Director, Enterprise Customer Success

We are seeking a seasoned Enterprise Customer Success Director who combines world-class customer management expertise with strong commercial acumen. This role will lead a team of Enterprise Customer Success Managers (CSMs) and own the retention and growth of our most strategic, $20MM+ Enterprise segment. You will be responsible for driving long-term value creation across our largest and most complex customers (e.g., districts with 20,000+ students). You will partner closely with Sales, Product, and Executive Leadership to ensure our enterprise clients achieve measurable outcomes while identifying and executing on growth opportunities.

In this role, you will:

Team Leadership & Development

• Lead, mentor, and inspire a team of high-performing Enterprise Customer Success Managers, fostering a culture of accountability, data-driven decision-making, and excellence.
• Manage team performance against key performance indicators (KPIs) such as Gross/Net Revenue Retention (GRR/NRR), customer health scores, and product adoption metrics.
• Drive the professional development of the team, coaching CSMs on executive engagement, complex negotiation, and strategic account planning.
• Own enterprise CS capacity planning, including headcount planning, role design, and coverage models to support segment growth and retention goals.
• Scale the team's processes and capacity to support future growth in the Enterprise segment.

Customer Leadership & Strategic Management

• Serve as the executive-level point of contact for Enterprise customers, shaping long-term partnership strategies.
• Understand customers’ business objectives deeply and proactively guide them toward maximizing value from our solutions.
• Build and maintain trusted C-suite relationships to influence roadmaps, align on strategic priorities, and ensure renewal stability.
• Own executive-level risk escalation and intervention strategies for at-risk enterprise accounts, partnering with internal leadership to stabilize and retain key customers.
• Stay closely attuned to enterprise market trends and evolving customer needs, translating insights into expansion strategy, account planning, and Product feedback.

Commercial Ownership & Growth

• Own the Enterprise book of business for renewals and expansion; deliver against gross and net revenue retention targets.
• Set and drive the enterprise renewal strategy, ensuring early risk identification, clear deal paths, and disciplined execution across the team.
• Identify, scope, and pursue upsell/cross-sell opportunities based on customer needs, market trends, and product capabilities.
• Partner with Sales on the co-creation of account plans with clear commercial targets and growth paths.
• Lead executive business reviews that drive strategic alignment and unlock new revenue cycles.

Operational Excellence

• Establish and own the rigor of the renewal forecasting process for the Enterprise segment, providing reliable revenue projections to Finance (FP&A) and Sales Leadership.
• Leverage data-driven insights to forecast account health, renewal risk, and expansion potential with high accuracy.
• Build scalable processes that improve enterprise engagement, adoption, and maturity while minimizing churn drivers.
• Ensure best-in-class onboarding, value realization, and lifecycle management for enterprise customers by leveraging customer lifecycle tooling and data.

Cross-Functional Influence

• Clearly articulate enterprise customer health, priorities, and value narratives to executive stakeholders, informing go-to-market and product decisions.
• Collaborate with Product to represent the voice of the enterprise customer and influence roadmap priorities.
• Work with Marketing and Enablement to document and communicate enterprise success stories, proven value drivers, and use cases.
• Partner extensively with Finance (FP&A) and RevOps to refine commercial models, renewal playbooks, and improve revenue projection accuracy.

Why you're a great fit:

Required Qualifications