[Hiring] Director, Customer Success Operations @PowerSchool Group LLC

Role Description

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.

Qualifications

• 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
• Hands-on experience with a CSP and Salesforce ecosystems (Preferred)
• Experience building retention models and predictive health scoring frameworks (Preferred)
• Strong background in digital customer success and scaled engagement models (Preferred)
• Experience leading transformation initiatives (automation, AI, or operating model shifts) (Preferred)

Requirements

• 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
• 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
• 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
• 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
• 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
• 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
• 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

Benefits

• Comprehensive Insurance Coverage (including Medical, Dental, Vision, Pharmacy benefits, Life Insurance and AD&D)
• Flexible Spending Accounts and Health Savings Accounts
• Short-Term Disability and Long-Term Disability
• Comprehensive 401(k) plan
• Generous Parental Leave
• Unrestricted paid time off (known as Discretionary Time Off - DTO)
• Wellness Program, including ClassPass & Employee Assistance Program
• Tuition Reimbursement
• Optional Benefits: Pet Insurance, Identity Theft Protection, Student Debt Repayment Program and Prepaid Legal coverage