Principal Delivery Enablement: Transformation & AI Strategy

Booking Holdings, Inc.; Amsterdam; Hybrid; EUR 130,000 - 180,000; Full time

Benefits offered by this job

Hybrid working

Annual leave and flexible time off

Discounts onBooking.com products

Job summary

Booking.com is seeking a Principal in Delivery Enablement to shape and lead an integrated transformation offering that turns strategic priorities into measurable delivery. You will unite coaching, data, and technology to turn strategic priorities into measurable delivery, partnering with executives and business units to drive rapid, sustainable improvement.

You will collaborate with Agile Coaches, Product, Engineering and Strategy, establish executive metrics, design operating models, and guide

Qualifications

• 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.

Responsibilities

• 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.

Skills

Executive coaching

Agile coaching

Portfolio management

Systems thinking

Leadership

Education

Bachelor's degree in a relevant field

Tools

SAFe

LeSS

Flight Levels

Job description

Booking.com is seeking a Principal in Delivery Enablement to shape and lead an integrated transformation offering that turns strategic priorities into measurable delivery. You will unite coaching, data, and technology to turn strategic priorities into measurable delivery, partnering with executives and business units to drive rapid, sustainable improvement.

You will collaborate with Agile Coaches, Product, Engineering and Strategy, establish executive metrics, design operating models, and guide