Director of Customer Success

TL;DR:

• Transformational leadership role at a venture-backed SaaS startup (TenOneTen Ventures, Jason Calacanis)
• Fully remote, full benefits package and stock options
• Competitive compensation: $140K–$160K + equity, unlimited PTO, wellness incentives, full health coverage
• A pivotal role owning the evolution of our Customer Success org—from strong foundation to enterprise-grade operation

About SparkPlug SparkPlug is the leading performance platform for frontline retail teams in the cannabis industry, powering real-time incentives, training, content, and analytics. We directly integrate with POS systems to connect brands, retailers, and frontline employees, enabling measurable sales lift and operational excellence. SparkPlug is used 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 hiring a 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. ️ What You’ll Do

• 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
• 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.)

Bonus Points For:

• 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
• Salary Range: $140,000–$160,000 + 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

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