Sr. Director - AI, Innovation and Digital Employee Experience

Expedia Group•Seattle, WA

About The Position

Expedia Group brands power global travel for everyone, everywhere. We design cutting-edge tech to make travel smoother and more memorable, and we create groundbreaking solutions for our partners. Our diverse, vibrant, and welcoming community is essential in driving our success. Why Join Us? To shape the future of travel, people must come first. Guided by our Values and Leadership Agreements, we foster an open culture where everyone belongs, differences are celebrated and know that when one of us wins, we all win. We provide a full benefits package, including exciting travel perks, generous time-off, parental leave, a flexible work model (with some pretty cool offices), and career development resources, all to fuel our employees' passion for travel and ensure a rewarding career journey. We’re building a more open world. Join us. Expedia Group powers travel for everyone, everywhere. As AI becomes core to how travelers plan, book, and manage their trips, our ability to rapidly explore, prototype, and ship new AI capabilities becomes essential. You will help build the next generation of AI-powered experiences and the underlying patterns that ensure every experience meets a high standard of clarity, accuracy, and trust. Expedia Product & Technology builds innovative products, services, and tools to deliver high-quality experiences for travelers, partners, and our employees. A singular technology platform powered by data and machine learning provides secure, differentiated, and personalized experiences for the traveler and our partners that drive loyalty and customer satisfaction. Our Enterprise IT organization is on a mission to create a frictionless, inspiring technology experience so every Expedian can do their best work, anywhere. We don’t think of IT as a back-office function. We think of it as the connective tissue of the employee experience - the place where People Technology, Productivity & Collaboration Tools, Endpoint Management, Identity, and AI-powered services come together into a single, coherent, delightful experience. When these domains work in harmony, employees spend less time on friction and more time on the work that matters: serving travelers, building the marketplace, and advancing company priorities. In this role, you will: 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). 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. 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. 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. Build KPI frameworks that measure what matters: adoption, time saved, friction eliminated, employee satisfaction, resolution speed, and AI-driven productivity gains. Serve as the connective leader across IT, People Technology, HR, Finance, Workplace, Security, and Engineering - aligning priorities, investments, and governance for AI-driven and digital employee experience programs.

Requirements

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. You think in terms of prompts, agents, workflows, and outcomes.
12+ years in technology, product, digital transformation, or AI/ML platform roles - including 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 - you keep one hand in the technology while building strong teams around it.
Cross-functional influencer. You align teams without heavy process, influence senior stakeholders, and bring clarity to complex, multi-stakeholder environments.
Builder of exceptional teams. You attract and develop talent that is creative, accountable, AI-fluent, and excited about shaping the future of work.

Nice To Haves

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 suites (M365/Google), Collaboration (Slack, Zoom, Atlassian), and Endpoint Management - understanding how these domains interconnect to form the employee experience.

Responsibilities

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).
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.
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.
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.
Build KPI frameworks that measure what matters: adoption, time saved, friction eliminated, employee satisfaction, resolution speed, and AI-driven productivity gains.
Serve as the connective leader across IT, People Technology, HR, Finance, Workplace, Security, and Engineering - aligning priorities, investments, and governance for AI-driven and digital employee experience programs.

Benefits

full benefits package, including exciting travel perks, generous time-off, parental leave, a flexible work model (with some pretty cool offices), and career development resources
medical/dental/vision
paid time off
Employee Assistance Program
wellness & travel reimbursement
travel discounts
International Airlines Travel Agent (IATAN) membership

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