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.
ResponsibilitiesDigital 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.
Minimum Qualifications
- 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.
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 CommitmentEEO CommitmentPowerSchool 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]. #LI-TD1 #LI-HYBRID
Skills Required
- Experience with technology platforms such as Salesforce, Gainsight, or AI-first Customer Success Platforms
- 10+ years of experience in Customer Success, Success Transformation, or SaaS operations
- Proven track record leading technology implementations and process improvements in a SaaS environment
- Strong understanding of customer success metrics, lifecycle management, and SaaS business models
- Excellent leadership, communication, and stakeholder management 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
Powerschool Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Powerschool and has not been reviewed or approved by Powerschool.
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Healthcare Strength — Health coverage includes medical, dental, and vision with an HSA option and company HSA match, plus life insurance and short/long‑term disability. Wellness resources such as an Employee Assistance Program and ClassPass are also part of the package.
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Retirement Support — A 401(k) with company match is offered and highlighted across company materials and job postings. Vesting on the match is described as not immediate.
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Leave & Time Off Breadth — Discretionary Time Off (unlimited PTO) for many U.S. roles and paid holidays are emphasized, with recent postings confirming the DTO approach. Paid parental leave is also cited in company materials.
Powerschool Insights
What We Do
PowerSchool is a leading provider of cloud-based software for K-12 education in North America. Its mission is to empower educators, administrators, and families to ensure personalized education for every student journey. PowerSchool offers end-to-end product clouds that connect the central office to the classroom to the home with award-winning products including Schoology Learning and Naviance CCLR, so school districts can securely manage student data, enrollment, attendance, grades, instruction, assessments, human resources, talent, professional development, special education, data analytics and insights, communications, and college and career readiness. PowerSchool supports over 60 million students in more than 90 countries and over 18,000 customers, including more than 90 of the top 100 districts by student enrollment in the United States.
