Director, Scaled Customer Success

PowerSchool

Director of Scaled Customer Success overseeing AI-driven engagement and customer success strategies. Responsible for improving retention and product adoption for thousands of customers.

Posted 5/24/2026full-timeDallas • Texas • 🇺🇸 United StatesLead💰 $144,500 - $180,600 per yearWebsite

About the role

Key responsibilities & impact

Transform how we support customers through digital, AI‑driven engagement.
Own strategic initiatives and serve as the architect of an AI‑first engagement engine designed to drive retention and product adoption at scale.
Design and deploy AI-driven playbooks that automate routine success motions, including onboarding, product engagement and adoption, health checks, while maintaining a personalized feel.
Integrate predictive AI models that identify ‘at-risk’ signals before they become churn realities.
Oversee the creation of dynamic, AI-generated campaigns and automated email flows tailored to specific personas and behaviors.
Build end-to-end digital journeys that guide customers from initial implementation to ‘value realization’ without requiring a dedicated CSM.
Lead strategy for in-product messaging and self-service capabilities to resolve queries and drive feature adoption.
Use AI and automation to identify ‘ready-to-buy’ signals, creating automated lead generation paths.
Drive organizational change through training, communication, and stakeholder engagement.
Define KPIs and dashboards to measure success of digital initiatives and customer outcomes, including churn and adoption.

Requirements

What you’ll need

Bachelor’s degree in Business, Technology, or related field
10+ years of experience in Customer Success, Success Transformation, or SaaS operations.
Proven track record of leading technology implementations and process improvements in a SaaS environment driving successful outcomes.
Strong understanding of customer success metrics, lifecycle management, and SaaS business models.
Excellent leadership, communication, and stakeholder management skills.
Experience with technology platforms like Salesforce, Gainsight, or the newest AI-first Customer Success Platforms.
Knowledge of automation, AI-driven customer engagement, and data analytics.
Ability to manage cross-functional projects and influence at all organizational levels.
Background in Educational Technology.
Prior management or team‑lead experience preferred, as this role is expected to evolve into a leadership position with direct reports.

Benefits

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI-driven engagementpredictive AI modelsautomationcustomer success metricslifecycle managementSaaS operationsprocess improvementsdata analyticsdigital journeysKPI definition

Soft Skills

leadershipcommunicationstakeholder managementorganizational change managementinfluenceproject managementtrainingcustomer engagementteam leadershipstrategic thinking