Digital Strategy Director Jobs in Oregon (NOW HIRING)

We're seeking a Director of AI Strategy & Digital Success to transform how we support customers through digital, AIdriven engagement. This role will own strategic initiatives and serve as the architect of an AIfirst 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 directorlevel capability now, even though the role won't include direct reports initially, with leadership responsibilities expanding longterm.

The ideal candidate will show that "low touch" doesn't mean "low value," using generative AI and automation to deliver a seamless, personalized, highimpact experience to thousands of customers at once.

This position is open to both Plano, TX and Austin, TX. 

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.

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 teamlead 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.

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 accomodations@powerschool.com. #LI-TD1 #LI-HYBRID