Medicare Engagement Specialist - Remote

Overview

Cleo is looking for a compassionate, proactive, and relationship-driven individual to join our Medicare Member Operations team as a Medicare Engagement Specialist on a full-time, hourly basis (up to 40 hours per week during the hours of 11:30-8pm EST). In this role, you’ll serve as the first point of contact for Medicare members eligible for Cleo’s programming—introducing Cleo’s services, guiding them through enrollment, and setting the stage for long-term engagement and support.

In Short

• Proactively engage eligible members through telephonic outreach.
• Present a compelling overview of Cleo’s Medicare programming.
• Tailor conversations using active listening skills.
• Guide members through the enrollment process.
• Coordinate next steps after enrollment.
• Support members in understanding their Health Plan coverage.
• Collaborate with Medicare Operations Coordinators and Coaches.
• Maintain up-to-date records of member communications.

Requirements

• A minimum of 2-3 years in a customer-facing or sales role.
• Strong communication skills, especially over the phone.
• Comfort with telephonic outreach, including cold-calling.
• Empathy-driven mindset for engaging older adults.
• Familiarity with Medicare and health benefits navigation.
• Highly organized and detail-oriented.
• Tech-savvy with digital tools.
• Team player, eager to collaborate.
• Flexible and mission-driven.

Benefits

• Join a collaborative and motivated team.
• Impact the lives of older adults and their caregivers.
• Work in a supportive environment focused on wellbeing.