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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Director of AI Strategy & Digital Success - **Company:** POWER SCHOOL GROUP LLC - **Location:** Austin, TX, United States (Remote available) - **Experience:** Expert - **Salary:** $145,000.0 - $181,000.0 - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Data Analysis, Software as a Service, Salesforce.Com, Data Analytics - **Published:** September 24, 2026 - **Apply:** https://www.builtincolorado.com/job/director-ai-strategy-digital-success-plano-austin/11340473?handler=ApplyRedirect ## 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., Leads business development and capture activities for Latin American defense and government customers. Identifies opportunities, analyzes customer and competitor needs, builds senior stakeholder relationships, coordinates bids and proposals, shapes requirements, manages campaign plans, and supports trade shows and customer engagements. Requires extensive aerospace or defense experience, regional customer expertise, cross-cultural fluency, knowledge of U.S. and international defense sales frameworks, export controls, local partnerships, and English proficiency; Spanish and Portuguese are preferred. Top Skills: CRMDirect Commercial Sales (Dcs)EarForeign Military Sales (Fms)ItarPipeline Management ToolsUncrewed Air Systems ## 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., 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 in Leadership: How Technology is Reshaping Executive Roles](https://www.wearedevelopers.com/videos/1705-ai-in-leadership-how-technology-is-reshaping-executive-roles) - [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) - [From Global Capability Centers to AI-Powered Command Centers](https://www.wearedevelopers.com/videos/100096-from-global-capability-centers-to-ai-powered-command-centers) ## Related Articles - [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) - [How to Become an AI Engineer](https://www.wearedevelopers.com/magazine/331-how-to-become-an-ai-engineer) - [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) - [Navigating the AI Shift](https://www.wearedevelopers.com/magazine/629-navigating-the-ai-shift) - [Got AI ideas but no money? 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