Principal Delivery Enablement - Strategy & Transformation

Role Description

About Us: At Booking.com, data drives our decisions. Technology is at our core. And innovation is everywhere. But our company is more than datasets, lines of code or A/B tests. We’re the thrill of the first night in a new place. The excitement of the next morning. The friends you encounter. The journeys you take. The sights you see. And the memories you make. Through our products, partners and people, we make it easier for everyone to experience the world.

About our team:

Delivery Enablement works in close partnership with teams across People, Tech Enablement, and the wider business. Depending on the needs of each initiative, this includes collaboration across organisational effectiveness, change, HR transformation, leadership and culture, digital HR, talent and skills, and relevant business functions to support the Together initiative. Together, these perspectives connect business strategy, organisational performance and the experience of our people

As a Principal in Delivery Enablement, you shape and lead an integrated transformation and delivery enablement offering that helps teams, portfolios, and departments turn strategic priorities into effective, measurable delivery. You bring together complementary ways of working, technology and data products, agile coaching, and delivery services into a coherent experience across the organization. Partnering closely with business units, executive leadership, strategy, and change management functions, you turn strategic intent into sustainable improvement, coach stakeholders up to C-level, and use foresight to assess AI opportunities for responsible integration into delivery offerings.

Role Overview:

As Senior Manager of Delivery Enablement at Booking.com, you lead a cross-functional track that partners across the company to shape how our workforce, Agile ways of working, operational tooling, and capabilities evolve in line with the Together 2027 narrative.

Our main focus is to enable improving our velocity as a company, with the delivery enablement teams actively driving this across the organisation.

You manage functional leads and their teams across key tracks—including Agile, Jira and tooling, and Data—setting clear direction and empowering them to support teams across Booking.com. You turn business goals into practical priorities for the team, providing guidance while giving leaders the autonomy they need to deliver the right solutions.

Working across strategy, organization design, workforce planning, talent, and change, you turn complex challenges into clear, practical, and people-centered solutions. You connect business goals with the experience of our people to drive lasting improvements in company velocity.

Key Job Responsibilities and Duties:

Strategy, delivery enablement and organisational effectiveness

• Translate business strategy and the Together strategy into a coherent Delivery Enablement direction, defining priorities and outcomes for the department.

• Advise senior stakeholders on organisation design, the Agile operating model, workforce planning, talent strategy and skills-based approaches.

• Apply systems thinking to understand complex, multi-faceted organisational challenges, their dependencies and their impact across the business.

• Anticipate how AI, automation and other emerging technologies may affect the workforce, organisational structures and future skills needs; help leaders translate those implications into considered action.

• Build alignment on strategy and represent the department’s work clearly across People, Technology and business leadership.

Transformation delivery and outcomes

• Lead complex people and workforce transformation initiatives from assessment and strategy through design, implementation and sustained adoption.

• Establish and maintain plans, roadmaps, governance, measures, resources and stakeholder engagement for the department’s portfolio of work.

• Set clear objectives and success measures with partners; use evidence, relevant indicators and feedback to assess progress, surface risks and adapt plans.

• Identify dependencies and risks early, resolve blockers across initiatives and coordinate delivery so that connected work contributes to shared outcomes.

• Define fit-for-purpose ways of working that help teams deliver efficiently while maintaining quality and accountability.

• Facilitate strategic workshops and leadership discussions to build alignment on transformation goals, choices and priorities.

Workforce and capability development

• Develop approaches to build a future-ready workforce through skills development, talent deployment, reskilling, upskilling and capability building.

• Connect workforce and talent insights with business priorities to identify capability gaps, opportunities and practical actions.

• Contribute to the continued development of Booking.com’s people and workforce transformation capabilities, practices and Agile ways of working.

• Balance pace and business priorities with a thoughtful, human-centred approach to change and adoption.

People leadership and community contribution

• Lead the horizontal Delivery Enablement department, providing people leadership and direction for practice leads and their direct reports across key operational tracks, including Agile, Jira, and Data.

• Coach and develop this leadership group and its teams, supporting strong craft, individual growth, collaboration, accountability and high performance.

• Create clarity of direction while enabling leaders and teams to exercise appropriate autonomy and maximise their contribution.

• Build a strong transformation community by sharing practices, developing learning and contributing to recruitment, mentoring and capability-building activities where relevant.

Partnership and stakeholder leadership

• Build trusted partnerships across People teams and the wider business, learning stakeholders’ needs and plans and identifying opportunities to connect related initiatives.

• Manage expectations through timely, concise and clear progress updates, adapted to the audience and medium.

• Influence confidently at senior levels, bringing multidisciplinary groups together around shared outcomes and constructive decisions.

• Depending on initiative needs, partner across organisational effectiveness, change, HR transformation, leadership and culture, digital HR, talent and skills, and relevant business functions.

Role Qualifications and Requirements:

• You will bring a strategic perspective and a strong track record of delivering transformation, with deep expertise in organization design, workforce and talent strategy, and change. You move confidently between setting direction and hands-on execution, turning complex business challenges into clear choices and practical action plans.

• As an experienced people leader, you develop leaders and teams, set a clear direction for your portfolio, and bring people together around shared goals. You balance enterprise priorities with team ownership and accountability.

• Ground decisions in data, evidence and stakeholder insight. You work effectively with specialists, make sound calls when information is incomplete, and define meaningful measures that connect transformation efforts to business outcomes.

• Build trusted relationships across the organization and communicate with clarity at every level, from delivery teams to senior leaders. You combine pace with a human-centered approach and bring a practical perspective on AI, digital transformation and the future of work—helping leaders navigate change and build adaptable teams.

Benefits & Perks - Global Impact, Personal Relevance:

Booking.com’s Total Rewards Philosophy is not only about compensation but also about benefits. We offer a competitive compensation and benefits package, as well unique-to-Booking.com benefits which include:

• Annual paid time off and generous paid leave scheme including: parent, grandparent, bereavement, and care leave

• Hybrid working including flexible working arrangements, and up to 20 days per year working from abroad (home country)

• Industry leading product discounts - up to 1400 per year - for yourself, including automatic Genius Level 3 status and Booking.com wallet credit

Diversity, Equity and Inclusion (DEI) at Booking.com:

Diversity, Equity & Inclusion have been a core part of our company culture since day one. This ongoing journey starts with our very own employees, who represent over 140 nationalities and a wide range of ethnic and social backgrounds, genders and sexual orientations.

Take it from our Chief People Officer, Paulo Pisano: “At Booking.com, the diversity of our people doesn’t just build an outstanding workplace, it also creates a better and more inclusive travel experience for everyone. Inclusion is at the heart of everything we do. It’s a place where you can make your mark and have a real impact in travel and tech.”

We ensure that colleagues with disabilities are provided the adjustments and tools they need to participate in the job application and interview process, to perform crucial job functions, and to receive other benefits and privileges of employment.

Application Process:

This role does not come with relocation assistance.

• Application and CV Review

• Recruitment Phone Screen

• Business Interview 1

• Business Interview 2

• FIT Interview

• Hiring Decision

Let’s go places together: How we Hire

Booking.com is proud to be an equal opportunity workplace and is an affirmative action employer. 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. We strive to move well beyond traditional equal opportunity and work to create an environment that allows everyone to thrive.