Director, Enterprise Customer Success

10+ years of progressive experience in Customer Success, Account Management, or related roles. Minimum of 3 years managing and mentoring a high-performing team. Proven track record of meeting or exceeding renewal and expansion revenue targets for a book of business exceeding $10MM. Strong commercial instincts with fluency in enterprise buying cycles, value frameworks, and negotiation strategies. Executive presence and ability to communicate complex ideas to C-suite stakeholders. Demonstrated ability to navigate large, matrixed organizations and influence without authority. Willingness to travel regularly to meet with key account stakeholders. Strong operational discipline and demonstrated experience owning revenue forecasting and renewal pipeline management. Experience in K-12 EdTech or broader Enterprise SaaS/technology environments (preferred). Demonstrated experience partnering with RevOps and FP&A to improve forecasting models and renewal playbooks (preferred). Strong analytical skills with comfort in financial modeling, unit economics, and data-driven storytelling (preferred). Familiarity with customer lifecycle tooling (Gainsight, Salesforce, etc.) and integrating these tools with other revenue systems (preferred).

Lead, mentor, and inspire a team of Enterprise Customer Success Managers. Manage team performance against KPIs like GRR/NRR, customer health, and product adoption. Drive professional development of the team. Own enterprise CS capacity planning, including headcount and role design. Scale team processes to support segment growth. Serve as the executive-level point of contact for Enterprise customers. Understand customer business objectives and guide them to maximize value. Build and maintain C-suite relationships. Own executive-level risk escalation and intervention strategies. Stay attuned to enterprise market trends and customer needs. 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. Identify, scope, and pursue upsell/cross-sell opportunities. Partner with Sales on account plans with clear commercial targets. Lead executive business reviews. Establish and own the rigor of the renewal forecasting process. Leverage data-driven insights to forecast account health, renewal risk, and expansion potential. Build scalable processes to improve enterprise engagement, adoption, and maturity. Ensure best-in-class onboarding, value realization, and lifecycle management. Articulate enterprise customer health, priorities, and value narratives to executive stakeholders. Collaborate with Product to represent the voice of the enterprise customer. Work with Marketing and Enablement to communicate success stories. Partner extensively with Finance (FP&A) and RevOps to refine commercial models and improve revenue projection accuracy.