Senior B2B Customer Success Manager – Enterprise Client Retention, Upsell & Growth Strategy | Orlando, FL

About arenaflex

arenaflex is a global leader in digital marketplaces, empowering millions of freelancers and businesses to collaborate, innovate, and thrive. With a vibrant community spanning more than 200 countries, arenaflex delivers cutting‑edge tools that simplify project sourcing, streamline payments, and drive measurable outcomes for both buyers and sellers. Our rapid growth is fueled by a culture that celebrates diversity, champions creativity, and places the customer experience at the heart of every decision.

Based in Orlando, Florida, our regional hub serves as a strategic nexus for B2B engagements across North America. We are on a mission to expand our enterprise footprint, helping large‑scale organizations unlock the full potential of our marketplace while ensuring they achieve sustained ROI through strategic partnership, proactive support, and data‑driven insights.

Why This Role Matters

As a B2B Customer Success Manager at arenaflex, you will be the trusted advisor for our most valuable enterprise accounts. You will own the end‑to‑end success journey—from onboarding and adoption to renewal and expansion—ensuring each client realizes the maximum value from arenaflex’s suite of solutions. Your ability to blend strategic thinking with hands‑on execution will directly influence customer retention rates, revenue growth, and the overall health of our B2B ecosystem.

Key Responsibilities

• Strategic Account Ownership: Serve as the primary point of contact for a portfolio of high‑value B2B customers, developing deep, consultative relationships built on trust and business insight.
• Customer Journey Mapping: Design, implement, and continually refine customized success plans that align with each client’s objectives, milestones, and KPIs.
• Retention & Expansion: Proactively identify renewal opportunities, upsell and cross‑sell additional arenaflex solutions, and execute growth strategies that increase account spend by at least 15% YoY.
• Data‑Driven Advocacy: Leverage analytics, usage data, and performance dashboards to surface actionable insights, demonstrate ROI, and guide strategic decision‑making for clients.
• Cross‑Functional Collaboration: Partner closely with Sales, Product, Marketing, and Engineering teams to convey client feedback, influence product roadmaps, and orchestrate seamless issue resolution.
• Onboarding Excellence: Lead comprehensive onboarding programs that accelerate time‑to‑value, ensuring new enterprise customers are fully configured, trained, and enabled within the first 90 days.
• Voice of the Customer: Champion the client’s perspective internally, facilitating regular business reviews, satisfaction surveys, and executive briefings.
• Risk Management: Identify early signs of churn, develop mitigation plans, and engage senior leadership when necessary to preserve account health.
• Thought Leadership: Conduct webinars, workshops, and best‑practice sessions that position arenaflex as a strategic partner and thought leader in the gig‑economy space.

Essential Qualifications

• 5+ years of proven experience in B2B customer success, account management, or enterprise sales enablement, preferably within SaaS, digital marketplaces, or technology platforms.
• Demonstrated track record of achieving high renewal rates (≥90%) and driving measurable account expansion.
• Strong analytical mindset with proficiency in CRM tools (e.g., Salesforce, HubSpot) and data visualization platforms (e.g., Tableau, Looker).
• Exceptional communication and presentation skills, capable of influencing C‑level stakeholders and articulating complex concepts with clarity.
• Bachelor’s degree in Business, Marketing, Computer Science, or a related field; an MBA or advanced degree is a plus.
• Ability to thrive in a fast‑paced, results‑oriented environment while maintaining a customer‑centric focus.

Preferred Qualifications

• Experience working with freelance or gig‑economy platforms, understanding the unique dynamics of supply‑demand marketplaces.
• Certification in Customer Success (e.g., SuccessCOACH, Pulse Academy) or related professional credentials.
• Multilingual capabilities, especially Spanish or Portuguese, to support diverse enterprise bases.
• Background in product management or consulting, enabling deeper empathy for client product challenges.

Core Skills & Competencies

• Relationship Management: Ability to build and nurture long‑term partnerships based on trust, transparency, and mutual success.
• Strategic Thinking: Skill in aligning customer goals with arenaflex’s product roadmap and business objectives.
• Problem Solving: Proactive identification of challenges and delivery of innovative, data‑backed solutions.
• Project Management: Expertise in coordinating multi‑department initiatives, meeting deadlines, and delivering on commitments.
• Negotiation & Influence: Comfortable navigating complex contract discussions and driving consensus across stakeholders.
• Adaptability: Comfortable with evolving technology trends, market shifts, and internal process improvements.
• Technical Literacy: Familiarity with APIs, integrations, and platform architecture to help clients leverage arenaflex’s technical capabilities.

Career Growth & Learning Opportunities

At arenaflex, your professional development is a priority. In this role, you will have access to:

• Leadership Pathways: Clear tracks toward Senior Customer Success Manager, Customer Success Team Lead, or Director of Enterprise Success.
• Continuous Learning: Company‑sponsored certifications, workshops, and conferences in customer success, data analytics, and SaaS strategy.
• Mentorship Programs: Pairing with senior leaders and industry experts to accelerate skill acquisition and career acceleration.
• Cross‑Functional Exposure: Rotational projects with Product, Marketing, and Sales to broaden business acumen and influence product direction.

Work Environment & Culture at arenaflex

Our Orlando office embodies a collaborative, inclusive, and high‑energy atmosphere. We believe that diverse perspectives fuel innovation, so we actively champion:

• Inclusivity: Employee resource groups, flexible holidays, and a zero‑tolerance policy for discrimination.
• Flexibility: Hybrid work model—three days in‑office, two days remote—supported by cutting‑edge collaboration tools.
• Well‑Being: On‑site fitness center, wellness stipends, mental‑health resources, and regular community‑building events.
• Transparency: Quarterly town halls with executive leadership, open‑door policy, and transparent performance metrics.

Compensation, Perks & Benefits

arenaflex offers a competitive total rewards package designed to attract and retain top talent:

• Base salary commensurate with experience, positioned in the top quartile of the Orlando market for B2B success roles.
• Performance‑based bonuses tied to renewal, expansion, and overall account health metrics.
• Equity participation through stock options or RSUs, aligning your success with arenaflex’s growth.
• Comprehensive medical, dental, and vision coverage for you and eligible dependents.
• Generous 401(k) plan with company match, plus financial wellness resources.
• Paid time off (PTO) policy, parental leave, and sabbatical options after five years of service.
• Professional development stipend, tuition reimbursement, and access to industry certifications.
• Employee assistance program, wellness challenges, and quarterly team outings.

How to Apply

If you are passionate about driving enterprise success, enjoy working at the intersection of technology and business, and thrive in a dynamic, customer‑centric environment, we want to hear from you. Join arenaflex and become a catalyst for growth, helping world‑class organizations unlock new possibilities on a global marketplace platform.

Take the next step in your career—apply today and embark on a rewarding journey with arenaflex!