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Experienced Digital Customer Service Representative – Insurance Industry

Remote, USA Full-time Posted 2026-06-16

At arenaflex, we're revolutionizing the insurance industry with our cutting-edge technology platform, empowering small businesses to easily compare and purchase the insurance they need. As a pioneer in insurance technology, we're committed to delivering exceptional customer experiences and fostering a culture of teamwork, integrity, and fun. We're now seeking a highly motivated and customer-focused Digital Customer Service Representative to join our dynamic team.

About arenaflex

arenaflex operates the largest online insurance marketplace for small businesses in the U.S., with a proprietary technology platform that enables business owners to easily compare and purchase the insurance they need. We're integrated with every major U.S. carrier, manage over $400M in premium annually, and are licensed in all 50 states. Our fast-paced team is driven by results and is energetic about servicing our clients.

Our Culture

We believe that our team members know what work location will enable them to do their best work in serving our customers. As an eCommerce workplace, we've prioritized working as virtual-first and offer access to office space in our Chicago location as a resource to work from instead of a daily workplace. We foster a service mentality inside and outside our company, and our team is passionate about delivering exceptional customer experiences.

Job Summary

We're looking for a Digital Customer Service Representative to join our firm, with the objective of obtaining the skills, proficiencies, and sustained performance to support our Digital Producers and Account Managers through retaining and servicing the arenaflex book of business. This role is viewed as a developmental position, with opportunities for growth and learning.

Key Responsibilities

• Review all bound policies for quality assurance

  • Process endorsements, certificates of insurance, and sending invoices
  • Process billing questions for new and renewal policies
  • Handle non-pay cancellation notices from Carriers to follow up for payments due
  • Post bind process and policy review
  • Identify cross sell opportunities
  • Coordinate and monitor account servicing
  • Ability to work directly with Carriers & within Carrier sites to process billing and endorsements needed for clients
  • Superior Microsoft Office experience
  • Strong organizational, customer service orientation, and disciplined time management skills
  • Comfort level with out bound dialing and phone conversations with clients
  • Insurance experience preferred
  • Ability to communicate effectively with others via the phone and email
  • Experience with multi-tasking in a fast-paced environment
  • Comfort level with working remotely

Additional or Daily Responsibilities

• Assist the Producers and AM team members to act on alerts in the agency management system

  • Act as concierge for all clients post bind, answering their billing and servicing questions
  • Proactive email sent to clients advising who their Account Manager is with all contact information
  • Facilitate the post bind process and all policy review to maintain well-documented Agency Management files, smooth customer transition from producer to account manager as well as timely policy deliverance
  • Support policy cancellation process
  • Assist with customer servicing requests from clients by working with internal teams and carrier service centers
  • Deliver excellent customer service to delight our customers in every online and offline interaction
  • Have a full understanding of the processes in our agency management system
  • Successfully be able to prioritize and support for all Producers and Account Managers
  • Coverage training and utilization of carrier trainings
  • Support client needs in a timely and well-thought-out manner
  • Develop strong communication with Underwriters

Qualifications

• Property and Casualty Licensed

  • 1-2 years of relevant insurance experience
  • Familiar with Customer Account Servicing in regulated/financial services experience preferred

Education/Experience

• High School Degree Required

  • 4 Year Degree Preferred

Computer Skills

• Word processing, spreadsheets, email software, and other related programs

  • Proficient at working with 3rd Party or Agency management systems, Various Web Applications, Client or arenaflex Agent portals, and other related online applications

Physical Demands or Requirements

This role requires sitting at a workstation for extended periods of time, while working in a dedicated office space in your home environment.

Travel Requirements

This is a virtual-first company, and no travel is required to complete the responsibilities of this assignment.

Compensation

The expected salary range for this position is $45,000-$50,000 and will be impacted by factors such as the successful candidate's skills, experience, and working location.

Why Join arenaflex?

At arenaflex, we offer a dynamic and supportive work environment, with opportunities for growth and learning. Our team is passionate about delivering exceptional customer experiences, and we're committed to fostering a culture of teamwork, integrity, and fun. If you're a motivated and customer-focused individual who is passionate about the insurance industry, we encourage you to apply for this exciting opportunity.

How to Apply

If you're ready to join a dynamic team and make a difference in the insurance industry, please submit your application, including your resume and a cover letter, to [insert contact information]. We can't wait to hear from you! Apply for this job

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