Medicare Retention Training Facilitator

Contract — March 2026

Fully Remote | Virtual Delivery | Contract Role

Engagement Details

• Contract role (1099 or C2C, depending on location)

• Delivery takes place across March 2026, with approximately 20 sessions

• Each session includes prep time (review and alignment), live delivery, and brief post-session follow-up

• All delivery is virtual (Zoom or Microsoft Teams)

• A producer may be provided to support the virtual classroom experience

About the Role

We are seeking experienced Medicare retention trainers and facilitators to support a large-scale, national Medicare retention enablement initiative launching in March 2026.

This program supports Medicare brokers and supervisors during the critical post-AEP period, with a strong focus on reducing voluntary disenrollment, strengthening member trust, and improving the quality of retention conversations.

This is not product training. It is a behavioral, skills-based program grounded in how seniors actually make decisions—and how effective brokers guide, support, and retain members over time.

What Makes This Program Different

• This program is built around:

• Real-world Medicare retention behaviors

• The Medicare senior decision journey

• Structured frameworks, rubrics, or cognitive progression models that help brokers:

• Understand why members want to switch plans

• Navigate uncertainty, fear, and overload

• Guide compliant, confidence-building conversations

The client is especially interested in facilitators who have previously worked with or developed retention models, such as:

1. Decision-making frameworks

2. Cognitive or behavioral progression models

3. Retention rubrics used to coach or assess broker conversations

4. Structured approaches to needs discovery, trust-building, and plan commitment

What You’ll Do

You will ideally develop and deliver a polished, repeatable one-day virtual training (2.5–3.5 hours), repeated across multiple cohorts. Your responsibilities include:

1. Leading live virtual sessions using provided facilitator guides, slides, scripts, and scenarios

2. Facilitating breakout discussions, role-plays, and applied exercises focused on:

3. Retention-focused conversations

4. Needs-based questioning

5. Trust and rapport with Medicare seniors

6. Compliance-safe decision support

7. Helping brokers confidently handle “I want to switch plans” conversations

8. Reinforcing behaviors associated with high-performing retention agents, including:

9. Active listening

10. Empathy and human connection

11. Structured follow-up

12. Consultative, non-transactional conversations

13. Reviewing all materials in advance and preparing thoroughly for each session

14. Participating in onboarding sessions and dry runs prior to live delivery

15. Ensuring a consistent, high-quality experience across all cohorts

16. Providing delivery feedback to support program refinement

You may also support a supervisor-focused version of the training, centered on coaching retention behaviors and reinforcing frameworks with broker teams.

Who We’re Looking For

We’re looking for facilitators who combine Medicare credibility, retention expertise, and strong virtual facilitation skills.

You’re a strong fit if you bring:

• 3+ years of experience in Medicare brokerage, retention, sales, member services, or related roles

• Direct experience with Medicare retention strategies (MA/MAPD, OEP/AEP experience strongly preferred)

• Prior experience facilitating or delivering Medicare-focused training (virtual or in-person)

Hands-on familiarity with:

• Retention conversations

• Disenrollment drivers

• Senior decision-making dynamics

• Experience using or referencing frameworks, rubrics, or structured models to:

• Teach retention skills

• Coach brokers or agents

• Assess conversation quality

• Comfort facilitating interactive virtual sessions (20–30+ learners), including breakout rooms and role-play

• Strong understanding of CMS-compliant communication standards

• Clear, professional communication style and a reliable virtual delivery setup

Bonus points if you:

• Have previously developed or used retention frameworks, templates, or rubrics

• Have coached or trained brokers using structured decision or behavioral models

• Can reference anonymized examples from prior Medicare retention programs

Facilitation certifications are welcome but not required.

Why Join ELB Learning

In a world where automation, robotics, and AI are transforming industries, the pressure to upskill, reskill, and future-proof your workforce has never been greater. Digital transformation isn’t just about adopting new technologies, it’s about empowering your people to grow with them. We take a consultative approach to understanding your goals, then we dig deep to design solutions that turn human capital into a strategic advantage. With ELB Learning, it’s more than a project, it’s a partnership built around your long-term growth and digital evolution.