Senior Medicare & Medicare Supplement Sales Trainer

Senior Medicare Sales Trainer – Medicare Advantage & Medicare Supplement

Location: Clearwater, FL – In Office
Job Type: Full-Time, W-2
Compensation: $65,000 per year, based on experience

About the Opportunity

We are a rapidly growing insurance organization seeking an experienced Senior Medicare Sales Trainer to lead the training, development, and ongoing coaching of our licensed Medicare and Medicare Supplement sales agents.

This is not an entry-level trainer position.

We are looking for someone with real Medicare sales experience who understands how to turn licensed agents into confident, compliant, high-performing producers.

The right candidate should understand both the technical side of Medicare and the sales side of the business. You should be equally comfortable teaching Medicare fundamentals, explaining Medicare Advantage and Medicare Supplement products, listening to live or recorded sales calls, identifying why an agent is struggling, and coaching that agent to improve.

We are looking for a trainer who can directly impact production, conversion, quality, retention, and overall agent performance.

Compensation

Base salary range: $65,000 annually.

Salary is negotiable based on Medicare industry experience, previous sales performance, training experience, leadership background, and demonstrated success developing high-performing insurance agents.

We are willing to compensate at the higher end of the range — and potentially beyond the posted range — for an exceptional candidate with extensive Medicare Advantage and Medicare Supplement experience and a proven track record of building successful sales teams.

What You'll Be Responsible For

• Lead new-hire training and onboarding for licensed Medicare agents
• Train agents on Medicare Advantage, Medicare Supplement, Prescription Drug Plans, enrollment periods, eligibility, carrier products, and Medicare fundamentals
• Develop agents' phone sales, needs-analysis, objection-handling, closing, cross-selling, and retention skills
• Conduct live call coaching, recorded call reviews, role-playing, classroom training, and one-on-one coaching
• Identify individual agent weaknesses and develop specific coaching plans to improve performance
• Work with new agents from initial training through successful transition onto the sales floor
• Provide ongoing development and advanced sales training for existing agents
• Help improve conversion rates, production, quality, placement, retention, and overall agent performance
• Develop and continuously improve training materials, scripts, presentations, testing, onboarding programs, and sales processes
• Ensure agents understand CMS requirements and maintain compliant Medicare sales practices
• Stay current on Medicare regulations, CMS changes, enrollment guidelines, carrier products, and industry developments
• Work directly with sales management and company leadership to identify performance gaps and implement solutions
• Track training effectiveness through measurable agent performance and KPI improvement
• Help create a culture centered around accountability, continuous improvement, compliance, and high performance

Who We're Looking For

We strongly prefer candidates with:

• 3 years of Medicare sales experience
• Previous experience training, coaching, leading, or managing licensed Medicare agents
• Strong knowledge of both Medicare Advantage and Medicare Supplement products
• Proven success selling Medicare products over the phone
• Strong understanding of CMS compliance and Medicare enrollment requirements
• Experience coaching agents using actual sales calls and measurable KPIs
• Experience working in a high-volume insurance sales or call-center environment
• Excellent communication, presentation, coaching, and leadership skills
• Ability to simplify complicated Medicare concepts and teach them effectively
• Ability to command a training room and keep agents engaged
• Ability to identify why an agent is struggling and provide actionable coaching rather than generic feedback
• Active Health or Life & Health Insurance License preferred
• AHIP experience/certification strongly preferred
• Experience with Medicare enrollment platforms, CRM systems, dialers, and call-center technology preferred

The Person We're Looking For

We are not looking for someone who simply reads PowerPoints, walks new hires through carrier materials, or checks boxes during onboarding.

We want someone who understands sales.

You should be able to listen to an agent's call and quickly determine why the sale was won or lost, explain what should have been done differently, demonstrate the correct approach, coach the agent through it, and then measure whether that coaching actually improved performance.

You should understand how to develop both new and experienced agents and know that every agent may require a different coaching approach.

You should also understand that successful Medicare sales training requires the right balance between production and compliance. We want knowledgeable, confident, compliant agents who can consistently perform at a high level.

What Success Looks Like

Success in this position will be measured by results — not simply by completing training classes.

We want to see:

• New agents becoming productive faster
• Increased sales conversion rates
• Improved call quality and sales skills
• Strong CMS and internal compliance
• Improved agent retention and development
• Consistent improvement among underperforming agents
• Higher overall production from the sales organization

Why Join Us?

This is an opportunity to take an important role in the continued growth of an expanding insurance organization.

You will have the ability to directly influence how our agents are trained, how our training program is structured, and how our sales organization performs.

We want someone who takes ownership of the training department and takes pride in seeing the agents they train succeed.

For the right individual, this position offers significant opportunity for professional growth, increased responsibility, and compensation growth as our organization continues to expand.

How to Apply

Please submit your resume along with a brief description of your Medicare sales and training experience.

We are particularly interested in knowing:

• How many years you have personally sold Medicare products
• How many years you have trained or managed Medicare agents
• Whether you have experience with both Medicare Advantage and Medicare Supplement
• Approximately how many agents you have trained or managed
• Examples of measurable improvements you have achieved in agent production, conversion, quality, or performance
• Your current Health/Life & Health licensing status

If you have substantial Medicare sales experience and a proven ability to develop successful agents, we would like to speak with you.

Pay: From $65,000.00 per year

Benefits:

• 401(k)
• Paid time off

Work Location: In person

Salary : $65,000