Job Description

About All Insurance Advisors

All Insurance Advisors (AIA) is a growing Medicare-focused insurance agency dedicated to helping beneficiaries make informed healthcare decisions.

We combine modern technology, a steady flow of inbound consumer inquiries, and hands-on agent support to build a high-performing Medicare sales organization.

As we continue expanding, we're looking for an experienced Medicare Sales Trainer who knows what it takes to succeed on the phones and can teach others to do the same.

About the Role

We're looking for someone who has been a top-performing Medicare sales agent and is ready to help develop the next generation of successful agents.

The ideal candidate has a proven track record of strong Medicare sales conversion, excellent compliance practices, and the ability to coach agents to improve their performance.

You'll work directly with licensed agents, listening to calls, identifying opportunities for improvement, conducting training sessions, and helping agents strengthen their sales conversations.

This is a hands-on position. We're not looking for someone who simply delivers presentations or teaches Medicare fundamentals. We want someone who understands the realities of selling Medicare over the phone and can translate that experience into measurable improvements in agent performance.

Your mission: Help our agents become more confident, effective, and compliant Medicare sales professionals.

Key Responsibilities

Sales Coaching & Performance Improvement

• Coach Medicare agents to improve call conversion rates, enrollment performance, and overall sales effectiveness.
• Review recorded and live sales calls to identify strengths, weaknesses, and coaching opportunities.
• Teach agents how to conduct effective needs analyses, communicate plan value, and confidently guide beneficiaries through enrollment decisions.
• Help agents improve objection handling, build trust, and navigate difficult customer conversations.
• Develop individualized coaching plans for agents who need additional support.
• Work with sales leadership to identify performance trends and opportunities for improvement.

Agent Training & Development

• Conduct engaging individual and group training sessions focused on real-world Medicare sales situations.
• Help newly hired agents transition from initial training to successful live sales conversations.
• Lead role-playing exercises, mock calls, and practical sales workshops.
• Reinforce effective call structure, discovery techniques, product presentation, and enrollment processes.
• Share proven sales techniques and best practices that help agents improve their performance.
• Develop coaching materials and training resources based on actual sales floor challenges.

Compliance-Focused Sales Excellence

• Reinforce compliant Medicare sales practices while helping agents achieve strong conversion rates.
• Coach agents on CMS marketing and enrollment requirements, appropriate plan presentations, and accurate beneficiary communications.
• Identify potential compliance concerns during call reviews and coordinate with compliance leadership when necessary.
• Teach agents how to conduct thorough needs analyses and recommend suitable coverage options without using misleading or high-pressure tactics.
• Promote a sales culture where compliance, customer experience, and performance work together.

Real-Time Sales Floor Support

• Provide hands-on guidance when agents encounter difficult sales conversations or challenging Medicare scenarios.
• Help agents navigate common eligibility, plan comparison, and enrollment questions.
• Collaborate with sales managers and product specialists to address recurring challenges.
• Identify coaching opportunities that can be addressed through additional training or process improvements.

Qualifications

Required:

• 3+ years of successful Medicare sales experience, with significant hands-on experience selling Medicare Advantage plans.
• Demonstrated history of strong sales conversion rates and consistent enrollment performance.
• Strong understanding of Medicare sales processes, customer needs analysis, and objection handling.
• Excellent knowledge of CMS Medicare marketing, sales, and enrollment compliance requirements.
• Ability to evaluate sales calls and provide clear, actionable coaching feedback.
• Strong communication, teaching, and leadership skills.
• Active health insurance producer license.

Preferred:

• Previous experience as a Medicare sales trainer, sales coach, team lead, or high-performing senior agent.
• Proven success improving other agents' sales conversion rates.
• Experience training agents in an inbound Medicare sales environment.
• Familiarity with Medicare Advantage, MAPD, D-SNP, C-SNP, and PDP products.
• Experience with SunFire, call monitoring systems, CRM platforms, and Medicare enrollment tools.
• Experience developing structured agent training programs, role-playing exercises, and performance improvement plans.

What Success Looks Like

• Agents demonstrate measurable improvements in sales conversion rates and enrollment performance.
• New agents become productive more quickly and develop strong sales habits.
• Underperforming agents improve through targeted, actionable coaching.
• Agent confidence, product knowledge, and communication skills continuously improve.
• Compliance standards remain consistently high as sales performance increases.
• The sales team develops a repeatable, effective, and beneficiary-focused sales process.

Why Join All Insurance Advisors?

At AIA, we're building a growing Medicare sales organization that invests in its agents, technology, and long-term development.

You'll have the opportunity to work closely with sales leadership, directly influence agent performance, and help shape the training and coaching programs that support our continued growth.

We're looking for someone who takes pride not only in their own sales achievements, but also in helping others become exceptional Medicare agents.

If you've been a top-performing Medicare agent, know how to convert calls while maintaining excellent compliance, and love helping others succeed, we'd love to hear from you.

Apply today to join All Insurance Advisors.

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