Windows Migration Engineer

Keyloop bridges the gap between dealers, manufacturers, technology suppliers and car buyers.

We empower car dealers and manufacturers to fully embrace digital transformation. How? By creating innovative technology that makes selling cars better for our customers, and buying and owning cars better for theirs.

We use cutting-edge technology to link our clients' systems, departments and sites. We provide an open technology platform that's shaping the industry for the future. We use data to help clients become more efficient, increase profitability and give more customers an amazing experience. Want to be part of it?

Role Overview:

We are seeking an experienced Microsoft Engineer to lead a large-scale migration from Windows Server 2016. This role will focus on designing and developing migration strategies in close collaboration with application owners, as well as validating solutions to ensure compatibility and stability. Key responsibilities include assessing existing 2016 environments, identifying risks and dependencies, creating detailed architecture and migration roadmaps, and developing comprehensive test plans to support a seamless transition.

• Lead and contribute to a large-scale Microsoft Server 2016 migration program across multiple environments.
• Assess existing Windows Server 2016 infrastructure, applications, and dependencies to identify risks, remediation paths, and migration readiness.
• Define and design migration strategies and roadmaps, ensuring minimal disruption to business services.
• Work closely with application owners and SMEs to validate compatibility, stability, and performance of workloads post-migration.
• Develop detailed test plans, migration runbooks, rollback procedures, and technical documentation.
• Perform technical proof-of-concepts (POCs), solution validations, and provide recommendations for migration approaches.
• Collaborate with security teams to ensure migration activities align with corporate security standards and remediate vulnerabilities.
• Provide technical expertise and act as a subject matter authority for Windows Server migrations within hybrid on-prem and cloud environments.
• Support migration execution phases with troubleshooting, root cause analysis, and post-migration validation as required.
• Mentor and provide knowledge transfer to operational support teams to ensure long-term sustainability of the migrated environments.
• Stay current with Microsoft lifecycle, Extended Security Updates (ESUs), and emerging technologies to inform migration planning.

• Strong expertise in Microsoft Windows Server (2012–2019) with a focus on migration planning, design, and validation.
• Hands-on experience with Active Directory, DNS, DHCP, Group Policy, and Certificate Services, including cross-version migrations.
• Proven ability to work with large-scale environments (hundreds or thousands of servers), including dependency mapping and risk assessment.
• Experience in developing and executing migration runbooks, rollback plans, and validation/testing frameworks.
• Knowledge of Microsoft lifecycle management, including Extended Security Updates (ESUs), patching, and compliance considerations.
• Practical understanding of SCCM / Endpoint Configuration Manager and automation tools for system upgrades and configuration deployment.
• Familiarity with hybrid environments (on-premises and cloud, e.g., AWS) and workload migration strategies.
• Awareness of security best practices, endpoint protection, and hardening standards during OS transitions.
• Strong troubleshooting and problem-solving skills, particularly with compatibility and application stability issues during migration.
• Ability to manage multiple concurrent workstreams and collaborate across infrastructure, application, and security teams.
• Desirable knowledge of VMware virtualization platforms and SQL Server basics to support integrated migrations.

Why join us?

We're on a journey to become market leaders in our space – and with that comes some incredible opportunities. Collaborate and learn from industry experts from all over the globe. Work with game-changing products and services. Get the training and support you need to try new things, adapt to quick changes and explore different paths. Join Keyloop and progress your career, your way.

An inclusive environment to thrive

We're committed to fostering an inclusive work environment. One that respects all dimensions of diversity. We promote an inclusive culture within our business, and we celebrate different employees and lifestyles – not just on key days, but every day.

Be rewarded for your efforts

We believe people should be paid based on their performance so our pay and benefits reflect this and are designed to attract the very best talent. We encourage everyone in our organisation to explore opportunities which enable them to grow their career through investment in their development but equally by working in a culture which fosters support and unbridled collaboration.

Keyloop doesn't require academic qualifications for this position. We select based on experience and potential, not credentials.

We are also an equal opportunity employer committed to building a diverse and inclusive workforce. We value diversity and encourage candidates of all backgrounds to apply.