Experienced Remote Health & Benefits Customer Service Specialist – Supporting FSA, HSA, COBRA & Healthcare Reimbursement Accounts

About arenaflex

At arenaflex, we are transforming the way individuals and businesses navigate their health and wealth journeys. As a leader in the employee benefits and financial wellness industry, we provide innovative solutions that help millions of people plan, save, and invest for a brighter future. Our mission is to deliver exceptional service and simplify the complex world of healthcare reimbursement accounts, flexible spending accounts, and retirement planning.

We believe that great companies are built by great people, and we are committed to fostering an environment where talent thrives, diversity is celebrated, and every team member has the opportunity to grow. Join us and become part of a community that values integrity, collaboration, and an unwavering dedication to our clients' success.

Position Overview

Are you passionate about helping others navigate their healthcare benefits? Do you thrive in fast-paced environments where every interaction matters? We are looking for a dedicated Health & Benefits Customer Service Representative to join our dynamic team. In this role, you will be the frontline ambassador for arenaflex, partnering closely with accountholders who call our contact center seeking guidance, education, and support on their healthcare reimbursement accounts.

This position offers the unique opportunity to work remotely from the comfort of your home while making a meaningful impact on people's financial wellness. You will be instrumental in helping individuals understand and maximize their Flexible Spending Accounts (FSA), Health Savings Accounts (HSA), COBRA coverage, and other valuable benefit programs. If you are someone who enjoys problem-solving, possesses excellent communication skills, and takes pride in delivering exceptional customer experiences, this role is perfect for you.

Key Responsibilities

As an H&B Support Specialist at arenaflex, you will play a critical role in ensuring our accountholders receive the highest level of service. Your daily responsibilities will include:

• Accountholder Support: Respond to incoming calls from members seeking assistance with their healthcare reimbursement accounts. Provide friendly, empathetic, and knowledgeable support to ensure every caller feels valued and understood.
• Product Education: Explain how FSA, HSA, COBRA, and other benefit programs work. Help accountholders understand their plan details, coverage options, eligibility requirements, and how to maximize their benefits.
• Account Assistance: Guide accountholders through our online tools and mobile applications. Assist with actions such as checking account balances, submitting claims, reviewing transaction histories, and updating personal information.
• Issue Resolution: Take ownership of member concerns and work diligently to resolve issues without escalation to management. Employ strong problem-solving skills to remove barriers and ensure satisfactory outcomes.
• Compliance & Quality Assurance: Maintain thorough knowledge of all internal quality assurance standards, technical policies, and regulatory requirements. Ensure every interaction adheres to compliance rules and protects sensitive member information.
• Multi-Channel Support: After completing initial training, you may receive additional call type skills and be cross-trained to support other communication channels such as chat, email, or text messaging based on business needs.
• Documentation & Accuracy: Maintain detailed and accurate records of all customer interactions using our digital workflow systems. Ensure proper documentation for quality assurance and regulatory compliance.
• Performance Excellence: Meet or exceed member service goals and deadlines while handling a high volume of calls in a fast-paced environment. Prioritize tasks effectively to maintain productivity and quality standards.

Essential Qualifications

To succeed in this role, you must meet the following requirements:

• Experience: Minimum of 2 years in customer service roles and 2 years of call center experience is required.
• Technical Skills: Proficient computer skills with the ability to learn and navigate new systems quickly. Comfortable using digital workflows and multiple software platforms simultaneously.
• Communication: Excellent oral and written communication skills with the ability to convey complex information clearly and professionally.
• Problem-Solving: Strong analytical and problem-solving abilities to address member concerns effectively and independently.
• Work Ethic: Ability to work in a fast-paced environment, managing up to 50 calls per day while maintaining high-quality standards.
• Attention to Detail: Strong attention to detail and accuracy in documentation and data entry.
• Empathy & Patience: Genuine ability to connect with accountholders on a human level, demonstrating empathy, understanding, and respect in every interaction.
• De-escalation Skills: Capability to de-escalate tense situations and handle member issues without supervisor intervention.
• Availability: Must be available to work Monday through Friday, 12:30 PM – 9:00 PM CT, with one weekday off (e.g., Wednesday). Additionally, must work Saturdays, 10:30 AM – 7:00 PM CT. Must be able to work overtime as required by business needs.

Physical Requirements: Prolonged periods of sitting at a desk and working on a computer. Occasionally lift items up to 25 pounds.

Preferred Qualifications

While not required, the following qualifications will help you excel in this role:

• Basic understanding of medical and healthcare reimbursement terminology


• Previous experience in the health insurance or benefits administration industry


• Familiarity with FSA, HSA, and COBRA programs


• Experience with multi-channel customer service (chat, email, text)


• Knowledge of compliance regulations related to healthcare accounts

Technical Requirements

As this is a remote position, you must have a quiet, distraction-free work environment without any conflicting responsibilities during your scheduled shift. Additionally, you must meet the following internet speed requirements:

• Upload Speed: Greater than 20 Mbps


• Download Speed: Greater than 100 Mbps


• Must be able to hardwire an ethernet cable directly to your internet modem/router for reliable connectivity

Training & Development

We are invested in your success! All new team members will participate in a comprehensive training program designed to equip you with the knowledge and skills needed to excel in this role.

• Training Start Date: Monday, October 20, 2025 (subject to change based on business needs)


• Training Duration: Approximately 4-5 weeks


• Training Schedule: 7:00 AM ET to 3:30 PM CT


• Training Pay: Training is paid, and you will accrue PTO during this period


• Certification Requirement: A passing score of 85% is required on the product exam at the end of training to continue in this position

Important Note: Attendance is mandatory during the entire training period. While PTO accrues during training, PTO cannot be taken during the training period.

What We Offer

At arenaflex, we believe in rewarding our team members for their hard work and dedication. Our comprehensive benefits package includes:

• Competitive Compensation: Starting rate of $18.50 per hour


• Incentive Opportunities: Performance-based bonuses and incentive programs


• Health & Wellness: Comprehensive healthcare coverage including medical, dental, and vision plans


• Financial Security: 401(k) savings plan with company contributions


• Paid Time Off: Generous PTO policy including holidays, personal days, and vacation


• Parental Leave: Paid leave for new parents


• Employee Assistance Program: Confidential support services for personal and professional challenges


• Career Development: Opportunities for advancement and professional growth within the organization

Equipment Provision

We provide all necessary equipment to ensure you have everything you need to succeed in your remote role:

• Laptop (x1)


• Monitor (x2)


• Docking Station (x1)


• Keyboard (x1)


• Mouse (x1)


• Headset (x1)

Work Environment & Culture

At arenaflex, we pride ourselves on fostering a collaborative, inclusive, and supportive work environment. We believe that when our team members thrive, our clients thrive. Here's what you can expect:

• Remote Flexibility: Work from home with the autonomy to create your ideal workspace


• Inclusive Culture: We value diversity and believe there is no "perfect" candidate. We encourage applications from all backgrounds and experiences


• Team Collaboration: Join a team of forward-thinking individuals who are passionate about helping others


• Growth Mindset: Continuous learning opportunities and pathways for career advancement


• Recognition: We celebrate achievements and reward outstanding performance

We have been recognized for our remarkable growth and outstanding workplace culture. Join a company that has been featured on prestigious lists such as Crain's Fast 50 and Inc. 5000, and awarded for our workplace excellence.

Join Our Team

If you are ready to take the next step in your career and make a meaningful impact in the lives of others, we encourage you to apply today! At arenaflex, you will help businesses and individuals thrive today, tomorrow, and into retirement.

Become part of a company that is people-centric and client-obsessed in every interaction—a community of forward-thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. We are always looking to expand our growing team with dynamic and enthusiastic individuals who are eager to learn and grow.

If you enjoy a collaborative, supportive environment that champions career development, arenaflex is the place for you! We look forward to receiving your application and learning more about how you can contribute to our mission.

Ready to apply? Take the next step in your journey with arenaflex today!