Customer Success Operations Jobs in Wisconsin (NOW HIRING)

About PowerSchool

At PowerSchool, we power education for students around the world. As the global leader in cloud-based K-12 software, we support the full education ecosystem—from the central office to the classroom to the home. Joining PowerSchool means being part of a mission-driven team that is transforming K-12 education by helping schools operate more effectively and deliver better outcomes for educators, students, and families.

Our Success team ensures our partners in educational technology achieve their desired outcomes, serving as champions of our customers' needs. Through collaboration, strong relationships, and advocacy, the Success team positively impacts customer retention through proactive engagement and delivering excellence to our customers.

Director, Customer Success Operations

Role Overview

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.

Key Responsibilities

• 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

Qualifications

Required

• 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

Preferred

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

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 workflowsCost-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

PowerSchool offers the following 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
• 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

A reasonable estimate of the base compensation range for this position is $55,700 - $172,400 USD. This compensation range is specific to the United States and it incorporates many factors including but not limited to an applicant's skills and prior relevant experience and training; licensures, degrees, and certifications; internal equity; internal pay ranges; and market data/range parameters.

PowerSchool is committed to a diverse and inclusive workplace. PowerSchool is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status. Our inclusive culture empowers PowerSchoolers to deliver the best results for our customers. We not only celebrate the diversity of our workforce, we celebrate the diverse ways we work. If you have a disability and need an accommodation regarding our recruiting process, please let us know by emailing accomodations@powerschool.com.