with the ability to thrive in a high-accountability remote environment.
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Long-term ambition to grow into an executive-level operator role as the organization expands.
Compensation
Base pay: $1,000 per week, W-2, guaranteed.
Override: $3 per policy under management, paid on production volume.
Estimated annual earnings:
Base production level: approximately $84,000 per year
Strong production level: approximately $100,000 per year
Top performer: approximately $120,000 or more per year
Actual earnings depend on team size, policy volume under management, and production growth.
Why This Role
Fully remote position with a structured schedule and high-accountability leadership culture. Inbound lead flow provided to the sales team. No cold prospecting required. Real opportunity to shape the culture, systems, and direction of a growing sales organization. Direct access to company leadership with the ability to influence how the team is built. Clear path to executive-level responsibility as the company continues to scale. Work alongside leadership in an environment that values ownership, initiative, and results over corporate bureaucracy. $3 per-policy override means your income grows directly as your team's production grows.
How to Apply
Submit your resume through Indeed to be considered. Qualified candidates will be contacted for a quick SMS pre-screen, so please ensure your contact details are current. All applications are handled confidentially.
