Director, Customer Success (Central Region)

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.

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 

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 

• 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 

  • 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 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

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 [email protected].