Job Description

Description

• 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

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

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.)

🌿 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

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

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