Director, AI Strategy & Digital Success (Plano/Austin)

We’re seeking a Director of AI Strategy & Digital Success to transform how we support customers through digital, AI-driven engagement. This role will own strategic initiatives and serve as the architect of an AI-first engagement engine designed to drive retention and product adoption at scale. We need someone who can operate independently from day one and perform at a high level with minimal oversight, with the expectation that a team will be built under them over time. We’re targeting director-level capability now, even though the role won’t include direct reports initially, with leadership responsibilities expanding long-term. The ideal candidate will show that “low touch” doesn’t mean “low value,” using generative AI and automation to deliver a seamless, personalized, high-impact experience to thousands of customers at once. This position is open to both Plano, TX and Austin, TX. Responsibilities Digital strategy and implementation

• Scale the human touch: design and deploy AI-driven playbooks that automate routine success motions, including onboarding, product engagement and adoption, health checks, while maintaining a personalized feel
• Predictive churn modeling: integrate predictive AI models that identify ‘at-risk’ signals before they become churn realities.
• GenAI content engine: partner with the success team to oversee the creation of dynamic, AI-generated campaigns and automated email flows tailored to specific personas and behaviors.

Scaled engagement operations

• Digital journey mapping: build end-to-end digital journeys that guide customers from initial implementation to ‘value realization’ without requiring a dedicated CSM.
• In-App orchestration: lead strategy for in-product messaging and self-service capabilities to resolve queries and drive feature adoption.
• Partner with IT and Product teams to ensure seamless deployment and adoption of the Customer Success platform.

Revenue & retention accountability

• Expansion mapping: use AI and automation to identify ‘ready-to-buy’ signals, creating automated lead generation paths.

Change Management & Enablement

• Drive organizational change through training, communication, and stakeholder engagement.
• Foster a culture of continuous improvement and innovation.

Analytics & Reporting

• Define KPIs and dashboards to measure success of digital initiatives and customer outcomes, including churn and adoption.
• Segment customers by risk, maturity, persona, and behavior.
• Provide insights into leadership on trends, risks, and opportunities for improvement.
• Use data to identify systemic churn drivers and design scalable interventions to support key elements of retention strategy, particularly in mid-low market customers.

Partner with the cross-functional team to:

• Track engagement and usage signals
• Measure impact of digital programs on retention.

• Experience with technology platforms like Salesforce, Gainsight, or the newest AI-first Customer Success Platforms.
• 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.

Preferred Skills

• 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.

Compensation & Benefits Compensation & Benefits 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

A reasonable estimate of the base compensation range for this position is $144,500 - $180,600 USD. This compensation range is specific to the United States and it incorporates many factors including but not limited to an applicant’s skills and prior relevant experience and training; licensures, degrees, and certifications; internal equity; internal pay ranges; and market data/range parameters. EEO Commitment EEO Commitment

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