Director of Customer Success Operations, PowerSchool

• 8+ years of experience in Customer Success, Operations, Revenue Operations, or related function
• 3+ years of people leadership experience
• Proven success scaling operations in a SaaS or technology-enabled environment
• Strong analytical skills with demonstrated ability to translate data into action
• Deep experience driving cross-functional initiatives and organizational change

Desirable

• The Director, Customer Success Operations is a strategic transformation leader responsible for building and scaling the operating engine that drives customer health, retention, and expansion
• Reporting to the VP of Customer Success Operations, this role translates Customer Success strategy into disciplined execution by designing scalable processes, enabling data-driven decision-making, and embedding operational rigor across the organization
• This leader plays a critical role in advancing the organization toward a predictive, digital-first Customer Success model, with direct ownership of the retention framework, scaled/digital engagement motions, and implementation and optimization of a new Customer Success platform
• Success in this role is measured by improvements in retention outcomes, forecast accuracy, operational efficiency, and the ability to scale Customer Success without linear cost growth
• Retention Model Ownership (Core Priority)
• Own the design, evolution, and operationalization of the Customer Success retention model
• Define and standardize key drivers of retention, including customer health scoring, risk identification and value sustainment
• Improve predictability of churn and renewal outcomes through data, insights, and process discipline
• Partner with GVP of Customer Success to embed proactive, outcomes-driven behaviors across the organization
• Establish governance and operating rhythms (risk reviews, forecast calls, value alignment) tied to retention performance
• Digital & Scaled Customer Success Motions
• Lead the shift toward digital-first and scaled engagement models to improve coverage, efficiency, and consistency
• Evaluate segmentation, coverage models, and lifecycle journeys across high-touch, tech-touch, and digital segments
• Design and implement automated customer journeys, campaigns, and lifecycle orchestration
• Increase adoption of digital programs while maintaining strong customer experience and outcomes
• Partner with Marketing, Product, and Enablement to deliver cohesive digital customer experiences
• Customer Success Platform (CSP) Deployment, Optimization & CS Technology Strategy
• Own deployment of a new CSP as the system of action for Customer Success
• Standardize playbooks, CTAs, health scoring, and workflows to drive consistency and scale
• Improve data integrity, usability, and adoption across CS teams
• Partner with Data, IT, and Sales Operations to align CRM (Salesforce) and CSP data models
• Lead the roadmap for automation, AI-driven insights, and predictive analytics within the CSP
• Operating Model & Process Transformation
• Define and evolve the Customer Success operating model (segmentation, lifecycle governance, engagement motions)
• Translate CS strategy into scalable processes and programs across onboarding, adoption, risk, renewal, and escalation
• Drive standardization while enabling flexibility for different customer segments
• Lead enterprise-wide change management to drive adoption of new processes and operating models
• Insights, Forecasting & Performance Management
• Develop and maintain executive dashboards and KPIs for customer health, retention, and operational performance
• Improve renewal forecast accuracy through better data, processes, and accountability
• Lead capacity planning, coverage modeling, and cost-to-serve optimization
• Deliver actionable insights to identify trends, risks, and growth opportunities across the customer base
• Cross-Functional Leadership & Governance
• Act as a strategic partner to Customer Success, Product, Sales, Support, Finance, and Enablement teams
• Drive alignment on customer lifecycle ownership, handoffs, and shared outcomes
• Establish and lead operating cadences (business reviews, risk reviews, exec reporting)
• Advocate for customer needs and operational improvements across the organization
• Team Leadership & Capability Building
• Build and lead a high-performing Customer Success Operations team
• Define clear roles across operations, analytics, systems, and program management
• Develop talent, coaching leaders in operational excellence and data-driven execution
• Foster a culture of accountability, continuous improvement, and customer-centric thinking
• Key Performance Indicators (KPIs)
• Retention & Customer Outcomes
• Gross and Net Revenue Retention (GRR / NRR)
• Health score accuracy (predictive vs. actual outcomes)
• Time-to-value and product adoption metrics
• Reduction in escalations and churn drivers
• Operational Excellence
• Forecast accuracy (retention and risk)
• Process consistency and adherence
• Gainsight/CSP adoption and data quality
• Cycle time reduction across CS workflows
• Scale & Efficiency
• Cost-to-serve improvements
• Expansion of digital/scaled coverage
• Automation adoption and workflow efficiency
• Cross-functional SLA performance
• What Success Looks Like
• A predictive, trusted retention and customer health engine is in place and used consistently by CS leadership
• CSP is fully leveraged as a system of action, not just reporting
• Digital CS motions are scaled and delivering measurable improvements in coverage and efficiency
• Customer Success teams operate with clarity, consistency, and accountability
• Leadership has real-time visibility into customer health and operational performance
• Retention, expansion, and customer outcomes improve at scale without proportional cost increase