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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Director, AI Strategy & Digital Success (Plano/Austin) - **Company:** PowerSchool - **Location:** Plano, TX, United States - **Experience:** Expert - **Salary:** $144,500.0 - $180,600.0 - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Data Analysis, Software as a Service, Salesforce.Com, Data Analytics - **Published:** September 25, 2026 - **Apply:** https://www.careerjet.com/job/us2022581a79c03ac517f48cc3e1017c35/eaa ## About the Role * 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. ## Description 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. ## Related Videos - [AI PowerPlay: Building High-Impact Teams & Transformative Solutions](https://www.wearedevelopers.com/videos/1005-ai-powerplay-building-high-impact-teams-transformative-solutions) - [Data Science in Retail](https://www.wearedevelopers.com/videos/586-data-science-in-retail) - [PySpark - Combining Machine Learning & Big Data](https://www.wearedevelopers.com/videos/44-pyspark-combining-machine-learning-big-data) - [Data Science on Software Data](https://www.wearedevelopers.com/videos/162-data-science-on-software-data) - [How Data is Shaping our Games](https://www.wearedevelopers.com/videos/176-how-data-is-shaping-our-games) - [AI in Leadership: How Technology is Reshaping Executive Roles](https://www.wearedevelopers.com/videos/1705-ai-in-leadership-how-technology-is-reshaping-executive-roles) ## Related Articles - [How to Become an AI Engineer](https://www.wearedevelopers.com/magazine/331-how-to-become-an-ai-engineer) - [Navigating the AI Shift](https://www.wearedevelopers.com/magazine/629-navigating-the-ai-shift) - [Stephan Gillich - Bringing AI Everywhere](https://www.wearedevelopers.com/magazine/489-stephan-gillich-bringing-ai-everywhere) - [What Industries Outside of AI Are Hiring The Most AI Experts?](https://www.wearedevelopers.com/magazine/98-what-industries-outside-of-ai-are-hiring-the-most-ai-experts) - [Coffee with Developers - Maria Apazoglou - Making AI understandable for all in production](https://www.wearedevelopers.com/magazine/475-coffee-with-developers-maria-apazoglou-making-ai-understandable-for-all-in-production) - [Got AI ideas but no money? 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