Director, Strategic Customer Success

PowerSchool; Chicago (IL); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

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

Job summary

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.

Qualifications

• 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.

Responsibilities

• 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.

Skills

Executive-level communication

Leadership

Analytical thinking

SaaS / Customer Success

Education

Bachelor’s degree

MBA or advanced degree

Tools

Salesforce

Power BI

Certinia

Statisfy

Job description

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.