Cloud Migration Project Manager Simulation — Booking.com

The scenario

Booking.com runs almost everything an engineer does day to day through Atlassian. Roughly 22,000 people across Amsterdam, Manchester, Barcelona, Shanghai, Bangalore and seven other offices open Jira to move work and Confluence to write down what they decided. That estate grew the way estates grow — one instance per acquisition, per department, per team that wanted its own workflows — until it reached 8 Jira instances and 12 Confluence instances, each with its own administrators, its own field schemes and its own accumulated fifteen years of history. The estate is now on borrowed time in two different ways at once. Some instances still run Atlassian Server, which stopped receiving security patches in February 2024 and survives inside Booking.com only under a documented risk acceptance signed by Security & Privacy Assurance. The rest run Data Center, where Atlassian ended renewals in March 2026 and every remaining licence now has a fixed expiry. Both roads lead to the same place, and the Technology Investment Board approved €6.4M to walk it: consolidate twenty instances onto Atlassian Cloud Enterprise, pinned to the EU region, with Adaptavist as the migration partner. Your predecessor left a clean inventory and a clean plan. Both are built on the assumption that twenty instances is twenty of the same problem repeated twenty times, that 47 marketplace apps is a procurement exercise, and that a workflow is a thing you can rebuild from a screenshot. Your job is to find out which of those assumptions is false before the migration finds out for you.

What you'll do as the project manager

• →Migrate 8 Jira instances and 12 Confluence instances onto a single Atlassian Cloud Enterprise organisation with all data pinned to the EU region
• →Move approximately 22,000 users onto Atlassian Guard with SAML single sign-on and enforced two-step verification, with no user losing access on a working day
• →Reach a documented disposition for all 47 marketplace apps — migrated, replaced, rebuilt or retired — before the first production wave cuts over
• →Retire every unsupported Server instance before the current Security & Privacy Assurance risk acceptance expires
• →Hold total programme spend within the €6.4M baseline, including the €0.12M contingency

Project management skills you'll build

The challenges you'll navigate

• •Fourteen of the 47 marketplace apps have no cloud equivalent — the disposition for each is unowned as of Day 1 and every option (replace, rebuild, retire) costs either money or a working practice
• •The estate is not uniform: an unknown number of the twenty instances are unsupported Server rather than Data Center, and the two require different migration paths, different tooling and different security handling
• •Release Engineering's custom Jira workflow governs the production release approval that internal audit samples — it does not survive migration in its current form and the rebuild is a six-week parallel workstream nobody has staffed
• •Contingency stands at €0.12M, under 2% of baseline — the predecessor committed to that figure to get the charter through the Technology Investment Board, and any material surprise needs a supplemental
• •Adaptavist's fixed-price statement of work prices the migration of apps that have a cloud equivalent, and is silent on the ones that do not

Technology & stakeholders

You'll manage 7 stakeholders, including Marieke van Dooren (Director, Engineering Ecosystems), Diederik Brakenhoff (Head of Technology PMO), Sander Osterhout (Principal Engineer, Developer Platform), and more.

What you'll walk away with

A verified, shareable record of a completed enterprise project — plus the PMO deliverables you produced along the way (charter, project plan, SteerCo deck, closure document). It's real, demonstrable project management experience you can put on your resume and speak to in interviews.

Frequently asked questions

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