Customer Success Specialist – Life Insurance Platform Operations & Client Enablement (Remote)

About arenaflex

arenaflex is a forward-thinking joint venture reimagining the way financial representatives sell and service life insurance across the United States. We are building a modern, process-driven operating system that consolidates the tangled web of four to seven legacy software tools into one cohesive, automated platform. Our mission is ambitious yet vital: to bring life insurance services firmly into the 21st century, supporting the more than 40 million American households who lack sufficient financial protection to weather life's inevitable hardships.

The insurance industry has long been defined by manual workflows, fragmented systems, and outdated technology. arenaflex exists to change that. Already adopted by one of the nation's most respected financial planning and advisory firms, our platform is on track to modernize operations that drive more than $50 billion in annual revenue. Backed by significant capital from a strategic partner and the resources of being part of the broader arenaflex family — an award-winning organization recognized as a Best Place to Work, a 5-Star Diversity, Equity, and Inclusion award recipient, and a WORK180 endorsed employer — we are uniquely positioned to lead this transformation.

At arenaflex, we believe the right technology can empower advisors to focus on what they do best: helping families and businesses secure their financial futures. If you are passionate about solving complex operational challenges and making a meaningful impact, we want you on our team.

The Opportunity

We are seeking a dedicated Customer Success Specialist – Life Insurance Platform Operations & Client Enablement to serve as the trusted first point of contact for our clients. This is not a traditional IT help desk role. Instead, you will operate at the intersection of customer support, product enablement, and operational excellence, guiding financial representatives through the nuances of our platform while helping them unlock its full potential.

Reporting to the Customer Success leadership team, you will play a critical role in onboarding new users, resolving technical and workflow-related inquiries, testing new features, and feeding customer insights back into our product roadmap. This is a fully remote position, ideally aligned with an Eastern or Central Time workday, and is suited to a self-motivated professional who thrives in a fast-paced, mission-driven environment.

Key Responsibilities

Customer Support & Issue Resolution

• Respond promptly and professionally to customer inquiries received via email, chat, and ticketing systems.
• Identify, diagnose, and resolve technical and workflow-related issues using a variety of tools, documentation, and problem-solving methodologies.
• Document all customer interactions, troubleshooting steps, and resolutions within our ticketing platform (Zendesk), ensuring records are accurate, comprehensive, and up to date.
• Escalate complex issues to appropriate internal teams (engineering, product, or account management) and collaborate closely to drive timely resolution.
• Follow up with customers to confirm resolution satisfaction and identify opportunities for further assistance.

Onboarding & Training

• Manage the end-to-end onboarding process for new users, ensuring they are configured, trained, and confident in using the platform from day one.
• Conduct engaging user training sessions and workshops, both live and recorded, covering best practices, new features, and system updates.
• Create, maintain, and continuously improve customer training materials, including step-by-step guides, one-pagers, and instructional videos.
• Train new arenaflex employees on product functionality, common user scenarios, and internal support processes.

Product Enablement & Quality Assurance

• Play a critical role in the release process by testing new features and fixes, performing smoke tests, and communicating detailed release notes across the organization.
• Participate in the refinement of bugs and user stories, ensuring the customer's voice is represented throughout the product development lifecycle.
• Stay continuously updated on product features, enhancements, and best practices, and proactively share this knowledge with both customers and internal colleagues.
• Build, document, and master customer success playbooks covering ticket management, client communication, escalations, and problem-solving.

Operational Excellence & Continuous Improvement

• Own and manage individual KPIs, consistently meeting service level agreements (SLAs) and quality benchmarks.
• Provide structured feedback and actionable suggestions to product and engineering teams based on recurring customer needs, pain points, and feature requests.
• Partner closely with Customer Success Managers (CSMs) to prioritize projects, issues, and customer roadmap initiatives.
• Identify opportunities to streamline internal processes and improve the overall customer experience.

Knowledge, Skills, and Abilities

• Communication Excellence: Outstanding written and verbal communication skills, with the ability to explain technical concepts clearly and simply to non-technical audiences.
• Customer-Centric Mindset: Demonstrated experience handling customer inquiries with empathy, professionalism, and a solutions-oriented approach.
• Problem-Solving Acumen: Strong analytical and troubleshooting skills, with the ability to resolve and document technical issues efficiently.
• Cross-Functional Collaboration: Proven ability to work effectively with technical stakeholders, including engineers, product managers, and account managers.
• Detail Orientation: Highly organized with the ability to prioritize multiple tasks, manage competing deadlines, and maintain meticulous records.
• Adaptability & Agility: Comfortable shifting priorities quickly in a dynamic, evolving startup environment.
• Self-Direction: Ability to work independently in a remote setting while staying connected to team goals and initiatives.

Education and Experience

• 2+ years of experience in business operations, customer support, technical account management, or a similar role.
• Prior experience in insurance software, financial technology, or a related domain is a significant plus.
• Familiarity with CRM systems, ticketing tools (preferably Zendesk), and remote support software.
• Technology support and troubleshooting experience is preferred.
• A college degree or equivalent advanced learning is preferred; a high school diploma or equivalent is required.

What We Offer

Compensation & Benefits

• Highly competitive base salary, with performance-based incentive opportunities.
• Generous paid time off (PTO) and paid company holidays.
• 401(k) plan with company match.
• Comprehensive health and wellness programs.
• Exclusive discount programs for employees and their families.

The base salary range for this position is $55,000 – $70,000, determined based on experience, credentials, education, certifications, skill level, scope of the position, and geographic location. Final offers are made on a case-by-case basis.

Growth & Impact

• An unparalleled opportunity to help change the life insurance landscape and improve financial security for millions of Americans.
• The chance to build something new with lasting value, shaping both the product and the operational culture from an early stage.
• Direct exposure to product development, customer strategy, and cross-functional leadership initiatives.
• Continuous learning opportunities, including training in cutting-edge insurance technology and customer success best practices.

Culture & Environment

• A people-first culture that nurtures lifelong relationships with employees, customers, and partners.
• A remote-first work environment that values flexibility, autonomy, and results.
• An inclusive, collaborative team committed to diversity, equity, and belonging.
• A supportive leadership team that invests in professional development and career growth.

Join Us

If you are energized by turning complex, labor-intensive workflows into elegant solutions, and you want to play a pivotal role in modernizing an entire industry, arenaflex is the place for you. As a Customer Success Specialist on our growing team, you will be the bridge between our innovative platform and the financial professionals who rely on it every day. Your work will directly impact the experience of users serving millions of American families, and your insights will help shape the future of our product.

Don’t miss this opportunity to join a well-capitalized, mission-driven company at the forefront of insurance technology. Apply today and help us build the future of financial services — together.

arenaflex is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.