Director, Customer Success (Central Region)

PowerSchool; Chicago (IL); Presencial; USD 180.000 - 240.000; Jornada completa

Ventajas ofrecidas por este puesto de trabajo

Comprehensive Insurance Coverage

Flexible Spending Accounts and Health

Short-Term Disability and Long-Term

Discretionary Time Off

Wellness Program

Tuition Reimbursement

Pet Insurance

Identity Theft Protection

Student Debt Repayment Program

Prepaid Legal coverage

Descripción de la vacante

PowerSchool is seeking a Director of Customer Success to lead a multi-layered team, driving retention, adoption, and value realization across its largest portfolios. This leader will partner with Sales, Support, Product, and Executive Leadership to maximize ARR.

You will build scalable operating models, own GRR/NRR metrics, recruit and develop talent, and travel up to 30% for customer meetings and events.

Formación

• Executive-level communication and relationship-building with C-suite customers and internal stakeholders.
• Proven ability to lead large, multi-layered organizations and manage change.
• Deep expertise in enterprise SaaS Customer Success, including retention, health, and renewals.

Responsabilidades

• Lead and scale a multi-layered Customer Success organization with accountability and strategic partnerships.
• Define and execute CS strategy for largest portfolios, driving retention, adoption, health, and growth.
• Build executive relationships with key customer stakeholders and act as escalation point for high-value accounts.
• Own SaaS performance outcomes: GRR, LTV, adoption, portfolio health, renewal readiness.
• Partner with Sales to develop retention and growth strategies and deliver Executive Business Reviews.
• Champion the Voice of the Customer to influence priorities across Product, Engineering, Support, and Services.
• Establish scalable CS operating models, including segmentation, lifecycle playbooks, success planning, health scoring, dashboards, and proactive risk management.
• Leverage Salesforce and CS platforms to identify trends and improve portfolio predictability.
• Recruit, coach, and develop CS talent and evolve organizational structure for scale.

Conocimientos

Executive-level communication

Leadership

Analytical thinking

SaaS / Customer Success

Educación

Bachelor’s degree

MBA or advanced degree

Herramientas

Salesforce

Power BI

Certinia

Statisfy

Descripción del empleo

At PowerSchool, we are a dedicated team of innovators guided by our shared purpose of powering education for students around the world. From the central office to the classroom and to the home, PowerSchool supports the entire educational ecosystem as the global leader of cloud-based software for K-12 education. Our employees make it all possible, and a career with us means you are joining a successful team committed to engaging, empowering, and improving the K-12 education experience everywhere.

Team Overview

Our Customer Success organization ensures our customers achieve measurable outcomes through strategic partnership, operational excellence, and customer advocacy. The team plays a critical role in driving customer retention, adoption, health, executive engagement, and long-term growth by delivering value across the customer lifecycle.

Position Summary

The Director, Customer Success is a high-impact leadership role responsible for defining and executing the customer retention, adoption, and value realization strategy across PowerSchool’s largest, highest-value strategic portfolios. This leader will oversee a multi-layered organization of Customer Success Managers and People Managers, shifting the organization from a reactive stance to a proactive, value-driven customer success model. As a key member of the Go-to-Market (GTM) leadership team, the Director partners cross-functionally with Sales, Support, Services, Product, and Executive Leadership to ensure our highest-tier customers realize maximum return on their investment. This role requires an accomplished SaaS executive with deep operational rigor, outstanding business acumen, and a proven track record of scaling teams to protect and grow hundreds of millions in Annual Recurring Revenue (ARR).

Responsibilities

• Lead and scale a high-performing, multi-layered Customer Success organization, developing both Customer Success Managers and people leaders while building a culture of accountability, strategic partnership, and measurable customer value.
• Define and execute the Customer Success strategy for PowerSchool’s largest strategic portfolios, driving customer retention, adoption, health, value realization, and long-term growth.
• Build executive relationships with key customer stakeholders, serving as a trusted advisor and executive escalation point for high-value or at-risk accounts.
• Own key SaaS performance outcomes, including Gross Retention Rate (GRR), customer lifetime value, adoption, utilization, portfolio health, forecasting, and renewal readiness.
• Partner with Sales to develop retention and growth strategies, identify expansion opportunities, and deliver strategic Executive Business Reviews that demonstrate customer outcomes and ROI.
• Champion the Voice of the Customer, partnering with Product, Engineering, Support, Services, and other teams to influence priorities and improve the end-to-end customer experience.
• Establish scalable Customer Success operating models, including customer segmentation, lifecycle playbooks, success planning, health scoring, executive dashboards, and proactive risk-management practices.
• Leverage Salesforce, Customer Success platforms, and customer data to identify trends, improve portfolio predictability, and drive informed decision-making.
• Recruit, coach, and develop Customer Success talent while evolving the organizational structure and processes needed to support continued scale and transformation.

Qualifications

• Deep expertise in enterprise SaaS Customer Success, including value realization, customer health, adoption, retention, renewals, and strategic account management.
• Strong understanding of SaaS economics and performance measures, including NRR, GRR, LTV, adoption, utilization, and revenue retention.
• Proven ability to lead large, multi-layered organizations and successfully manage organizational change and transformation.
• Executive-level communication and relationship-building skills with the ability to influence C-suite customers and senior internal stakeholders.
• Strong analytical and commercial acumen, with experience translating customer, product, and financial data into actionable strategies.
• Experience working across Sales, Product, Support, Services, and other matrixed teams to drive shared customer and business outcomes.
• Experience with modern Customer Success and analytics platforms such as Salesforce, Statisfy, Certinia, and Power BI.
• Ability to travel up to 30% for customer meetings, team events, training, and other key business needs.

Experience & Education

• Bachelor’s degree required; MBA or advanced degree preferred.
• 10+ years of experience in Customer Success, Strategic Account Management, GTM Leadership, or Management Consulting within SaaS or technology.
• 5+ years of people management experience, including 3+ years leading people managers or a large, multi-tiered organization.
• Proven experience managing large strategic customer portfolios with significant revenue responsibility, typically $100M+ ARR.
• K-12 education technology or public-sector experience is a plus

Along with our highly market competitive base compensation, 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

EEO Commitment

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 [e-mail].