Director of Customer Success – Merchant Services & Payments Portfolio Leadership

About arenaflex

arenaflex is a market‑leading fintech platform that transforms traditional accounts receivable (AR) processes into a strategic advantage for businesses of all sizes. In a world where cash flow delays can cripple growth, arenaflex removes friction, unlocks working capital, and accelerates financial momentum for finance leaders across the globe. By automating AR, reconciling B2B payments, and unifying finance teams, customers, and core business systems into a single, intelligent ecosystem, arenaflex delivers unprecedented clarity and control over cash flow.

With more than 10,000 active customers, over 5 million companies transacting on the platform, and a transaction volume exceeding 110 million payments that represent $257 billion in annual processed value, arenaflex is at the forefront of the payments revolution. Our mission is to empower finance teams to focus on strategic growth rather than chasing paperwork, and we do this by building technology that is both powerful and intuitive.

We are looking for a visionary leader who can shape the future of our Merchant Services portfolio, drive customer advocacy, and ensure that every client experiences the full benefit of arenaflex’s innovative solutions.

Why This Role Matters – Your Impact on arenaflex and Your Career

As the Director of Customer Success – Merchant Services you will own the strategic vision for customer success, retention, and expansion across our enterprise merchant portfolio. Reporting directly to the Vice President of Customer Success, you will build and mentor a high‑performing team of Customer Success Managers (CSMs), establish scalable best practices, and partner with senior leadership to align success initiatives with arenaflex’s growth objectives. Your deep expertise in merchant services and payments will be the catalyst for innovative programs that elevate the customer experience and drive measurable revenue outcomes.

Key Responsibilities

Strategic Leadership

• Recruit, develop, and scale a world‑class team of CSMs, defining clear goals, KPIs, and individualized career paths.
• Craft and execute a multi‑year strategic roadmap for customer success, encompassing retention, expansion, and advocacy initiatives.
• Collaborate with the executive team to ensure that customer success strategies are tightly integrated with overall corporate objectives and financial targets.
• Design repeatable, scalable processes that guarantee consistent, high‑quality interactions across the entire customer lifecycle.

Revenue & Portfolio Management

• Own portfolio revenue targets, including renewal rates, expansion (upsell/cross‑sell) goals, and overall customer health metrics.
• Implement a strategic account planning framework that drives proactive engagement with high‑value merchants.
• Develop predictive analytics and early‑warning systems to identify at‑risk accounts and uncover growth opportunities.
• Maintain executive‑level relationships with strategic customers, leading negotiations, issue resolution, and partnership development.

Cross‑Functional Collaboration

• Partner with Product, Sales, and Professional Services leaders to ensure that customer insights directly influence product roadmaps and go‑to‑market strategies.
• Work closely with Finance to build forecasting models, performance dashboards, and financial metrics that reflect the impact of customer success initiatives.
• Lead change‑management projects that improve operational efficiency, reduce churn, and enhance the overall customer experience.
• Select, implement, and optimize the technology stack (CRM, CS platforms, BI tools) that empowers the CSM team to scale effectively.

Program Development & Execution

• Design and oversee comprehensive onboarding, training, and adoption programs that accelerate time‑to‑value for new merchants.
• Standardize Executive Business Reviews (EBRs) and strategic account planning sessions to drive alignment and measurable outcomes.
• Launch voice‑of‑customer initiatives that capture feedback, translate insights into action, and foster a culture of continuous improvement.
• Build robust customer health scoring models and success metrics that provide real‑time visibility into account performance.

Essential Qualifications

• Minimum 8 years of experience in customer success, with at least 3 years in a leadership capacity, preferably within B2B merchant services, payment acquiring, PayFac, or ISO environments.
• Demonstrated success in building, scaling, and leading high‑performing CSM teams in fast‑growth, SaaS‑driven organizations.
• Bachelor’s degree in Business, Finance, Technology, or a related field; advanced degree or relevant certifications are a plus.
• Deep understanding of payment technologies, merchant services ecosystems, and enterprise software integration.
• Proven ability to develop and execute data‑driven strategies that improve retention, expansion, and overall customer health.

Preferred Qualifications & Additional Skills

• Experience with SaaS metrics such as Net Revenue Retention (NRR), Customer Lifetime Value (CLV), and churn analysis.
• Advanced proficiency with CRM platforms (e.g., Salesforce), customer success tools (e.g., Gainsight, Totango), and business intelligence solutions (e.g., Tableau, Power BI).
• Strong analytical mindset with a track record of leveraging data to drive strategic decisions and operational improvements.
• Exceptional communication and executive presence, capable of influencing senior stakeholders both internally and externally.
• Demonstrated ability to lead cross‑functional initiatives that result in product enhancements, process efficiencies, and revenue growth.

Core Competencies & Personal Attributes

• Customer Obsession: A relentless focus on delivering value to customers and championing their success across the organization.
• Strategic Vision: Ability to think long‑term, anticipate market trends, and translate insights into actionable plans.
• Leadership & Mentorship: Proven talent for inspiring teams, fostering a culture of accountability, and developing future leaders.
• Innovation: Comfortable experimenting with new approaches, tools, and processes to stay ahead of industry evolution.
• Results Orientation: Commitment to achieving measurable outcomes while maintaining high standards of quality and integrity.

Career Growth & Learning Opportunities

arenaflex invests heavily in the professional development of its leaders. As Director of Customer Success, you will have access to:

• Executive mentorship programs that connect you with senior leaders across finance, product, and go‑to‑market functions.
• Continuous learning budgets for certifications, conferences, and advanced training in payments, SaaS, and leadership.
• Opportunities to shape company‑wide initiatives, influence product strategy, and drive enterprise‑level change.
• A clear promotion pathway toward senior director and VP‑level roles, based on performance and impact.

Culture & Work Environment at arenaflex

arenaflex cultivates a collaborative, inclusive, and high‑energy environment where innovation thrives. Our core values—Customer Success, Integrity, Agility, and Impact—guide everything we do. Employees enjoy:

• Flexible remote‑first work arrangements, with occasional in‑person gatherings to strengthen team bonds.
• A transparent leadership style that encourages open dialogue, idea sharing, and rapid decision‑making.
• A diverse, global workforce that celebrates different perspectives and backgrounds.
• Recognition programs that celebrate both individual achievements and team milestones.

Compensation, Perks, & Benefits

arenaflex offers a competitive total‑target compensation package that reflects the seniority and impact of this role. While exact figures may vary based on experience, the package typically includes:

• Base salary complemented by performance‑based bonuses and equity participation.
• Comprehensive health, dental, and vision coverage for you and your dependents.
• Generous paid time off, parental leave, and flexible holiday policies.
• Retirement savings plans with company matching contributions.
• Professional development stipend, wellness programs, and employee assistance resources.
• State‑of‑the‑art home office allowance and technology reimbursement.

How to Apply

If you are ready to lead a high‑impact team, shape the future of merchant services, and drive transformative results for arenaflex’s customers, we want to hear from you. Click the link below to submit your application and join a company that is redefining the financial landscape.

Apply to this Job

Join arenaflex – Where Your Vision Becomes Reality

At arenaflex, your expertise will be celebrated, your ideas will be heard, and your leadership will directly influence the success of thousands of businesses worldwide. Take the next step in your career and become a catalyst for growth, innovation, and customer delight. Apply today and help us turn accounts receivable into a competitive advantage for the next generation of enterprises.