Experienced Medicare Customer Service Representative – 100% Remote Contract-to-Hire Position | Healthcare Benefits Support | Philadelphia Area

Posted 2026-05-05
Remote, USA Full-time Immediate Start
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Join Our Team as a Medicare Customer Service Representative – Transform Lives Through Compassionate Care

Are you ready to make a meaningful difference in the lives of seniors and individuals navigating their healthcare journey? arenaflex is currently seeking dedicated, empathetic, and skilled Customer Service Representatives to join our growing Medicare support team. This is a remarkable opportunity to be part of a organization that truly cares about its members and upholds the highest standards of service excellence.

As a Medicare Customer Service Representative at arenaflex, you will be at the forefront of healthcare customer care, serving as the vital connection between our members and their essential health benefits. This contract-to-hire position offers the flexibility of 100% remote work while maintaining a connection to the Philadelphia community. You will be trained to handle a variety of member inquiries, from claims questions and benefits explanations to enrollment assistance and member portal support. Your ability to listen attentively, communicate clearly, and solve problems effectively will directly impact our members' healthcare experience and peace of mind.

Why Choose arenaflex?

At arenaflex, we believe that exceptional customer service is the cornerstone of quality healthcare. We are committed to fostering an environment where every team member feels valued, supported, and empowered to deliver the five-star experience our members deserve. When you join our team, you become part of a mission-driven organization that prioritizes empathy, integrity, and excellence in everything we do.

Our culture is built on the foundation of putting people first—both our members and our employees. We understand that working in customer service, especially in the healthcare sector, requires a unique blend of skills, patience, and dedication. That's why we invest heavily in our team members through comprehensive training, ongoing support, and opportunities for professional growth. Whether you are new to the healthcare industry or bringing years of experience, arenaflex provides the resources and guidance you need to succeed.

Position Overview

We are currently recruiting for over 20 positions to support our Medicare department. This is a contract-to-hire opportunity with an initial duration of three months or more, providing you with a pathway to permanent employment based on your performance and our organizational needs. The position is fully remote, allowing you to work from the comfort of your home office anywhere within one hour of Philadelphia, Pennsylvania (19103 area). This arrangement offers unparalleled flexibility while maintaining the ability to serve our members with the dedication and personal touch they expect.

Key Responsibilities

As a Medicare Customer Service Representative at arenaflex, your primary responsibility is to deliver exceptional service to our Medicare members. Each interaction is an opportunity to make a positive impact on someone's healthcare experience. Your daily responsibilities will include:


  • Handling Inbound Member Inquiries: Professionally manage incoming calls from Medicare members seeking assistance with claims, benefits, enrollment, member portal access, ID cards, and a wide range of healthcare-related questions. You will serve as the first point of contact for members navigating their healthcare coverage.

  • Problem Resolution: Work collaboratively with members to identify issues, troubleshoot challenges, and provide effective solutions. You will use your critical thinking skills to address complex inquiries and ensure every member leaves the interaction satisfied and informed.

  • Benefits Education: Clearly explain Medicare benefits, coverage options, and enrollment procedures to help members make informed decisions about their healthcare. Your ability to translate complex information into understandable language is crucial.

  • Claims Support: Assist members with understanding their claims status, explanation of benefits, and resolving any billing discrepancies. You will navigate our systems to provide accurate and timely information.

  • Member Portal Assistance: Guide members through online registration, account access, and utilization of digital tools available through our member portal. Technology proficiency is essential for this aspect of the role.

  • Documentation and System Navigation: Accurately document all interactions in our customer relationship management systems while simultaneously navigating multiple platforms to access member information and benefits data.

  • Empathy and Tone: Maintain a warm, empathetic, and professional tone throughout every interaction. Understanding that many members may be dealing with health concerns or confusing paperwork, your compassion can make all the difference in their experience.

Work Schedule and Requirements

Our Medicare department operates seven days a week to ensure our members have access to support whenever they need it. As a full-time team member, you will work a 37.5-hour weekly schedule with flexibility to cover various shifts within our operating hours. The department is open from Sunday through Saturday, with operating hours ranging from 7:45 AM to 8:15 PM. This position requires flexibility to work:


  • One late evening shift as part of your regular schedule

  • Either a Saturday OR Sunday shift each week

  • Occasional overtime as needed, which may extend beyond 40 hours per week

Overtime is offered and sometimes required to ensure we maintain our commitment to excellent member service during peak periods. We value work-life balance and strive to create schedules that work for our team members while meeting the needs of our members.

Essential Qualifications

To succeed in this role, you must possess a combination of technical skills, interpersonal abilities, and personal attributes that enable you to deliver outstanding customer service in a healthcare setting. The following qualifications are required:


  • Customer Service Experience: Prior experience in call center customer service with a focus on inbound calls is essential. This role does not involve telesales or outbound calling—it's purely about helping and supporting members.

  • Customer-Focused Mindset: You must genuinely enjoy helping others and be committed to providing exceptional service. Service orientation and a positive attitude are non-negotiable qualities we seek in every team member.

  • Empathy and Emotional Intelligence: The ability to understand and share the feelings of others is critical. Many members may be frustrated, confused, or concerned about their healthcare. Your empathy will help calm nerves and build trust.

  • Problem-Solving Skills: You must be able to analyze situations, identify root causes, and develop effective solutions. Strong critical thinking abilities will help you navigate complex inquiries successfully.

  • Exceptional Verbal Communication: Since this is a phone-based position, you must have excellent verbal communication skills. This includes using proper grammar, professional language, and avoiding casual slang. You should be able to convey complex information clearly and effectively over the phone.

  • Written Communication: Strong written communication skills are also necessary for documenting interactions and corresponding with members via written channels when needed.

  • Multitasking and System Navigation: You must be comfortable navigating multiple computer systems simultaneously while maintaining attention to detail and accuracy.

  • Technical Assessment: All candidates must achieve a score of 80% or above on our eSkills assessment to be considered for this position.

  • Geographic Requirement: Candidates must reside within one hour of Philadelphia, PA 19103 to be eligible for this position.

Preferred Qualifications

While the following qualifications are not required, they will strengthen your application and help you excel in this role:


  • Education: High School Diploma or GED equivalent, preferably with two or more years of customer service or call center experience.

  • Healthcare Industry Experience: Previous experience in the healthcare sector, whether in insurance, provider settings, or related fields.

  • Medicare Expertise: Familiarity with Medicare programs, including Parts A, B, C, and D, as well as understanding of enrollment periods and beneficiary rights.

  • Medical Background: A background in nursing, medical assisting, or other healthcare professions can be beneficial in understanding member needs and communicating effectively about health-related topics.

  • Additional Languages: Bilingual capabilities, particularly in Spanish, are always valued and may provide additional opportunities within our diverse member population.

Compensation and Benefits

arenaflex is committed to providing competitive compensation and a comprehensive benefits package. As a full-time employee, you will have access to:


  • Competitive Pay: We offer industry-competitive hourly rates with overtime opportunities.

  • Health Benefits: Comprehensive medical, dental, and vision coverage for you and your eligible dependents.

  • Retirement Plans: 401(k) retirement savings plan with company matching contributions.

  • Paid Time Off: Generous paid time off policies including vacation, sick leave, and holidays.

  • Professional Development: Ongoing training and development opportunities to enhance your skills and advance your career.

  • Employee Assistance Program: Resources and support for personal and professional challenges.

  • Work-Life Balance: The flexibility of remote work combined with supportive management to help you thrive both professionally and personally.

Career Growth Opportunities

One of the most exciting aspects of joining arenaflex is the potential for career advancement. This contract-to-hire position is designed to transition into a permanent role for top performers. Additionally, we offer numerous pathways for growth within the organization, including:


  • Specialized roles in claims, enrollment, or quality assurance

  • Team lead and supervisory positions

  • Training and mentoring opportunities

  • Cross-functional movement into other departments

  • Continuous learning through our internal training academy

Our Commitment to Excellence

At arenaflex, we hold ourselves to the highest standards of service excellence. Our Medicare department is dedicated to providing a five-star experience to every member, every time. We believe that every interaction is an opportunity to build trust, provide value, and make a positive difference in someone's life. When you join our team, you become part of this commitment and contribute to our mission of helping individuals access the healthcare coverage they deserve with dignity and respect.

How to Apply

If you are passionate about helping others, possess the required skills and qualities, and are ready to join a team that values excellence and empathy, we encourage you to apply for this exciting opportunity. We are looking for individuals who are ready to make a meaningful impact in the lives of Medicare beneficiaries.

To be considered for this position, please submit your application online. All candidates will be required to complete the eSkills assessment as part of the evaluation process. We review applications on a rolling basis and encourage interested candidates to apply as soon as possible.

Note: All former associates and contractors must be submitted to our Vendor Management System (VMS) Program Team for vetting through the pre-submission check process before being considered for re-employment.

Join arenaflex Today

This is more than just a job—it's an opportunity to build a rewarding career while making a real difference in the lives of others. At arenaflex, you will find a supportive environment where your contributions are valued, your growth is encouraged, and your work has genuine meaning. We invite you to apply and become part of a team that is transforming healthcare customer service, one member at a time.

We look forward to welcoming you to the arenaflex family!

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