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

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

2026-52670 Dallas, TX Apply View All Jobs View All Dallas Jobs Overview

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. 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 teamlead experience preferred, as this role is expected to evolve into a leadership position with direct reports.

Compensation & Benefits