Principal Delivery Enablement

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.

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

Role overview:

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.

Key Job Responsibilities and Duties:

• Align delivery enablement initiatives with overall company strategy and key organizational frameworks to drive velocity and organizational effectiveness.

• Shape and evolve the organizational transformation strategy with executive and BU leadership, translating strategic intent into coherent priorities, choices and measurable outcomes across portfolios and value streams.

• Take ownership for addressing complex organizational challenges that impede flow, customer value, fast feedback or autonomous decision-making, turning them into sustainable progress across organizational boundaries.

• Co-design and implement continuous improvement with BU leadership, adapting interventions to context while maintaining alignment with enterprise strategy and desired outcomes.

• Enable end-to-end portfolio management across the company, with the right tooling configurations, ways of working and data insights.

• Bring the standards, practices and behaviors from tooling data and insights as an integrated solution to the stakeholders on a portfolio level.

• Coach, train and mentor stakeholders up to and including C-level on agile mindset, effective ways of working, systems thinking, leadership behaviors and the decision-making changes required for organizational agility.

• Advise and constructively challenge senior stakeholders on governance, funding, operating models, organizational design and decision rights where these enable or constrain effective delivery, fast feedback and autonomous execution.

• Partner with Agile Coaches, Tooling, Data Insights, ELT and relevant Product, Engineering and corporate-function leaders to connect strategic choices to execution and build sustainable coaching and leadership capability across BUs.

• Facilitate executive and cross-BU offsites, workshops and systemic design activities, including design, governance evolution and operating-model change.

• Establish meaningful executive-level metrics and feedback loops to measure transformation progress, surface organizational impediments and support evidence-based course correction.

• Bring broad market knowledge, relevant experience from large-scale transformations and insight into emerging developments, translating them into practical options for the organization.

• Define and own the vision, strategy, success metrics, and roadmap for the integrated delivery enablement product and service offering.

• Work with strategy, change management, Product, Engineering, and Data functions to translate strategic priorities into practical change and land that change across departments.

• Identify and guide the responsible integration of AI capabilities into the strategy and delivery enablement offerings.

• Establish prioritization principles balancing organizational value, business impact, adoption, product quality, and delivery speed.

Role Qualifications and Requirements:

• Proven executive coaching and facilitation across agile ways of working, portfolio management and cultural transformation.

• Strong grounding in agile and lean, systems and complexity thinking, organizational change, and scaled approaches such as SAFe, LeSS or Flight Levels—applied pragmatically.

• Expertise in workforce, talent and skills strategy; organization design; and product or platform strategy, including integrated offerings across organizational boundaries.

• Experience shaping portfolio planning, value streams, Team Topologies, OKRs, cross-functional coordination, and governance, funding, operating models and decision rights that enable fast feedback and autonomous delivery.

• Able to synthesize diverse perspectives into clear executive choices; influence across business units without authority; and constructively challenge assumptions that undermine desired outcomes.

• Skilled in adapting coaching, consulting, learning and change interventions for executive, portfolio, business-unit and enterprise contexts, partnering with strategy and delivery teams to support adoption.

• Data-fluent: defines success measures, interprets qualitative and quantitative evidence, and makes sound decisions amid ambiguity; understands where AI can add value in strategy and delivery.

• Broad awareness of market developments in product operating models, organization design and technology-enabled collaboration.

Advantageous:

• Background in Product, Engineering or Organizational Design.

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.