Head of Learning & Culture, Experience Design

Expedia • San Jose, CA

9d

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. The Opportunity At Expedia Group, our goal is to build one of the strongest Experience Design organizations in the industry—spanning product design, content design, research, design operations, and customer advocacy. As we enter the next phase of AI-driven product development, we are investing deeply in how our teams learn, connect, and evolve together. The Head of Learning & Culture for Experience Design will be responsible for defining and scaling a cohesive learning and culture strategy that supports a modern, AI-fluent, globally connected design organization. This role sits at the intersection of learning strategy, cultural activation, and industry engagement, and will work closely with Experience Design leadership, Learning & Development, Events, and Internal Communications. This is a foundational role for the next chapter of the experience design organization—focused on building durable systems, programs, and rituals that help teams do their best work and feel connected while doing it.

Requirements

• Senior experience leading learning, culture, or community programs within design, technology, or creative organizations.
• Strong understanding of design, research, and content disciplines and how they develop skills and craft over time.
• Fluency in AI tools, workflows, or emerging technology trends, or a demonstrated ability to build learning programs around them.
• Proven ability to build programs from scratch, scale them globally, and adapt as organizations evolve.
• Exceptional cross-functional collaborator, comfortable working with executives, AI teams, L&D, Events, and Comms.
• Strong cultural sensibility and taste, with a pulse on the design and creative industry.
• Highly organized, proactive, and comfortable operating in ambiguity.
• Global mindset and experience working across regions and time zones.
• Bachelor’s degree in Design, Human-Centered Design, Learning & Development, Organizational Psychology, Communications, or a related field; OR equivalent professional experience.
• 10+ years of experience inside product, design, or creative organizations— with demonstrable ownership of learning, culture, creative programming, or design-operations initiatives.
• Experience working directly with senior design leadership (e.g., design VPs, heads of research, content, or design systems) to shape culture, craft development, or organizational rituals.
• Proven ability to build programs from scratch, create structure in high ambiguity, and scale initiatives globally across distributed teams and time zones.
• Demonstrated experience designing and leading AI-fluency or modern‑tooling learning programs for design, research, or content teams (e.g., Figma, prototyping workflows, AI tools).
• Strong fluency with design disciplines (product design, content design, research) and their craft development needs.
• Experience orchestrating internal workshops, learning ecosystems, and multi-modal training programs with external vendors or specialists.
• Proven ability to plan and execute cultural, community, or creative events that connect design teams across locations and strengthen organizational identity.
• Exceptional communication, storytelling, and executive-ready presentation skills for influencing without authority.
• Strong operational and program management capabilities: governance, sequencing, prioritization, vendor management, and resource planning.
• Highly organized, proactive, relationship-driven, and comfortable navigating a fluid, evolving environment.
• Global mindset and experience working across regions.

Nice To Haves

• Advanced degree (Master’s) in Design Management, Organizational Development, Behavioral Science, HCI, Learning Sciences, or a related discipline.
• 12–15+ years experience in design operations, learning strategy, culture-building, or creative leadership within large-scale global tech or design organizations.
• Experience building internal AI‑upskilling programs, including vendor evaluation, tool licensing strategies, curriculum development, and internal capability benchmarking.
• Track record defining and orchestrating external-facing design community activations, cultural events, summit-style experiences, and creative partnership pipelines.
• Proven ability to build playbooks, toolkits, and scalable frameworks that unify global design teams and strengthen culture.
• Strong facilitation skills for large-scale workshops, summits, hackathons, or creative community moments.
• Established network within the design, AI, creative, or cultural ecosystem; able to connect the organization to relevant partners, publications, speakers, and institutions.
• Experience managing creative partners, cultural agencies, educators, or industry collaborators.
• Experience contributing to or managing awards, recognition strategies, conference submissions, or speaking pipelines.
• Demonstrated ability to operate as a high-level individual contributor with a budget, activating internal teams and external partners without relying on direct reports.
• Ability to translate vision into actionable strategy in a fast-evolving environment with high ambiguity.

Responsibilities

• Learning Strategy & AI Upskilling Build and scale a comprehensive learning ecosystem for Experience Design, with a strong emphasis on AI tools, workflows, and modern design practice.
• Define and own a global learning strategy and curriculum for Experience Design, balancing: Self-serve learning (toolkits, playbooks, async resources) Live and event-based learning (workshops, talks, labs, hackathons)
• Partner closely with the AI Experiences team to identify emerging skill needs, tools, and workflows—and translate them into actionable learning programs.
• Coordinate with Learning & Development to align on platforms, frameworks, and delivery, while ensuring content is tailored to design, research, and content disciplines.
• Collaborate with Hackathon and Events teams to design meaningful learning moments tied to product, AI, and innovation milestones.
• Identify, source, and manage external partners, agencies, and educators to support continuous learning and AI fluency.
• Continuously assess learning needs and impact, evolving programs as tools, teams, and expectations change.
• Culture, Community & Creative Exchange Build and sustain a connected, high-craft, and creatively ambitious culture across Expedia Group’s global Experience Design organization.
• Establish and support a site-based activation model, including: Clear roles and expectations for site leads Playbooks and guidance for local community-building and programming
• Design and oversee core cultural and creative cadences that bring teams together, such as: Social and community gatherings Design-led events and meetups Moments tied to product, brand, or company milestones
• Create structured forums for creative exchange and visibility, enabling teams to share work, process, and experimentation across product design, content design, research, and customer advocacy.
• Develop and scale signature internal programs (e.g., talks, showcases, summits) that reinforce craft, curiosity, and shared identity in coordination with the events team.
• Strengthen a sense of belonging and connection across locations, ensuring Experience Design feels cohesive, energized, and culturally distinct at a global scale.
• External Partnerships, Industry Presence & Recognition Connect Experience Design to the broader creative and design ecosystem, strengthening external visibility and inspiration.
• Identify and manage external cultural and creative that bring fresh thinking, inspiration, and dialogue into the organization.
• Develop external-facing event series or collaborations that support creativity, learning, and industry connection.
• Own the awards and recognition strategy for Experience Design: Identify relevant awards and opportunities Lead submission strategy and execution in partnership with teams Partner with Events and Internal Comms to support conference participation, speaking opportunities, and industry engagement across design, research, and content.
• Ensure Experience Design is not only learning internally, but actively contributing to—and learning from—the broader design community.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level