Experienced Customer Experience Associate – Remote Customer Support Specialist for Self-Employed Professionals (ET Hours)

Posted 2026-05-05
Remote, USA Full-time Immediate Start
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About arenaflex

The self-employed workforce represents a rapidly growing, resilient, and vibrant community of over 60 million Americans pursuing independence, flexibility, and entrepreneurial dreams. However, self-employment comes with its own unique set of challenges: navigating complex tax regulations, managing accounting and bookkeeping responsibilities, handling business banking requirements, and maintaining compliance with ever-changing financial regulations. This is where arenaflex steps in to make a meaningful difference.

arenaflex is building revolutionary tools that give self-employed individuals the security, peace of mind, and financial infrastructure that has historically only been available to employees at large corporations. We are a modern business bank account designed specifically for independent professionals, freelancers, gig workers, and small business owners. Our platform automates taxes, simplifies expense tracking, and provides intelligent financial insights because we firmly believe that small business owners should spend more time doing what they love and less time struggling with their business finances.

At arenaflex, we are looking for kind, resourceful, and passionate people to join us in building the safety net for self-employment. We are a company that values human connection, empathy, and the desire to make a positive impact on the lives of millions of independent professionals across the country. If you share our vision and want to be part of something meaningful, we would love to welcome you to our team.

About This Role

Hi, my name is Lance, and I lead the Customer Experience team here at arenaflex. The Customer Experience team is truly at the heart of everything we do. Our team directly supports arenaflex customers at every stage of their journey, from the moment they sign up and begin their onboarding experience to successfully running their businesses using our tools and resources.

Because our team is in constant, meaningful conversation with our customers, we are in a unique position to support the entire company by identifying emerging customer trends, collecting valuable product feedback, and triaging software bugs and issues. Customer Experience Associates are key to this process, enabling product and policy improvements that make arenaflex an effortless, valuable component of our customers' work lives.

We are looking for team members who are genuinely passionate about providing the best customer experience possible to the independent professionals who trust arenaflex with helping them manage their businesses. As a member of a growing team, you will also have a direct impact on how we build our team and how arenaflex builds its product. I personally review every application, so if you have any questions or want to learn more about the role, please include them in your submission.

Recent Team Accomplishments

Our Customer Experience team has been instrumental in driving positive changes throughout the organization. Some of our recent accomplishments include:


  • Launching Company-Wide Shadowing: We initiated a company-wide shadowing program that brings everyone at arenaflex closer to our customers, ensuring that every team member understands the real-world impact of their work.

  • AI Operations Integration: We have added AI operations tasks to the team's responsibilities, helping ensure that automation and AI-powered service interactions sound distinctly like arenaflex—personal, helpful, and human-centered.

  • Cross-Functional Collaboration: We regularly collaborate with product, design, and engineering teams to address frequent customer pain points, making positive changes that benefit all of our users.

What You Will Do

Day to day, you will be responsible for supporting our customers through various channels and helping maintain the high standards of service that arenaflex is known for. Your specific responsibilities will include:


  • Multi-Channel Customer Support: Support our customers via phone, chat, and email channels during arenaflex's support business hours. This role will specifically work Monday through Friday, 9am to 5pm ET. We will consider all candidates regardless of location to work within those hours, making this an ideal opportunity for those who thrive in structured schedules.

  • Knowledge Base Management: Maintain our customer-facing Help Center alongside your teammates, creating and improving articles to ensure our customers have all the information they need before contacting support. You will help build a comprehensive library of resources that empowers customers to find answers independently.

  • Voice of Customer Advocacy: Represent the Voice of Customer to our product, engineering, design, and business teams to ensure their needs are top of mind as arenaflex continues to grow and evolve. You will serve as a crucial bridge between customers and internal teams.

  • Process Improvement: Identify gaps in our internal processes on the CX team and help develop and implement improvements. Your insights will directly enhance our team's efficiency and customer satisfaction.

  • Trend Reporting: Communicate trends in customer feedback and support interactions to the rest of the company, including product, design, and engineering teams. You will help identify patterns that lead to meaningful product improvements.

To Thrive in This Role, You Should Have

We are looking for candidates who bring a combination of experience, skills, and personal attributes that will allow them to succeed in this role and grow with our team:


  • Professional Experience: 2+ years of experience providing outstanding customer support in a tech or startup environment. You should have a proven track record of delivering exceptional service and resolving complex customer issues.

  • Technical Proficiency: Experience with common customer experience platforms such as Zendesk, Salesforce, Intercom, or similar tools. Familiarity with helpdesk software, CRM systems, and communication platforms is essential.

  • Phone Skills: An aptitude for working with customers over the phone and keeping conversations productive, positive, and solution-oriented. You should be comfortable navigating challenging conversations with empathy and professionalism.

  • Remote Work Capability: Comfort working remotely and experience working with distributed teams across different time zones. You should be self-motivated, organized, and able to thrive in a work-from-home environment.

  • Communication Excellence: Excellent written and verbal communication skills, with a strong focus on empathy and problem-solving. You should be able to adapt your communication style to meet the needs of diverse customers.

  • Analytical Thinking: An interest in identifying patterns in customer conversations and bringing constructive feedback to product and/or engineering teams. You should be curious about the "why" behind customer behaviors and eager to drive improvements.

You May Also Have

While not required, the following experiences and knowledge areas would be beneficial in this role:


  • First-Hand Self-Employment Experience: Direct experience as a freelancer, gig worker, side-hustler, or any other kind of self-employment. This background provides valuable empathy and understanding of the challenges our customers face daily.

  • Financial Knowledge: A basic understanding of banking, personal finance, and/or taxes. While you don't need to be a financial expert, comfort with financial topics will help you support customers more effectively.

Compensation and Benefits at arenaflex

The anticipated salary range for this role is $30 - $33 per hour. The salary range listed represents the low and high end of the anticipated salary range for this position across all US locations. Within the range, individual pay is determined by several factors including job-related skills, experience, and relevant education or training.

Our competitive base salary is just one piece of arenaflex's total compensation package. arenaflex offers a generous and comprehensive benefits package to all employees:


  • Financial Security: 401K, FSA, and Commuter Benefits—we offer all employees access to tax-efficient benefit options alongside competitive base compensation.

  • Family Support: Paid parental leave—arenaflex supports employees through all stages of life, which is why new parents employed by arenaflex qualify for 16 weeks of flexible parental leave.

  • Health Coverage: Comprehensive medical, dental, and vision benefits. We are always 100% covered for employees and 90% covered for dependents.

  • Work Flexibility: Work anywhere—we have arenaflex offices in San Francisco and New York City. For team members who work outside those cities, arenaflex also supports fully remote working arrangements.

  • Ownership Culture: Meaningful equity—everyone on our team should feel and act like an owner, which is why arenaflex offers industry-competitive equity to all of our employees.

  • Time Off: Flexible vacation policy—vacations, appointments, mental health days—take the time you need, whenever you need to with our flexible time-off policy.

About You

arenaflex is built by a team that comes from a variety of backgrounds and experiences, and we firmly believe that diversity, equity, and inclusion are crucial to our success. We celebrate the unique perspectives and experiences each team member brings, and we know that this diversity makes us stronger as a company.

As we grow, we are searching for passionate and motivated team members who are excited to bring their skill set to the team and are ready to learn from others. We value curiosity, empathy, and the desire to make a positive impact on the lives of our customers.

If you are looking for a role where you will have the opportunity to make a meaningful contribution and great impact, we would love to hear from you! This is more than just a job—it is an opportunity to be part of a mission-driven company that is transforming the financial experience for millions of self-employed Americans.

Join Our Team

We invite you to apply for this exciting opportunity to join the arenaflex family. As a Customer Experience Associate, you will play a vital role in shaping the future of self-employment support and helping independent professionals achieve their dreams. If you are ready to make a difference, grow your career, and work with an amazing team, we encourage you to apply today.

To learn more about our benefits or the team, please visit our careers page. We look forward to potentially welcoming you to the arenaflex team!

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