Director of Customer Success

Summary

Join SparkPlug, a leading performance platform for frontline retail teams in the cannabis industry, as their Director of Customer Success. This is a fully remote, transformational leadership role offering a competitive compensation package ($140K–$160K + equity), unlimited PTO, and full benefits. You will lead a team of 10+ experienced CSMs and support specialists, modernizing and scaling the existing Customer Success organization. The role involves a comprehensive overhaul of the customer journey, onboarding, processes, tooling, and analytics infrastructure. You will drive improved cross-functional alignment and build a high-performing, data-informed CS function. This is a strategic leadership role with high autonomy and executive support.

Requirements

• 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.)

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

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

Benefits

• 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