Medicare Engagement Specialist

Cleo is the only global, holistic family care platform supporting individuals throughout every life stage.

Whether individuals are growing their family; raising babies, children, or teenagers; caring for an adult loved one; doing both as part of the growing Sandwich Generation; or taking care of their own health, Cleo provides life-changing care for families and caregivers through all stages of life. Serving more than 200 clients with members in more than 70 countries, Cleo is proven to improve mental health and decrease burnout for members, all while maximizing cost savings. Cleo delivers evidence-based interventions to improve the health & wellbeing of the family unit, decrease caregiver burnout, increase productivity, and reduce healthcare spend. Cleo has a total $84.7M investment led by top investors such as Transformation Capital, Glynn Capital, PruVen Capital, Gaingels, Greylock, NEA, and Felicis. We're a collaborative and motivated team, and now are looking for experienced and passionate team members like you to join us.

Title: Medicare Engagement Specialist

Location: Florida, Georgia, North Carolina, Tennessee, Virginia, Maryland or Texas 

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.

You’ll connect with members via phone, deliver a compelling overview of Cleo’s Medicare programming, and personalize each interaction using active listening and empathy. After enrollment, you’ll coordinate key next steps such as scheduling and administering Cleo’s health risk assessment, helping members activate their Cleo app account, and ensuring a smooth handoff to their dedicated Medicare Coach.

You’ll collaborate closely with Medicare Coaches and Medicare Operations Coordinators to provide a seamless, human-centered experience across every member touchpoint. The ideal candidate excels in clear communication, thrives in member-facing conversations, and is energized by helping people feel seen, heard, and supported as they navigate their health journey.

This role is perfect for someone who is passionate about healthcare access, member advocacy, and making a meaningful impact on the lives of older adults.