Sr. Director - Ai, Innovation and Digital Employee Experience

Expedia Expedia · Hospitality · Washington - Seattle Campus, Austin Domain 11 - HomeAway, USA - Illinois - Chicago, USA - California - San Jose

This role is responsible for defining and driving the AI and automation strategy for the digital employee experience at Expedia Group. The Sr. Director will integrate AI into the flow of work across various platforms (People Technology, Productivity Tools, Endpoints, Identity) to create a unified, low-friction employee experience. Key responsibilities include architecting integrated systems, reimagining team structures for AI adoption, building KPI frameworks for AI-driven gains, and influencing cross-functional stakeholders. The role requires deep technical fluency in LLM integration, enterprise search, workflow automation, and experience with generative AI, virtual assistants, and agentic workflows at enterprise scale.

What you'd actually do

  1. Define and own the holistic digital employee experience vision - connecting People Technology, Productivity Tools, Endpoints, Identity, and AI into a unified, low-friction experience across the entire employee lifecycle (onboarding → daily work → career growth → offboarding).
  2. Define and drive the multi-year AI and automation strategy across Collaboration & Productivity, End User Services, and Corporate IT - embedding AI into the flow of work for leaders, managers, and frontline teams.
  3. Partner with platform, engineering, and People Technology leaders to architect the integrated employee experience layer - ensuring Workday, ServiceNow, Glean, Slack, Zoom, Atlassian, and endpoint platforms work together through coherent APIs, data models, and design patterns.
  4. Reimagine team structures, skills, and operating models to embrace AI as a core capability - not an add-on. Build teams where AI augments every role and where experimentation, learning, and rapid iteration are the norm.
  5. Build KPI frameworks that measure what matters: adoption, time saved, friction eliminated, employee satisfaction, resolution speed, and AI-driven productivity gains.

Skills

Required

  • AI-native
  • driven AI agendas
  • shipped AI-powered products
  • fundamentally changed how organizations work through intelligent technology
  • Think in terms of prompts, agents, workflows, and outcomes
  • 12+ years in technology, product, digital transformation, or AI/ML platform roles
  • ownership of enterprise-scale internal platforms, employee productivity tools, or digital workplace solutions
  • Proven track record leading strategy, design, and delivery of complex, multi-service or enterprise-wide technology initiatives with measurable impact on user experience and business outcomes
  • Deep technical fluency across LLM integration, enterprise search architectures, API design, data modelling, workflow automation, and digital workplace platforms
  • Cross-functional influencer
  • align teams without heavy process
  • influence senior stakeholders
  • bring clarity to complex, multi-stakeholder environments
  • Builder of exceptional teams
  • attract and develop talent that is creative, accountable, AI-fluent, and excited about shaping the future of work

Nice to have

  • Advanced degree in a technical or quantitative field (e.g., computer science, engineering, human-computer interaction, data science) with focus areas relevant to AI, automation, or digital experience
  • Experience operating AI-powered or digital workplace platforms at global scale - including performance, reliability, observability, and continuous improvement of employee-facing services
  • Demonstrated leadership in defining architectural direction and technical standards for AI-enhanced or highly integrated internal tools - ensuring security, compliance, and interoperability across a complex ecosystem
  • Proven ability to use data, experimentation, and insights to priorities investments, optimize employee journeys, and drive adoption and change management for new AI and digital capabilities
  • Familiarity with safely integrating generative AI, virtual assistants, agentic workflows, or intelligent automation into employee experiences at enterprise scale
  • Experience working across People Technology (Workday, ServiceNow), Productivity Tools (Slack, Zoom, Atlassian), and Endpoint Management

What the JD emphasized

  • AI-native
  • shipped AI-powered products
  • agents, workflows, and outcomes
  • LLM integration
  • workflow automation
  • agentic workflows

Other signals

  • Define and drive the multi-year AI and automation strategy
  • embedding AI into the flow of work
  • architect the integrated employee experience layer
  • Reimagine team structures, skills, and operating models to embrace AI as a core capability
  • Build KPI frameworks that measure... AI-driven productivity gains
  • AI-native. You don’t just understand AI - you’ve driven AI agendas, shipped AI-powered products, and fundamentally changed how organizations work through intelligent technology.
  • Think in terms of prompts, agents, workflows, and outcomes.
  • Deep technical fluency across LLM integration, enterprise search architectures, API design, data modelling, workflow automation, and digital workplace platforms
  • Familiarity with safely integrating generative AI, virtual assistants, agentic workflows, or intelligent automation into employee experiences at enterprise scale.