Head of Tech Delivery and Assurance

About Booking.com

Established in 1996 in Amsterdam, Booking.com has grown from a small Dutch start-up to one of the largest ecommerce companies in the world. Booking.com is the largest business within Booking Holdings (NASDAQ: BKNG) and accounts for the vast majority of Booking Holdings’ total revenue. Booking Holdings is a leading Fortune 500 e-commerce conglomerate with a market cap of roughly $75 billion (2022). Booking.com currently employs approximately 10,000 employees in 120+ offices in 70 countries worldwide.

With a mission to make it easier for everyone to experience the world, Booking.com invests in digital technology that helps take the friction out of travel. Booking.com connects travelers with the world’s largest selection of incredible places to stay, including everything from apartments, vacation homes, and family-run B&Bs to 5-star luxury resorts and even tree houses. In addition to accommodations, customers can book flights to over 4,500 destinations, book curated attractions and experiences in over 2,300 cities and reserve rental cars in over 140 countries. Via the customer experience team, customers can reach Booking.com 24/7 for assistance and support in over 44 languages, any time of the day or night.

At Booking.com, we are all involved in making hundreds of decisions every day. The decisions we make are a reflection of our Values - they reflect what is important to us, both as individuals and as an organisation.

When Values are made explicit, they provide clarity on what “good” looks like. And when they are shared, they build unity in a group. They build culture.

• Think customer first. We obsess about adding value for our customers - guests, partners, colleagues - to make it easier for everyone to experience the world.
• Own it. We deliver on our promises, make informed decisions and prioritize to get the important things done today.
• Learn forever. We are resilient, take time to reflect, and seek to learn – from colleagues, from the outside world and from our failures.
• Succeed together. We celebrate team success, through making connections, building trust and valuing the diverse perspectives of others.
• Do the right thing. We get the right results the right way. For each other, our communities and the world around us.

About The Role

The Head of Tech Delivery and Assurance is the execution backbone of People Tech. This is a transversal leadership role responsible for ensuring that every approved initiative in the People Tech portfolio is delivered on time, within scope, and with full visibility — across all five departments and almost 60 internal team members.

This role does not manage a single department — it manages the portfolio. It owns delivery discipline, governance standards, financial controls , and the reporting framework that keeps the Director and leadership informed at all times.

It operates without functional ownership of any single domain — making cross-team influence, process rigour, and delivery credibility the primary tools of this role.

Key Responsibilities

Portfolio Delivery & Execution

• Own the end-to-end delivery of the People Tech approved portfolio across all departments.
• Assign initiatives to the right teams with clear timelines, owners, and success criteria.
• Run weekly delivery cadence: status tracking, risk identification, blocker escalation.
• Consolidate portfolio status and present monthly to the Director with clear RAG reporting.
• Ensure the 40/40/20 capacity model (Tech-driven / Business-driven / Strategy-driven) is respected across active initiatives.

Governance, Controls & Compliance

• Own the governance framework for all People Tech projects — templates, stage gates, escalation paths.
• Manage purchase orders, contracts, and vendor governance in coordination with Finance and Procurement.
• Ensure all significant investments are supported by solid business cases per agreed standards.
• Maintain risk and audit readiness across the function at all times.

Financial Management

• Own the People Tech portfolio budget tracking — actuals vs. plan, forecast accuracy, and variance reporting.
• Work closely with Finance to ensure budget best practices are met.
• Manage vendor and managed services spend within agreed thresholds.

People Leadership

• Lead and develop the Tech Office team including TPMs , the Service Assurance Manager. And the testing service.
• Build capability in project and programme management across the broader People Tech team.
• Foster a culture of delivery accountability, transparency, and continuous improvement.

Stakeholder & Cross-functional Engagement

• Act as the primary interface between People Tech delivery and internal stakeholders (Finance, Procurement, Risk & Compliance, Legal).
• Collaborate closely with Tech Advisory to ensure smooth hand-off from approved brief to execution.
• Communicate proactively with department Heads on portfolio priorities, capacity constraints, and delivery risks.

What You Will Own

Portfolio status

Weekly delivery tracking across all active initiatives

Governance framework

Templates, stage gates, escalation paths, audit readiness

Financial controls

Budget tracking, POs, contracts.

Vendor management

Oversight of managed services and external partners

Reporting

Monthly portfolio report to Director; quarterly to HR leadership

Capacity model

Ensuring 40/40/20 distribution is maintained

What This Role Does NOT Own

Technical solution design (→ Technical Solutions / Digital Solutions)

• Business demand intake (→ Tech Advisory)
• Strategic roadmap (→ Senior Strategy Manager)
• Platform operations or incident management (→ Platform & Product Ops)
• Budget approval (→ Director)

Experience

What We Are Looking For

• 12+ years of experience in technology programme management, delivery governance, or PMO leadership.
• Proven track record managing complex, multi-team portfolios in a matrixed organisation.
• Experience in HR Tech, People Systems, or enterprise SaaS environments strongly preferred.
• Background in financial management, PO oversight, and vendor governance.
• Familiarity with SOX compliance and risk & control frameworks.

Skills

• Mastery in portfolio and programme management — able to hold a complex portfolio together without owning any single domain.
• Strong stakeholder management — comfortable engaging at Director and ELT level across multiple functions.
• Financial acumen — can read a budget, identify variances, and drive corrective action.
• Process discipline — brings rigour without bureaucracy; knows when to enforce and when to flex.
• People leadership — builds delivery capability in others, not just in themselves.
• Excellent communication — translates delivery complexity into clear, actionable executive reporting.

Mindset

• Execution-first — gets things done and holds others accountable without being a blocker.
• Transparent by default — proactively surfaces risks before they escalate.
• Collaborative — the PMO function only works if department Heads trust and respect it.
• Comfortable with ambiguity — this is a new function; the person in this role will help shape it.

Why This Role

People Tech is one of the most strategically visible technology functions in the organisation — operating at the intersection of AI, HR transformation, and enterprise-wide digital change. The Head of Tech Delivery and Assurance will play a central role in ensuring that ambition translates into delivery.

This is a high-visibility role that reports directly to the Director and interfaces with HR leadership, Finance, and the broader Enterprise Domain. It is also a function being built — the person who joins will have genuine influence over how the PMO operates, not just inherit a fixed model.

Pre-Employment Screening

If your application is successful, your personal data may be used for a pre-employment screening check by a third party as permitted by applicable law. Depending on the vacancy and applicable law, a pre-employment screening may include employment history, education and other information (such as media information) that may be necessary for determining your qualifications and suitability for the position.