Experienced Customer Service Representative III – Outbound Member Engagement & Association Support (Remote with Quarterly Chicago Onsite)

About arenaflex

arenaflex is a forward-thinking organization that partners with leading professional associations to elevate member experiences and drive meaningful engagement. In collaboration with a respected medical association, arenaflex is building a dedicated customer service team that combines the warmth of personalized support with the precision of sales-driven outreach. If you are a customer service professional who thrives in a high-volume, phone-based environment and is motivated by helping members unlock the full value of their association benefits, this opportunity at arenaflex is designed for you.

This is a temp-to-perm, remote role with a structured Monday through Friday schedule (8:30am to 5:00pm CST) and a quarterly onsite presence in our Chicago office 6 to 8 times per year for special events, team gatherings, and strategic planning sessions. The compensation begins at $22 to $23 per hour, with a projected annual salary of $45,000 to $48,000 upon conversion to a permanent position with arenaflex.

Position Overview

As a Customer Service Representative III at arenaflex, you will serve as a trusted point of contact for members of a nationally respected medical association. Your primary mission is to deliver an exceptional service experience on every interaction while actively contributing to the organization’s growth through outbound engagement, upselling, and cross-service initiatives. Roughly 60% to 70% of your week will focus on outbound calling, giving you the opportunity to proactively reach members, introduce them to new benefits, and ensure they are maximizing the value of their membership.

This role is ideal for a polished, articulate, and sales-minded customer service professional who can balance empathy and persuasion in equal measure. You will not only answer questions about membership, products, and subscriptions, you will also champion service improvement projects, contribute to team performance goals, and act as a knowledgeable ambassador for the association.

Key Responsibilities

• Proactively conduct outbound calls to members, prospects, and customers as part of structured sales and up-service programs designed to meet specific unit goals. This outbound work represents 60% to 70% of weekly activity.
• Handle inbound and outbound phone inquiries of all types regarding membership benefits, membership pricing, account status, and general service questions in an efficient, professional, and courteous manner.
• Support members in accessing and navigating the association website by assisting with registration, account setup, password resets, and general technical navigation questions.
• Respond to service inquiries about association products by providing detailed information on product features, pricing, order status, and billing inquiries.
• Manage inquiries related to print and online journal subscriptions, including product information, pricing, order entry, order status, billing research, and resolution of service interruptions. Send back issues or make appropriate subscription adjustments as required.
• Enter and process journal orders accurately in the association’s systems, ensuring data integrity and timely fulfillment for members.
• Research and resolve service interruptions, billing discrepancies, and subscription issues with a solutions-oriented mindset and a high level of attention to detail.
• Actively participate in ongoing training sessions, performance management programs, and cross-functional workgroups focused on continuous service improvement.
• Contribute to service center improvement projects by sharing ideas, identifying trends in member feedback, and supporting the rollout of new tools and processes.
• Maintain accurate documentation of member interactions, sales outcomes, and service resolutions in the appropriate CRM and service center platforms.
• Meet and exceed individual and team performance metrics related to call volume, quality, upsell conversion, and member satisfaction.

Essential Qualifications

• Bachelor’s degree preferred, OR a minimum of 3+ years of customer service and/or telemarketing experience in lieu of a degree.
• At least 2 years of upselling experience in a structured sales or service environment (required).
• At least 2 years of call center experience handling a high volume of inbound and outbound calls (required).
• At least 3 years of customer service experience in a professional setting (required).
• Experience using service center tools such as telephony platforms, performance measurement dashboards, and customer relationship management (CRM) applications.
• Excellent oral communication skills with demonstrated experience communicating professionally both by phone and in writing via email.
• Ability to work effectively in a high-volume, production-oriented, metrics-driven environment.
• Willingness and ability to travel to the Chicago office 6 to 8 times per year for organizational events, training sessions, and team meetings (required).
• Reliable home office setup with a quiet, professional space suitable for taking member calls.

Preferred Qualifications

• Prior sales experience in an outbound call environment with a track record of meeting or exceeding upsell targets.
• Experience supporting members of professional associations, healthcare organizations, or subscription-based services.
• Familiarity with membership management systems, subscription billing platforms, or association management software.
• Comfort with continuous training, coaching, and performance feedback in a structured contact center setting.

Skills and Competencies for Success

• Member-Centric Mindset: A genuine commitment to exceeding service expectations and treating every member interaction as an opportunity to add value.
• Sales Acumen: Confidence in identifying upsell and cross-sell opportunities, articulating the benefits of additional products or services, and closing on member needs.
• Verbal Communication: A clear, polished, and professional phone presence with the ability to explain complex information in an accessible way.
• Written Communication: Strong email writing skills with attention to tone, clarity, and accuracy.
• Problem Solving: Strong analytical and research skills with the ability to investigate issues, identify root causes, and deliver timely resolutions.
• Adaptability: Comfort with changing priorities, new products, evolving scripts, and shifting sales campaigns.
• Tech Fluency: Ability to navigate multiple systems simultaneously, including CRM tools, telephony software, knowledge bases, and internal applications.
• Resilience: A positive, patient, and persistent approach in a high-volume environment where metrics and quality matter equally.
• Collaboration: A team-oriented attitude with the willingness to contribute to group discussions, projects, and shared goals.

Career Growth and Learning Opportunities

At arenaflex, we believe customer service is a career, not just a job. As a Customer Service Representative III, you will have access to structured onboarding, ongoing coaching, and continuous learning opportunities that deepen your expertise in member engagement, consultative sales, and association operations. High performers have a clear pathway to permanent employment, expanded responsibilities, and potential advancement into senior service, team lead, or account management roles within the broader arenaflex organization. You will also gain valuable experience working alongside a respected medical association, building a résumé that stands out in the customer service and member engagement space.

Work Environment and Company Culture

arenaflex fosters a culture built on respect, inclusion, and shared purpose. We are deeply committed to diversity, equity, and inclusion in every aspect of our business, and we celebrate the unique perspectives each team member brings to the table. Our remote-first model gives you the flexibility to do your best work from home, while our quarterly onsite gatherings in Chicago create meaningful opportunities to connect face-to-face, collaborate on strategy, and celebrate wins as a team. You will be supported by approachable leadership, engaged peers, and a service center culture that values recognition, feedback, and continuous improvement.

Compensation, Perks, and Benefits

• Starting pay of $22.00 to $23.00 per hour, with a projected annual salary of $45,000 to $48,000 upon conversion to a permanent role.
• Full-time schedule of 37.5 expected hours per week, Monday through Friday, 8:30am to 5:00pm CST.
• Health insurance benefits available.
• Work from home with a consistent day shift schedule and no weekends.
• Temp-to-perm pathway with long-term career potential at arenaflex.
• Paid travel and onsite coordination for the 6 to 8 annual Chicago events.
• Supportive leadership, structured training, and a culture that recognizes and rewards performance.

How to Apply

If you are a driven customer service professional with a passion for member engagement, a knack for consultative sales, and the flexibility to travel to Chicago a handful of times each year, we invite you to apply today. Join arenaflex and become part of a team that is redefining what exceptional service looks like for one of the most respected medical associations in the country. Bring your voice, your talent, and your commitment to excellence, and let’s build something meaningful together at arenaflex.