[Hiring] Director, Customer Success @PowerSchool Group

Role Description

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

• Strategic Leadership & Value Realization
  • Lead and scale a high-performing, multi-layered organization, including Customer Success Managers and Team Leads/Managers, establishing a culture of proactive value delivery.
  • Transform the organization’s mindset to strategic engagement by embedding disciplined practices around value discovery, alignment with customer strategic priorities, and the execution of adoption and value sustainment plans.
  • Define the overarching framework for customer health and value realization, ensuring customers achieve deep product adoption and operational maturity across the PowerSchool portfolio.
  • Serve as an executive escalation point for high-risk or high-value accounts, orchestrating cross-functional interventions to protect portfolio health.
• Executive Relationship Management & Advocacy
  • Build and maintain peer-level relationships with C-suite and executive sponsors across our most critical customer organizations (e.g., major school district Superintendents, CIOs, and Cabinet leaders).
  • Champion the "Voice of the Customer" at the corporate level, partnering directly with Product and Engineering executives to align PowerSchool’s long-term roadmap with the strategic needs of the market.
  • Lead complex, high-stakes Executive Business Reviews (EBRs) in coordination with Sales leadership to showcase realized ROI and secure long-term alignment.
• Retention Strategy & Revenue Growth
  • Hold ultimate accountability for key SaaS performance metrics, including Gross Retention Rate (GRR), and customer lifetime value across the assigned portfolio.
  • Co-architect the joint GTM strategy with Sales leadership, ensuring seamless execution of renewal strategies and early identification of expansion/whitespace opportunities.
  • Establish institutionalized tracking of SaaS adoption and utilization metrics, translating low-usage trends into proactive risk mitigation playbooks.
  • Drive robust forecasting accuracy and portfolio predictability, leading regular operational reviews with executive leadership.
• Operational Excellence & Scaling
  • Design, build, and optimize customer engagement models, including tier segmentation, digital-touch success strategies, and customer lifecycle playbooks.
  • Inject high operational rigor into the organization, optimizing CRM and Customer Success Platform (CSP) hygiene, success planning frameworks, and executive dashboards to drive data-backed decision-making.
  • Collaborate deeply with Professional Services, Support, Finance, and Product to remove friction from the customer experience and streamline cross-functional workflows.
• Leadership & Talent Development
  • Attract, develop, and inspire a world-class Customer Success team, building continuous coaching frameworks for both frontline individual contributors and people managers.
  • Drive modern organizational design and change management initiatives to support scale, organizational maturity, and career progression within the Customer Success branch.
  • Foster a transparent, high-accountability culture focused on customer outcomes, professional development, and collaborative innovation.

Qualifications

• Mastery of enterprise SaaS Customer Success methodologies, specifically value discovery frameworks, strategic alignment, health-scoring structures, and long-term customer lifecycle management.
• Deep financial acumen regarding SaaS economics, with an expert understanding of how customer health metrics directly influence NRR, GRR, and LTV.
• Expertise in managing large, matrixed, multi-layered organizational structures and directing complex change-management initiatives.
• Advanced knowledge of modern CS technology stacks (e.g., Salesforce, Statisfy, Certinia, Power BI tools) and how to leverage data to predict customer behavior at scale.
• Polished executive presence and communication skills, with a proven ability to challenge, influence, and build consensus among senior internal executives and enterprise clients.
• Superior analytical capabilities, with the skill to synthesize complex SaaS utilization metrics and customer sentiment into broad, actionable corporate strategies.
• Strong commercial and negotiation orientation, with the ability to navigate complex contractual, renewal, and risk mitigation environments seamlessly.

Requirements

• Bachelor’s degree; MBA or advanced degree preferred.
• 10+ years of experience in Customer Success, Strategic Account Management, GTM Leadership, or Management Consulting within SaaS or technology organizations.
• 5+ years of direct people management experience, with at least 3+ years managing other people managers or leading a large, multi-tiered team.
• Proven track record managing large strategic portfolios with significant revenue ownership (typically $100M+ ARR).
• Experience in K-12 education technology, or the public sector, is a plus.

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.