Sr. Director - AI, Innovation and Digital Employee Experience

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. 

Minimum Qualifications:

• 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. 

Preferred Qualifications:

• 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. 

The total cash range for this position in Seattle is $244,500.00 to $342,000.00. Employees in this role have the potential to increase their pay up to $391,000.00, which is the top of the range, based on ongoing, demonstrated, and sustained performance in the role.

The total cash range for this position in Chicago is $232,500.00 to $325,500.00. Employees in this role have the potential to increase their pay up to $372,000.00, which is the top of the range, based on ongoing, demonstrated, and sustained performance in the role. The total cash range for this position in Austin is $244,500.00 to $342,000.00. Employees in this role have the potential to increase their pay up to $391,000.00, which is the top of the range, based on ongoing, demonstrated, and sustained performance in the role. The total cash range for this position in San Jose is to . Employees in this role have the potential to increase their pay up to , which is the top of the range, based on ongoing, demonstrated, and sustained performance in the role.

Starting pay for this role will vary based on multiple factors, including location, available budget, and an individual’s knowledge, skills, and experience. Pay ranges may be modified in the future.

Expedia Group is proud to offer a wide range of benefits to support employees and their families, including medical/dental/vision, paid time off, and an Employee Assistance Program. To fuel each employee’s passion for travel, we offer a wellness & travel reimbursement, travel discounts, and an International Airlines Travel Agent (IATAN) membership. View our full list of benefits.

Accommodation requests

If you need assistance with any part of the application or recruiting process due to a disability, or other physical or mental health conditions, please reach out to our Recruiting Accommodations Team through the Accommodation Request.

We are proud to be named as a Best Place to Work on Glassdoor in 2024 and be recognized for award-winning culture by organizations like Forbes, TIME, Disability:IN, and others.

Expedia Group's family of brands includes: Brand Expedia®, Hotels.com®, Expedia® Partner Solutions, Vrbo®, trivago®, Orbitz®, Travelocity®, Hotwire®, Wotif®, ebookers®, CheapTickets®, Expedia Group™ Media Solutions, Expedia Local Expert®, CarRentals.com™, and Expedia Cruises™. © 2024 Expedia, Inc. All rights reserved. Trademarks and logos are the property of their respective owners. CST: 2029030-50

Employment opportunities and job offers at Expedia Group will always come from Expedia Group’s Talent Acquisition and hiring teams. Never provide sensitive, personal information to someone unless you’re confident who the recipient is. Expedia Group does not extend job offers via email or any other messaging tools to individuals with whom we have not made prior contact. Our email domain is @expediagroup.com. The official website to find and apply for job openings at Expedia Group is careers.expediagroup.com/jobs.

Expedia is committed to creating an inclusive work environment with a diverse workforce. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. This employer participates in E-Verify. The employer will provide the Social Security Administration (SSA) and, if necessary, the Department of Homeland Security (DHS) with information from each new employee's I-9 to confirm work authorization.