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Senior Manager, Enterprise Customer Success

dutchie - Remote - Remote - posted 2026-07-20

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Dutchie is a comprehensive technology platform powering dispensary operations and cannabis commerce across 40+ markets in the US and Canada. Founded in 2017, the company has raised over $600M from top-tier investors including D1 Capital Partners, Tiger Global, and Dragoneer, and is recognized as the leading technology company in the cannabis space. As Senior Manager of Enterprise Customer Success, you will lead and scale a high-performing team of Enterprise Customer Success Managers (CSMs) focused on Dutchie's highest-impact retail and cannabis commerce partners. This is a strategic operational role requiring both people leadership and process architecture expertise. Key responsibilities include: Team Leadership: Coach and mentor a team of enterprise CSMs, identifying best practices from top performers and codifying them into standardized playbooks. Train the team in executive-level presentation skills, strategic selling, and navigating complex multi-stakeholder environments. Process Design & Operational Excellence: Build and implement scalable customer success processes from the ground up. Establish a rigorous Quarterly Business Review (QBR) operating cadence that demonstrates clear ROI. Define and monitor comprehensive customer health metrics, moving beyond lagging indicators to identify early warning signs of churn. Implement disciplined account mapping and proactive risk mitigation protocols. Cross-Functional Collaboration: Partner with Sales leadership to ensure seamless handoffs and coordinated account management. Identify and execute account expansion and cross-sell opportunities across Dutchie's technology suite. Synthesize enterprise trends and product feedback into actionable insights for Product and UX teams. You bring 8+ years of B2B SaaS experience in customer success, account management, or strategic consulting, with 3+ years directly managing enterprise-level CS teams. You have a proven track record designing and launching new operational processes with strict team adoption. You're skilled in establishing customer health scoring systems and using data analytics to forecast churn. You've managed multi-million dollar ARR books and have team members who previously managed $500k+ ARR accounts. You are hyper-organized, detail-oriented, thrive in fast-paced environments, and excel at execution. You're a strategic thinker who can map enterprise accounts to drive massive value and turn complex retail operations into thriving, high-revenue partnerships.

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