**Director of Customer Success – Transformative Leadership Role at arenaflex**

**Join arenaflex, a venture-backed SaaS startup revolutionizing the retail sector, as we seek an exceptional Director of Customer Success to elevate and scale our existing Customer Success organization.** **About arenaflex** arenaflex is the leading performance platform for frontline retail teams in the cannabis industry, empowering real-time incentives, training, content, and analytics. We seamlessly integrate with POS systems to connect brands, retailers, and frontline employees, driving measurable sales lift and operational excellence. arenaflex is trusted by over 3000 businesses in the US. We're a fast-growing, venture-backed startup on a mission to transform how the $20T+ global retail sector collaborates, executes, and rewards performance. Our investors include TenOneTen Ventures, the creator of Google AdSense, and Jason Calacanis. **About the Role** We're seeking a visionary Director of Customer Success to lead, modernize, and scale our existing CS organization. With a team of ~10 experienced CSMs and support specialists already in place, this role isn't about building from scratch—it's about elevating and transforming a strong foundation into a high-performing, product-aligned, data-informed function. You'll lead a comprehensive overhaul of our customer journey, onboarding experience, success processes, internal tooling, and CS analytics infrastructure. This includes developing systems for cross-functional visibility (Product, Engineering, Sales), driving improved analytics and admin reporting, and ensuring white-glove onboarding and lifecycle management. This is a strategic leadership role with high autonomy, deep impact, and clear executive support. **Key Responsibilities:** • **Lead and Elevate a Customer Success Team**: Direct and develop a team of ~10 CSMs, support specialists, and onboarding experts across multiple customer segments. • **Redesign and Optimize Customer Journeys**: Develop and implement high-touch, account-based models for onboarding, engagement, retention, and expansion workflows. • **Implement Scalable Systems and Dashboards**: Design and deploy systems for improved reporting, performance analytics, account health visibility, and retention forecasting. • **Drive Alignment between CS and Product**: Systematize feedback loops, usage insights, and strategic account input to ensure seamless collaboration. • **Build Robust Playbooks and SLAs**: Develop a comprehensive set of playbooks, SLAs, and KPIs across the customer lifecycle to ensure CS becomes a predictable, high-performing engine. • **Serve as an Executive Voice for the Customer**: Regularly collaborate with Product, Engineering, and RevOps to ensure customer needs are met and exceeded. • **Guide Tooling Decisions and Integrations**: Oversee tooling decisions and integrations across Hubspot, Intercom, analytics platforms, and internal admin systems. • **Own Key Outcomes**: Drive NRR, time-to-value, onboarding conversion, CSAT, and churn reduction. **Essential Qualifications:** • **6–10+ years in Customer Success or Account Management**: Proven experience in leading and scaling teams in an early-stage B2B SaaS company. • **Deep Experience Overhauling CS Functions**: Ability to transform CS processes, reporting, playbooks, and org structure. • **Proven Ability to Lead Cross-Functional Initiatives**: Experience leading initiatives involving Product, Engineering, and Data teams. • **Passion for Building Systems and Structure**: Experience designing internal dashboards, forecasting, segmentation, and usage visibility. • **Exceptional Written and Verbal Communication**: Clear, precise, and persuasive communication with stakeholders at all levels. • **Tech-Savvy**: Fluency in tools like Hubspot, Intercom, Notion, and product analytics platforms (Mixpanel, etc.). **Preferred Qualifications:** • **Background in POS-Integrated SaaS or Industries**: Experience in cannabis, CPG, hospitality, or retail tech. • **Experience Managing CS + Support Hybrid Orgs**: Ability to manage a hybrid CS and support organization. • **Firsthand Experience as a Frontline Worker**: Experience as a budtender, server, retail associate, or similar role. • **Familiarity with CS Forecasting Models and Retention/Churn Analytics Frameworks**: Knowledge of CS forecasting models and retention/churn analytics frameworks. **What We Offer:** • **Competitive Compensation**: $140,000–$160,000 + significant equity package. • **Unlimited PTO + Flexible Work Schedule**: Work from anywhere in the US and enjoy unlimited PTO. • **Health Benefits**: Full medical, dental, and vision coverage. • **Wellness Stipends + Mental Health Resources**: Support for your physical and mental well-being. • **Remote First**: Work from anywhere in the US and enjoy a remote-first work environment. • **Team Retreats**: Company-sponsored gatherings twice a year. • **Ongoing Development**: Resources for personal and professional growth. **Apply Now** If you're a visionary leader with a passion for transforming customer success, we want to hear from you. Apply now to join arenaflex and be part of a revolutionary journey in the retail sector. Apply for this job