Medicare Engagement Specialist

About Cleo:

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 

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.

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.

• Proactively engage eligible members through telephonic outreach.
• Present a compelling overview of Cleo’s Medicare programming—including personalized health support, benefits navigation, and health coaching services.
• Tailor conversations using active listening skills to uncover how Cleo can support each individual’s health journey. 
• Guide members through the enrollment process by answering questions, reviewing Cleo’s terms and privacy policy, and securing verbal consent to enroll. 
• Coordinate next steps after enrollment, including scheduling and telephonically administering Cleo’s health risk assessment, introducing the Medicare Coach, and helping members activate their Cleo app account.
• Support eligible and enrolled members to better understand and access their Health Plan coverage and benefits and tailor other community resources based on member needs. 
• Collaborate efficiently with Medicare Operations Coordinators and Medicare Coaches to ensure every member interaction and transition in care is thoughtful, timely, and aligned with their unique needs.
• Maintain up-to-date records of all member communications, enrollment steps, caregiver involvement, and next actions in Cleo’s internal systems.

• A minimum of 2-3 years in a customer-facing or sales role, ideally within healthcare, insurance, or social services. Experience in outreach, member engagement, or customer support is strongly preferred.
• Strong communication skills, especially over the phone, with the ability to explain services clearly, build rapport quickly, and adapt tone to meet individual needs.
• Comfort with telephonic outreach, including cold-calling, and confidence in initiating conversations with new members.
• Empathy-driven mindset, with proven ability to engage older adults and their family members or caregivers with varying health literacy levels.
• Familiarity with Medicare and/or health benefits navigation is a strong plus.
• Highly organized and detail-oriented, with the ability to track member interactions and follow-up steps accurately in internal systems.
• Tech-savvy, with comfort using digital tools such as CRMs, scheduling platforms, and communication systems (e.g., Slack, Zoom, email).
• Team player, eager to collaborate with colleagues across care, coaching, and operations to deliver a seamless member experience.
• Flexible and mission-driven, with a desire to improve access to care and support the well-being of aging adults and their caregivers.

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We don’t believe in perfection – we believe in passion, interest, and will – so don’t let a lack of experience or skill in one area listed above deter you from applying.

Cleo is proud to be an Equal Opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.

Pay Transparency: The base rate for this position is $23-27 per hour for 35-40 hours per week. Additional benefits include health insurance (medical, dental, and vision), 15 paid holidays, 5-day winter break, accrued vacation time, sick time, 16 weeks paid parental leave, 401(k) plan, disability insurance, life insurance, wellness perks, and more.

You must be based in the U.S. and authorized to work in the U.S. without employer sponsorship. Please be advised that Cleo does not provide employment-based visa sponsorship for this position at this time.

Cleo is currently accepting applications from candidates for this role residing in the following states: Florida, Georgia, North Carolina, Tennessee, Virginia, Maryland, or Texas.

SF FAIR CHANCE ORDINANCE Pursuant to the San Francisco Fair Chance Ordinance, Los Angeles Fair Chance Initiative for Hiring Ordinance, and any other state or local hiring regulations, we will consider for employment any qualified applicant, including those with arrest and conviction records, in a manner consistent with the applicable regulation.