Medicare Enrollment Specialist (Remote)

We are seeking Fully Remote Medicare Enrollment Specialists to join a growing healthcare organization supporting Medicare beneficiaries through the enrollment process. This is a non-sales, consultative role focused on providing personalized education and helping individuals understand their Medicare options.

Enrollment Specialists will conduct one-on-one virtual meetings via Microsoft Teams, appearing on camera while educating beneficiaries about available Medicare plans and benefits. This is an excellent opportunity for a personable, detail-oriented professional who enjoys helping others and is comfortable working in a highly visible virtual environment.

Key Responsibilities

• Conduct one-on-one virtual Medicare enrollment education meetings via Microsoft Teams.
• Explain Medicare options, plan benefits, and coverage details in a clear, easy-to-understand manner.
• Review and interpret Summary of Benefits documents to accurately educate beneficiaries.
• Provide objective, consultative guidance without sales quotas or commissions.
• Document member interactions and enrollment discussions accurately in HubSpot.
• Upload meeting recordings and required documentation to SharePoint.
• Maintain strict attention to detail and ensure accurate, compliant documentation.
• Participate in training, coaching, and ongoing professional development.
• Deliver a professional and engaging experience while working on camera with beneficiaries and client employees.

Required Qualifications

• Active professional license in any U.S. state.
• Previous experience working with Medicare.
• Ability to read, understand, and explain Summary of Benefits documents.
• Strong communication and interpersonal skills.
• Comfortable conducting meetings on camera via Microsoft Teams.
• Strong attention to detail and documentation skills.
• Professional, personable, and socially confident virtual presence.
• Ability to receive feedback and demonstrate a willingness to learn and improve.

Preferred Qualifications

• Experience with Medicare Supplements.
• Previous Medicare sales or enrollment experience.
• Familiarity with HubSpot or similar CRM platforms.
• Experience working with virtual healthcare or enrollment platforms.

Schedule

Initial Training & Pre-Open Enrollment:

• Monday-Friday, 8:00 AM-5:00 PM

National Open Enrollment Period:

• Coverage window spans 7:00 AM ET-7:00 PM PT.
• 10-hour workdays are required during this period.
• Overtime opportunities are available.
• Rotating Saturday and Sunday shifts will be required.

What We're Looking For

Because this role involves spending significant time on camera, the ideal candidate is:

• Highly personable and comfortable engaging with people virtually.
• Socially aware with strong communication skills.
• Coachable and receptive to feedback.
• Detail-oriented and committed to accuracy.
• Professional while maintaining a positive "work hard, play hard" attitude.
• Comfortable working independently in a remote environment.
• Equipped with a professional work-from-home environment and reliable high-speed internet.

Career Growth & Benefits

• Non-sales, consultative environment - no commission-based sales expectations.
• Significant opportunities for career advancement and upward mobility.
• Join a rapidly growing organization experiencing approximately year-over-year growth.
• Supportive leadership and collaborative team environment.
• Opportunity to play a key role in helping 1,500-2,000 Medicare beneficiaries navigate their enrollment options.
• Client-provided work equipment.

Compliance & Onboarding

• Background check required.
• Professional license verification required.
• Candidates should be prepared to provide a copy of their active license during the interview process.
• Start date is approximately one week following successful clearance.

This is a great opportunity for a licensed healthcare professional with Medicare experience who enjoys patient education, connecting with people, and building a long-term career in a growing organization.

For California Applicants:

We will consider for employment all qualified Applicants, including those with criminal histories, in a manner consistent with the requirements of applicable federal, state and local laws, including the City of Los Angeles' Fair Chance Initiative for Hiring Ordinance (FCIHO), Los Angeles Fair Chance Ordinance for Employers (ULAC), The San Francisco Fair Chance Ordinance (FCO) , and the California Fair Chance Act (CFCA).

This position is subject to a background check based on its job duties, which may include patient care, working with vulnerable populations, access to financial and confidential information, driving, working with heavy machinery, or working in a warehouse or laboratory environment. Due to these job duties, this position has a significant impact on the business operations and reputation, as well as the safety and well-being of individuals who may be cared for as part of the job position or who may interact with staff or clients.