Director, AI Strategy & Digital Success

🇺🇸Remote - US-TX-Dallas | US-US-Remote$145K–$181K/yr1w ago

K-12 Customer Success AI Strategy Digital Engagement Scaled Customer Success Retention Strategy

Role Snapshot

Director of Scaled Customer Success role to architect an AI-first engagement engine that drives retention and product adoption at scale across thousands of customers. This director-level position operates independently with minimal oversight, with expectations to build a team long-term.

Key Responsibilities: Design and deploy AI-driven playbooks for onboarding, engagement, adoption, and health checks; build end-to-end digital customer journeys; lead in-app orchestration and self-service strategies; identify churn signals and expansion opportunities through predictive analytics; define KPIs and dashboards to measure success of digital initiatives.

Skills & Tools: Expertise in AI/generative AI, customer success strategy, digital transformation, predictive analytics, and automation; strong capabilities in change management, cross-functional collaboration, data-driven decision making, and customer segmentation.

Qualifications: Bachelor's degree in Business, Technology, or related field with proven experience in customer success, digital strategy, or related roles at director or senior management level. Experience with AI tools, customer success platforms, and scaling operations for mid-to-large customer bases required.

Location: Remote - US-TX-Dallas | US-US-Remote

Compensation: $145K–$181K/yr

Prep for this role with AI tools →

Job Description

We’re seeking a Director of Scaled Customer 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.

View Full Job Posting on PowerSchool