Director, Senior Customer Success Leader – Merchant Services & Payments Portfolio Strategy
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. Our cloud‑native, AI‑enhanced solutions automate the entire AR lifecycle—connecting finance teams, merchants, and enterprise systems into a single, transparent ecosystem.
With more than 10,000 active customers and over five million companies transacting on our platform, arenaflex processes in excess of 110 million transactions and $257 billion in annual payment volume. Our mission is to empower organizations to gain real‑time clarity, improve cash conversion, and drive sustainable growth. As we continue to expand our merchant services portfolio, we are looking for a visionary leader who can shape the future of customer success and champion the voice of our most valuable partners.
Why This Role Matters – Your Impact on arenaflex and Your Career
As the Director of Customer Success – Merchant Services at arenaflex, you will own the strategic vision and execution of customer success for 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), design scalable processes, and partner with senior leadership to align success initiatives with corporate growth objectives. Your work will directly influence revenue retention, expansion, and the overall health of our most strategic accounts, positioning arenaflex as the trusted partner for merchants worldwide.
This role offers a unique blend of strategic influence, hands‑on leadership, and cross‑functional collaboration. You will have the opportunity to shape industry‑defining programs, work closely with product and engineering to embed merchant insights into the roadmap, and drive measurable business outcomes that accelerate both your career and arenaflex’s market leadership.
Key Responsibilities
Strategic Leadership
- Recruit, develop, and scale a world‑class team of Customer Success Managers, establishing clear performance metrics, career pathways, and a culture of continuous improvement.
- Define and execute a multi‑year strategic roadmap for customer success, encompassing retention, expansion, and advocacy programs tailored to the merchant services segment.
- Partner with the executive team to ensure that customer success initiatives are tightly integrated with arenaflex’s overall growth strategy and financial targets.
- Design repeatable, scalable processes that deliver consistent, high‑quality experiences for every merchant, from onboarding through renewal.
Revenue & Portfolio Management
- Own portfolio revenue targets, including net retention, expansion, and churn reduction, and drive accountability across the CSM team.
- Implement strategic account planning frameworks that align with each merchant’s business objectives, ensuring proactive engagement and value delivery.
- Develop predictive health indicators and early‑warning systems to surface at‑risk accounts and uncover upsell opportunities.
- Maintain executive relationships with key merchant stakeholders, leading high‑stakes negotiations, renewal discussions, and issue resolution.
Cross‑Functional Collaboration
- Work closely with Product, Sales, and Professional Services leaders to translate merchant feedback into product enhancements and go‑to‑market strategies.
- Collaborate with Finance to build robust forecasting models, KPI dashboards, and financial metrics that reflect the impact of customer success initiatives.
- Lead change‑management initiatives that streamline internal workflows, improve team efficiency, and elevate 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 launch comprehensive onboarding, training, and adoption programs that accelerate time‑to‑value for new merchants.
- Establish best‑practice frameworks for Executive Business Reviews (EBRs) and strategic account planning, ensuring each interaction drives measurable outcomes.
- Create a Voice‑of‑Customer (VoC) program that captures, analyzes, and acts on merchant feedback to continuously improve the arenaflex platform.
- Develop and maintain a robust customer health scoring system, integrating usage data, financial metrics, and sentiment analysis.
Qualifications – What We’re Looking For
Experience & Education
- Minimum 8 years of experience in customer success, with at least 3 years in a leadership capacity overseeing enterprise‑level accounts.
- Deep expertise in Merchant Services, including experience with payment acquirers, Payfac models, and ISO environments.
- Proven track record of building, scaling, and leading high‑performing customer success teams in fast‑growth, SaaS‑driven organizations.
- Bachelor’s degree in Business, Finance, Technology, or a related field; advanced degree or relevant certifications (e.g., CSPO, CSM) are a plus.
Leadership Competencies
- Strategic Vision: Ability to craft long‑term strategies that align customer success with broader business objectives and drive sustainable growth.
- Team Development: Demonstrated skill in coaching, mentoring, and empowering teams to achieve high performance and career advancement.
- Executive Presence: Strong communication and influencing skills, capable of engaging C‑suite executives both within arenaflex and at merchant organizations.
- Business Acumen: Deep understanding of SaaS economics, ARR, churn, and the financial levers that drive customer success profitability.
Technical & Analytical Skills
- Solid grasp of payment technologies, merchant services workflows, and enterprise software integrations.
- Data‑driven decision‑making mindset, with hands‑on experience using CRM platforms (e.g., Salesforce), CS tools (e.g., Gainsight, Totango), and BI solutions (e.g., Tableau, Power BI).
- Experience building predictive models, health scores, and analytics dashboards to inform proactive engagement strategies.
- Familiarity with change‑management methodologies (e.g., ADKAR, Prosci) and process‑improvement frameworks (e.g., Lean, Six Sigma).
Personal Qualities
- Customer Obsession: A relentless focus on delivering value and delight to merchants, fostering a culture where the customer’s voice drives every decision.
- Strategic Thinking: Ability to balance long‑term vision with short‑term execution, navigating complex stakeholder landscapes.
- Innovation: Forward‑looking mindset that anticipates industry trends and proactively evolves the customer success function.
- Results Orientation: Commitment to achieving measurable outcomes while maintaining the highest standards of quality and professionalism.
Compensation, Benefits & Perks
arenaflex offers a competitive total‑target compensation package that reflects the seniority and impact of this role. The OTE range is between $200,000 – $230,000 CAD, complemented by a performance‑based bonus structure tied to portfolio health and revenue growth.
Our benefits suite includes:
- Comprehensive health, dental, and vision coverage for you and your dependents.
- Generous paid time off, parental leave, and flexible holiday policies.
- Remote‑first work model with a home‑office stipend and access to coworking spaces worldwide.
- Professional development budget, tuition reimbursement, and access to industry conferences.
- Retirement savings plans with company matching, employee stock purchase options, and financial wellness resources.
- Wellness programs, mental‑health support, and employee assistance services.
Culture & Work Environment at arenaflex
At arenaflex, we champion a culture of collaboration, curiosity, and continuous improvement. Our teams are empowered to experiment, learn, and iterate quickly, fostering an environment where innovative ideas thrive. We value diversity of thought and background, believing that inclusive teams deliver the best outcomes for our merchants and shareholders.
Key cultural pillars include:
- Customer‑Centricity: Every decision is filtered through the lens of merchant impact.
- Data‑Driven Excellence: We rely on metrics, insights, and rigorous analysis to guide strategy.
- Ownership & Accountability: Employees are trusted to own outcomes and are recognized for delivering results.
- Growth Mindset: Continuous learning is encouraged through mentorship, internal mobility, and knowledge‑sharing forums.
- Transparency: Open communication channels with leadership ensure alignment and shared purpose.
Career Growth & Development Opportunities
Joining arenaflex as a Director of Customer Success positions you at the nexus of product, finance, and market strategy. You will gain exposure to senior leadership, influence multi‑million‑dollar revenue streams, and shape the future of merchant services innovation. Success in this role can lead to senior executive pathways such as Vice President of Customer Success, Chief Customer Officer, or General Manager of the Merchant Services Division.
We invest heavily in your professional journey, offering:
- Executive coaching and leadership development programs.
- Cross‑functional project assignments that broaden your business acumen.
- Mentorship from industry veterans and access to a global network of fintech thought leaders.
- Opportunities to present at industry events, publish thought pieces, and represent arenaflex in strategic partnerships.
Application Process & Next Steps
If you are a strategic, data‑savvy leader with a passion for merchant services and a track record of building world‑class customer success teams, we want to hear from you. Apply today to join arenaflex’s mission‑driven team and help shape the future of payments and cash‑flow optimization.
We review applications on a rolling basis and will reach out to qualified candidates to schedule an initial conversation. Please ensure your resume highlights relevant leadership experience, merchant services expertise, and measurable outcomes.
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