Director of Customer Success – Transforming Customer Success at arenaflex

Join arenaflex, a leading venture-backed SaaS startup, as we revolutionize the performance platform for frontline retail teams in the cannabis industry. At arenaflex, we're on a mission to transform how the $20T+ global retail sector collaborates, executes, and rewards performance. Our innovative platform, SparkPlug, powers real-time incentives, training, content, and analytics, directly integrating with POS systems to connect brands, retailers, and frontline employees. With over 3000 businesses in the US using our platform, we're poised for rapid growth and expansion.

About arenaflex

arenaflex is a fast-growing, venture-backed startup with a strong foundation in the cannabis industry. Our investors include TenOneTen Ventures, the creator of Google AdSense, and Jason Calacanis. We're committed to creating a culture of innovation, collaboration, and customer success.

The Role: Director of Customer Success

We're seeking an experienced Director of Customer Success to lead, modernize, and scale our existing Customer Success 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.

Key Responsibilities:

* Lead and elevate a Customer Success team of ~10 (CSMs, support, onboarding specialists) across multiple customer segments

• Redesign and optimize onboarding, engagement, retention, and expansion workflows, with a focus on high-touch, account-based models
• Implement scalable systems and dashboards to improve reporting, performance analytics, account health visibility, and retention forecasting
• Drive tighter alignment between CS and Product by systematizing feedback loops, usage insights, and strategic account input
• Build a robust 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 collaborating with Product, Engineering, and RevOps
• Guide tooling decisions and integrations across Hubspot, Intercom, analytics platforms, and internal admin systems
• Own key outcomes like NRR, time-to-value, onboarding conversion, CSAT, and churn reduction

Essential Qualifications:

* 6–10+ years in Customer Success or Account Management, including 2–4+ years leading and scaling teams in an early stage B2B SaaS company

• Deep experience overhauling CS functions—processes, reporting, playbooks, org structure—not just maintaining
• Proven ability to lead cross-functional initiatives involving Product, Engineering, and Data teams
• Passionate about building systems and structure: internal dashboards, forecasting, segmentation, usage visibility
• Experience supporting high-touch SaaS implementations, preferably with white-glove onboarding for enterprise or mid-market clients
• Confident operating in early-stage, high-growth environments where structure is evolving and velocity is high
• Exceptional written and verbal communicator; clear, precise, and persuasive with stakeholders at all levels
• Tech-savvy: fluent in tools like Hubspot, Intercom, Notion, and product analytics platforms (Mixpanel, etc.)

Preferred Qualifications:

* Background in POS-integrated SaaS or industries like cannabis, CPG, hospitality, or retail tech

• Experience managing CS + Support hybrid orgs
• Firsthand experience as a frontline worker (budtender, server, retail associate)
• Familiarity with CS forecasting models and retention/churn analytics frameworks

What We Offer:

* Competitive compensation: $140K–$160K + significant equity package

• Unlimited PTO + flexible work schedule
• Health Benefits: Full medical, dental, and vision coverage
• Wellness Stipends + mental health resources
• Remote First: Work anywhere in the U.S.
• Team Retreats: Company-sponsored gatherings twice a year
• Ongoing Development: Resources for personal and professional growth

Why arenaflex?

At arenaflex, we're passionate about creating a culture of innovation, collaboration, and customer success. We believe in empowering our employees to grow and develop their skills, and we're committed to making a positive impact in the cannabis industry.

Apply Now:

If you're a seasoned Customer Success leader looking for a new challenge, we encourage you to apply for this exciting opportunity. Join our team and help us transform the performance platform for frontline retail teams in the cannabis industry. [Apply Job!](https://www.areflex.com/careers) [Apply to this Job](https://www.areflex.com/careers/director-of-customer-success) Apply for this job