Fast Facts

Join ELB Learning as a Medicare Retention Training Facilitator for a contract role delivering key virtual training sessions focusing on member retention within the Medicare brokerage environment.

Responsibilities: Deliver virtual training sessions, guide learners through breakout activities, support retention-focused discussions, and ensure a high-quality learning experience.

Skills: Experience in Medicare brokerage, facilitating virtual training, engaging learners through interactive sessions, strong communication skills, and tech proficiency for virtual delivery.

Qualifications: At least three years of Medicare-related experience and prior experience facilitating virtual training is preferred.

Location: Fully remote position based in the USA with no travel required.

Compensation: Not provided by employer. Typical compensation ranges for this position are between $50 - $120 per hour.

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, alignment), live delivery, and brief post-work.

• All delivery is remote via Zoom or Teams.

• A producer may be provided to support the virtual classroom environment.

We’re looking for experienced Medicare trainers or facilitators to support a large-scale national retention training initiative happening in March 2026. This project will bring together hundreds of Medicare brokers and supervisors for a high-impact, virtual learning experience designed to strengthen member retention, elevate customer conversations, and improve overall plan stickiness during the critical post-AEP period.

This role is ideal for someone who understands Medicare brokerage environments, knows what strong retention behaviors look like, and feels confident facilitating structured virtual learning for adult learners.

What You’ll Do

You’ll deliver a polished one-day virtual training experience (repeated across multiple cohorts) that focuses on the skills brokers need to keep members informed, confident, and engaged. This includes:

• Leading a live 2.5–3.5 hour virtual training session using provided facilitator guides, slides, scripts, and scenarios.

• Guiding learners through breakout activities, role-plays, and practical exercises that strengthen needs-based selling, rapport building, deeper questioning, and compliance-safe communication.

• Helping brokers learn how to handle “I want to switch plans” conversations, support member decision-making, and reduce voluntary disenrollment.

• Reinforcing behaviors tied to high-performing retention agents—such as active listening, human connection, follow-up discipline, and consultative conversations.

• Reviewing all pre-built content in advance and preparing thoroughly for each session.

• Participating in onboarding sessions and dry runs before live delivery.

• Ensuring every cohort receives a consistent, high-quality learning experience.

• Offering feedback to help refine future sessions.

You may also help deliver a version of the training designed specifically for supervisors, focused on coaching and supporting their teams through retention conversations.

What Makes This Program Unique

This is not traditional Medicare plan training. It’s a behavioral, skills-focused enablement program built around what makes retention agents perform at the top of their game. You’ll be helping brokers shift from “sell at all costs” to “sell and support,” creating real value and stronger long-term member relationships.

The content will be developed by our instructional design team, with input from real top-performing retention agents. You’ll be working with a structured facilitator guide and clear talking points—no need to create content yourself, just deliver it with confidence and clarity.

What We’re Looking For

We’re searching for facilitators who bring both Medicare knowledge and engaging virtual presence—not necessarily celebrity-level performance, but someone who is credible, professional, and comfortable leading interactive sessions.

You’re a great fit if you bring:

• At least three years of experience in Medicare brokerage, sales, retention, member services, or related roles (MA/MAPD, OEP/AEP experience is very helpful).

• Prior experience facilitating virtual training for groups of 20–30+ learners.

• Comfort guiding scenario-based discussions, role-plays, and hands-on practice.

• Familiarity with CMS-compliant communication standards.

• Ability to manage engagement through breakout rooms, chats, polls, and Q&A.

• Strong communication skills and a reliable tech setup for virtual delivery.

Experience as a Medicare trainer, broker, retention specialist, sales manager, or benefits consultant is a plus. Facilitation certifications are nice to have 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.