Windows Server Upgrade Technology Project Manager

Windows Server Upgrade Technology Project Manager

Location: Hybrid in London 3 days a week

Contract: rolling 6 month contract (FTC only)

Salary: £75,000-£100,000

Role Purpose

Lead the delivery of a Windows Server upgrade programme, ensuring the server estate remains secure, supported, and compliant with internal security policies and external regulatory requirements. The role is accountable for planning and delivering upgrades of Windows Server platforms across data centre and hybrid environments, minimising risk to business critical applications and services.

Key Responsibilities

• Develop and maintain the project delivery plan for the Windows Server upgrade programme, aligned to Technology strategy, security requirements, and agreed timelines.
• Lead the end to end project management of Windows Server upgrade activities, including estate discovery, upgrade planning, dependency management, testing, cutover, and decommissioning of legacy operating systems.
• Work closely with Infrastructure, Operations, Application Owners, Architecture, and Information Security teams to confirm scope, upgrade approach, and non functional requirements including availability, performance, resilience, and security.
• Coordinate server upgrade and migration activities, ensuring clear runbooks, tested rollback plans, and business approved maintenance windows are in place.
• Ensure risks associated with unsupported operating systems, application compatibility, service availability, and security exposure are identified, mitigated, and actively managed.
• Oversee third party vendors and partners supporting server upgrades or remediation activities, ensuring delivery aligns with agreed scope and quality expectations.
• Maintain project governance artefacts including plans, RAID logs, dependency tracking, and status reporting, escalating risks, issues, and decisions through appropriate Technology governance forums.
• Coordinate testing and validation activities including functional testing, security validation, and operational acceptance prior to service handover.
• Support operational handover to Infrastructure and Operations teams, ensuring documentation, monitoring, and support arrangements are in place.
• Ensure legacy servers are formally decommissioned in line with asset management, security, and data disposal policies.

Required Experience

• Proven IT Project Manager experience delivering infrastructure or platform upgrade programmes in complex enterprise environments.
• Demonstrable experience leading Windows Server upgrade initiatives, including large scale estate remediation or operating system refresh programmes.
• Strong understanding of Windows Server environments, upgrade approaches, and dependencies across applications and infrastructure services.
• Experience coordinating upgrades in environments with business critical and regulated systems.
• Strong stakeholder management skills, with experience working across Infrastructure, Operations, Application teams, Information Security, and third party vendors.
• Experience working within formal IT governance, change control, and service transition frameworks.
• Awareness of security, compliance, and vendor support lifecycle requirements relating to operating system platforms.
• Strong delivery discipline with experience producing and maintaining plans, RAID logs, and senior level reporting.
• Experience in legal industry desirable but not required; other financial or professional services experience preferred.