Director, Customer Success (Central Region)

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 PowerSchool27s 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 organization27s 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 PowerSchool27s 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

• Knowledge

  • 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, PowerBI tools) and how to leverage data to predict customer behavior at scale

  Skills

  • 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

  Abilities

  • Ability to serve as a trusted strategic advisor to internal executive teams and enterprise customer boards
  • Ability to thrive in ambiguity and lead organizations through rapid periods of hyper-growth or transformation
  • Ability to unite disparate, matrixed functions (Product, Sales, Support, Services) behind common customer outcomes and shared performance goals
  • Ability to travel up to 30% for key moments such as team summits, training, customer meetings, and company events, with increased frequency during peak periods based on business demands.

  Experience & Education

  • Bachelor27s 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 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

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

• 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