Director, B2B Sales Capabilities and AI Enablement

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.

Role Summary

The Director, B2B Sales Capabilities and AI Enablement is responsible for defining, building, and scaling the tools, processes, and capabilities that enable our global Sales organization to operate with excellence. This role leads a small team, focused on empowering sellers and sales leaders through streamlined workflows, data-driven processes, effective tools, and adoption of emerging technologies (including AI-enabled solutions).

The Director will work cross-functionally with Sales, Marketing, Product, Finance, and Operations leaders to understand business needs and translate them into scalable, repeatable capabilities that drive productivity, consistency, and revenue outcomes. This is a strategic, high-impact leadership role with visibility across the Commercial organization.

Key Responsibilities

Strategy & Leadership

Develop the long-term vision and roadmap for Sales Capabilities in alignment with Commercial strategy.
Lead and mentor a high-performing team across process design, capability development, tool enablement, and change management.
Serve as a strategic partner for Sales leadership on capability needs, pain points, and investment priorities.

Capabilities & Tooling

Lead the prioritisation, development, and adoption of key sales tools
Evaluates external tooling and industry solutions, benchmarks them against internal capabilities, and develops robust business cases and recommendations. If necessary, leads vendor engagement, contracting, implementation, and successful launch.
Collaborate with cross-functional teams to identify capability gaps and deliver solutions that support global teams at scale.
Champion AI-driven capabilities and ensure they are integrated effectively into sales workflows.

Change Management & Adoption

Drive organizational readiness and enablement for new tools, processes, and ways of working.
Develop communication and rollout plans to ensure high adoption across geographies and sales segments.
Measure adoption, effectiveness, and ROI of capabilities and make data-driven improvements.

Cross-Functional Collaboration

Partner with Product and Tech on capability requirements and prioritization.
Work with Marketing, Operations, and Sales Excellence and Support to ensure consistent execution across the Commercial lifecycle.
Serve as a point of escalation for capability-related issues impacting the field.

Skills & Experience Required

10+ years of experience in Sales Operations, Commercial Operations, Revenue Operations, or related functions.
5+ years in a leadership role managing teams across process, tooling, or capability development.
Proven track record designing and scaling complex sales processes in a global organization.
Deep expertise in Sales technology (CRM, automation tools, enablement platforms; Salesforce expertise strongly preferred).
Experience implementing or integrating AI-powered capabilities or automation initiatives.
Strong stakeholder management skills with the ability to influence senior leaders.
Exceptional communication, strategic thinking, and project leadership abilities.
Comfortable navigating ambiguity and building structure in evolving business environments.

Preferred Qualifications

Experience in a large, matrixed technology or travel industry organization.
Experience building capabilities for both enterprise and SMB sales motions.
Background in change management, continuous improvement, or process excellence frameworks.

Global team leadership experience

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, religion, gender, sexual orientation, national origin, disability or age.