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Posted Mar 4, 2026

Dynamic Customer Success Leader – Manager of Customer Success & Strategic Client Partnerships for Health Insurance Innovation

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```html About arenaflex – Transforming Health Insurance Through Innovation arenaflex is a fast‑growing startup on a bold mission to overhaul the health‑insurance landscape. By empowering employers to reimburse employees for individually chosen coverage rather than locking them into a one‑size‑fits‑all group plan, we are turning the traditional model on its head. Our approach gives employees the freedom to become savvy healthcare consumers while creating measurable cost efficiencies for employers. Health insurance has long been a source of frustration, confusion, and even anxiety. At arenaflex, we are fixing that problem with cutting‑edge technology, an intuitive user experience, and a relentless focus on outcomes. Since securing Series B funding in 2023, we have expanded rapidly, earned coverage in major publications such as The New York Times and The Wall Street Journal, and positioned ourselves as a recognized leader in the emerging ICHRA (Individual Coverage Health Reimbursement Arrangement) space. Our culture is built on transparency, collaboration, and a shared desire to make a tangible difference in the lives of millions. Diversity, equity, and inclusion are not just buzzwords; they are core to our success. If you thrive in an environment where purpose meets performance, arenaflex could be the perfect place for your next career chapter. Why This Role Matters – The Manager, Customer Success The Manager, Customer Success at arenaflex will helm a high‑performing team of Customer Success Managers (CSMs) who serve our ICHRA clients. As our clientele expands to larger employers with sophisticated needs, the role becomes pivotal in shaping strategic partnerships, driving adoption, and ensuring that every client experiences the full value of arenaflex’s platform. This is more than a management position—it’s a leadership opportunity to dictate the direction of client experience, influence product roadmaps, and champion a customer‑centric mindset across the organization. Key Responsibilities - Team Leadership & Development: Recruit, mentor, and coach a team of CSMs, providing regular performance feedback, career‑path guidance, and professional development resources. - Performance Management: Define, monitor, and iterate on team‑wide KPIs (e.g., Net Promoter Score, renewal rates, adoption metrics) to ensure alignment with arenaflex’s strategic objectives. - Playbook & Framework Optimization: Continuously refine the customer success playbook, incorporating best practices, data‑driven insights, and scalable processes. - Strategic Client Partnership: Build deep, consultative relationships with key client stakeholders, understanding their business objectives and aligning arenaflex solutions to drive measurable outcomes. - Cross‑Functional Collaboration: Partner with Product, Sales, Marketing, and Implementation teams to voice client needs, influence feature development, and create unified go‑to‑market strategies. - Escalation Management: Serve as the senior point of contact for complex client escalations, proactively troubleshooting issues and turning challenges into growth opportunities. - Data‑Driven Insights: Leverage analytics to surface trends, recommend improvements, and present strategic insights to senior leadership. - Advocacy & Thought Leadership: Represent arenaflex at industry events, webinars, and customer forums, positioning the company as a visionary leader in health‑benefit innovation. Essential Qualifications - 5+ years of experience in Customer Success, Account Management, or a client‑facing role within the health‑tech or SaaS industry. - Minimum of 3 years in a leadership capacity, with a proven record of building, coaching, and scaling high‑performing teams. - Demonstrated success in designing and executing a comprehensive Customer Success playbook that drives adoption, renewal, and expansion. - Strong strategic mindset with the ability to translate client goals into actionable plans and measurable results. - Excellent written and verbal communication skills; comfortable presenting to C‑suite executives and cross‑functional partners. - Highly organized, data‑driven, and comfortable managing multiple priorities in a fast‑moving startup environment. Preferred (But Not Required) Qualifications - Experience in health‑benefit administration, ICHRA, or related regulatory frameworks. - Background in product management or product‑customer liaison roles, providing insight into product lifecycle influence. - Familiarity with CRM and Customer Success platforms such as Gainsight, Totango, or Salesforce Service Cloud. - Track record of driving revenue growth through upsell and cross‑sell initiatives. - Previous exposure to Series B or later‑stage startup environments, understanding of scaling processes and culture. Core Skills & Competencies for Success - Leadership Presence: Ability to inspire, motivate, and align a diverse team around a shared vision of client excellence. - Analytical Acumen: Comfort with data analysis, reporting, and translating metrics into strategic action plans. - Empathy & Relationship Building: Deep understanding of client pain points, paired with the skill to craft tailored solutions. - Strategic Thinking: Visionary perspective to anticipate market trends and position arenaflex as a forward‑thinking partner. - Change Management: Expertise in guiding clients through adoption cycles, driving engagement, and minimizing churn. - Collaboration & Influence: Proven ability to work across product, sales, and marketing to champion client interests. Career Growth & Learning at arenaflex arenaflex invests heavily in the professional development of its people. As the Manager, Customer Success, you will have direct access to senior leadership, participate in strategic planning sessions, and influence the shape of our product roadmap. We offer: - Personalized learning plans and a stipend for external certifications (e.g., Certified Customer Success Manager). - Mentorship programs pairing you with industry veterans and internal thought leaders. - Opportunities to lead cross‑functional initiatives, gaining exposure to product development, go‑to‑market strategy, and investor relations. - A clear path to senior leadership roles, such as Director of Customer Success or VP of Customer Experience, as the organization scales. Compensation, Perks & Benefits Base Salary: $90,000 – $115,000 annually, commensurate with experience and proven impact. Performance Bonus: Up to 18% of base salary, tied to team KPIs, client retention, and revenue expansion. Benefits Include: - Comprehensive health, dental, and vision coverage—including a generously funded ICHRA for employees and their families. - Unlimited paid vacation plus company‑observed holidays, encouraging work‑life balance. - 401(k) plan with a 4% employer match (vested over four years after a 90‑day eligibility period). - Parental leave for new parents, recognizing the importance of family time. - Access to LinkedIn Learning and other professional development resources. - Modern office spaces in Richardson, TX (City Line) and Austin, TX (Holly Commons) equipped with collaborative zones, quiet phone rooms, and fully stocked kitchens. - Hybrid work model – we love seeing you in the office three days a week for white‑boarding sessions and relationship building, while also supporting remote work when you need focused time. - Employee discounts on arenaflex’s own health‑benefit platform, giving you first‑hand experience with the product you champion. Work Environment & Culture at arenaflex Our offices are designed for flexibility and creativity. Whether you prefer a relaxed couch area, a standing kiosk desk, or a quiet phone booth, you’ll find a space that matches your work style. The culture is built on transparency, curiosity, and a fearless approach to solving complex problems. We celebrate diverse perspectives and encourage every team member to bring their authentic self to work. Our leadership practices open communication, regular town‑halls, and feedback loops that empower employees to shape company direction. We believe that a happy, engaged team translates directly into happier clients. Commitment to Diversity, Equity & Inclusion arenaflex is an equal‑opportunity employer. We are dedicated to cultivating a workforce that reflects the rich diversity of the communities we serve. Our recruitment, development, and retention strategies focus on building an inclusive environment where every voice is heard and valued. Take the Next Step – Join arenaflex Today If you are a proactive, strategic thinker with a passion for delivering exceptional client experiences and you thrive in a fast‑moving, mission‑driven startup, we want to hear from you. This is your chance to shape the future of health‑insurance reimbursement, lead a talented team, and grow your career alongside an innovative, purpose‑focused organization. Apply now and become a part of the arenaflex story. Together, we’ll redefine how people access and experience health benefits. ```