Technical Customer Success Manager – Enterprise & Mid-Market Client Growth, Relationship Strategy, and Revenue Expansion at arenaflex

Join arenaflex as a Technical Customer Success Manager – Drive Long-Term Value for Enterprise & Mid-Market Partners

Are you passionate about turning complex technology into tangible business outcomes? Do you excel at building trusted relationships with senior decision-makers while simultaneously driving revenue growth, reducing churn, and championing the voice of the customer? arenaflex is searching for a dynamic, technically fluent Technical Customer Success Manager (CSM) to lead post-sale relationships with our most strategic Enterprise and mid-market merchants. This is more than a customer success role — it is an opportunity to sit at the intersection of product, sales, and customer experience, directly shaping how arenaflex delivers value across a fast-growing portfolio of leading brands.

At arenaflex, we are redefining how modern companies offer and manage finance solutions at scale. Our platform empowers merchants to provide seamless, frictionless lending experiences to their own customers, unlocking new revenue streams and elevating brand loyalty. As a member of our Customer Success team, you will play a pivotal role in ensuring that every merchant we serve realizes the full potential of our technology — from initial onboarding through long-term expansion. If you are energized by fast-paced environments, thrive on cross-functional collaboration, and want your work to have a measurable company-wide impact, we want to hear from you.

About the Role

As a Technical Customer Success Manager at arenaflex, you will own a portfolio of Enterprise and mid-market merchant accounts, serving as their primary strategic advisor, technical liaison, and growth partner. You will be responsible for the entire post-sale customer journey — from kickoff and adoption through renewal, expansion, and advocacy. Your mission is to deeply understand each customer's business objectives, align our platform capabilities to those goals, and proactively identify opportunities to deepen the partnership.

You will be a leader within the arenaflex Customer Success organization, working hand-in-hand with Sales, Product, Engineering, Marketing, and Support to ensure every customer experience is world-class. Your ability to communicate technical concepts to business stakeholders, and conversely translate business feedback into product insights, will be central to your success. The merchants you support will view you as a trusted extension of their own teams, and arenaflex leadership will look to you for actionable intelligence on customer health, market trends, and product opportunities.

Key Responsibilities

• Own a portfolio of Enterprise and mid-market merchant accounts, serving as the single point of contact for all post-sale activities including onboarding, adoption, expansion, and renewal.
• Build and nurture executive-level relationships with customer stakeholders, including C-suite leaders, VPs of eCommerce, product owners, and technical decision-makers.
• Conduct deep discovery and quarterly business reviews (QBRs) to understand each customer's business model, strategic priorities, competitive landscape, and success metrics.
• Develop and execute tailored success plans for each account, mapping arenaflex capabilities to customer outcomes and defining clear milestones for value realization.
• Drive product adoption and engagement by leading training sessions, workshops, and ongoing enablement initiatives tailored to both technical and non-technical audiences.
• Identify upsell and cross-sell opportunities by understanding customer growth trajectories and positioning additional arenaflex products, features, and services to meet evolving needs.
• Reduce churn and maximize customer lifetime value through proactive risk identification, mitigation strategies, and escalation management when issues arise.
• Act as the voice of the customer internally, channeling structured feedback to Product, Engineering, and Marketing teams to influence roadmap priorities and feature development.
• Collaborate with Sales on renewal forecasting, account expansion strategy, and commercial negotiations to support healthy, predictable revenue growth.
• Partner with Technical Support and Integrations teams to ensure smooth deployments, troubleshoot complex issues, and maintain high customer satisfaction throughout the technical lifecycle.
• Track and report on key customer success metrics, including Net Promoter Score (NPS), Customer Health Score, product usage, renewal rates, and expansion revenue.
• Represent arenaflex at industry events, webinars, and customer conferences, serving as a brand ambassador and thought leader in the customer success and fintech communities.
• Mentor and contribute to the development of best practices within the broader Customer Success organization, helping to scale our processes, playbooks, and tooling as we grow.

Essential Qualifications

• 5+ years of experience in Customer Success, Account Management, or a related client-facing role, preferably within B2B SaaS, fintech, payments, or eCommerce technology companies.
• Proven track record of managing Enterprise and mid-market accounts, including direct engagement with senior and executive-level stakeholders.
• Strong technical aptitude — comfortable discussing APIs, integrations, data flows, and platform architecture with engineering teams and translating those concepts for business audiences.
• Exceptional communication, presentation, and storytelling skills, with the ability to craft compelling narratives around customer outcomes and product value.
• Demonstrated success in driving revenue growth through upsell, cross-sell, and account expansion initiatives.
• Experience with customer success platforms such as Gainsight, Totango, ChurnZero, or equivalent tools, along with strong CRM proficiency (Salesforce, HubSpot, etc.).
• Analytical mindset with the ability to interpret customer data, usage trends, and health scores to inform strategy.
• Self-starter mentality with the ability to thrive in a fast-paced, high-growth, and evolving environment.

Preferred Qualifications

• Background in fintech, lending, payments, or point-of-sale financing is a strong plus.
• Experience working with multi-stakeholder enterprise implementations involving complex integrations and cross-functional project teams.
• Familiarity with API-driven platforms, webhooks, SDKs, and technical onboarding workflows.
• Prior experience contributing to product roadmap discussions based on customer feedback and market intelligence.
• Multilingual abilities or experience supporting global customer bases.

Skills and Competencies for Success

• Relationship Building: You build trust quickly, develop rapport with diverse stakeholders, and serve as a genuine partner to your customers.
• Strategic Thinking: You see beyond the immediate task, understanding how each account fits into the broader customer journey and arenaflex growth strategy.
• Technical Fluency: You can hold credible conversations with engineers while also inspiring confidence in non-technical executives.
• Influence and Negotiation: You navigate complex commercial discussions with poise, professionalism, and a focus on mutually beneficial outcomes.
• Problem Solving: You approach challenges with curiosity, resourcefulness, and a bias for action.
• Resilience and Adaptability: You perform exceptionally in dynamic environments where priorities can shift quickly.
• Collaboration: You actively contribute to team success, share knowledge generously, and elevate those around you.

Career Growth and Learning Opportunities

At arenaflex, we believe that our Customer Success team is a strategic engine of growth — both for our customers and for our company. As a Technical CSM, you will have direct exposure to executive leadership, product strategy, and revenue operations, providing a unique vantage point for long-term career development. We invest heavily in our people through:

• Structured onboarding and continuous learning programs designed to accelerate your ramp and deepen your expertise.
• Access to mentorship from senior leaders across Customer Success, Product, and Sales.
• Opportunities to specialize or broaden your scope into roles such as Senior CSM, CSM Team Lead, Product Management, Solutions Engineering, or Strategic Account Management.
• Annual budget for professional development, certifications, and conference attendance.
• A clear and transparent career progression framework with regular performance reviews and growth conversations.

Work Environment and Company Culture at arenaflex

arenaflex is a remote-friendly, globally distributed company united by a shared mission: to revolutionize the way companies offer finance solutions. Our culture is built on trust, ownership, curiosity, and a relentless commitment to customer impact. We move fast, embrace feedback, and celebrate wins big and small. You will join a diverse, collaborative, and highly skilled team that genuinely cares about doing meaningful work and supporting one another along the way. Whether you are collaborating asynchronously across time zones or brainstorming in real time, you will find an environment that empowers you to do your best work.

Compensation, Perks, and Benefits

While specific compensation will be tailored based on experience, location, and role level, arenaflex offers a competitive total rewards package that includes:

• Competitive base salary aligned with market benchmarks.
• Performance-based bonuses or commission tied to customer success and expansion metrics.
• Equity opportunities so every team member can share in the company's long-term success.
• Comprehensive health, dental, and vision coverage (where applicable).
• Generous paid time off, including vacation, sick days, and company holidays.
• Flexible work arrangements that support work-life balance.
• Home office stipend and wellness benefits to support your best work setup.
• Parental leave and family support programs.
• Retirement or savings plans with potential employer contributions.

Why arenaflex?

Joining arenaflex means joining a company that is at the forefront of a rapidly evolving industry. Our product is changing how merchants connect consumers with the financing they need — and our Customer Success team is the bridge that turns great technology into lasting customer outcomes. If you are an experienced customer success professional who thrives on building relationships, driving measurable results, and working with cutting-edge technology, arenaflex offers the platform, the people, and the purpose to take your career to the next level.

How to Apply

Ready to make an impact? We would love to hear from you. Submit your resume and a brief cover letter highlighting your experience managing technical customer relationships and driving enterprise growth. arenaflex is an equal opportunity employer. We celebrate diversity and are committed to building an inclusive environment for all employees.