Job description
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
