OS / Infrastructure Administrator Lead

This is a remote position.

OS / Infrastructure Administrator Lead

VMware  ·  Hyper-V  ·  Windows Server  ·  Backup & Recovery  ·  AWS Cloud

We are seeking an experienced and technically hands-on OS / Infrastructure Administrator Lead to join our IT operations team. The successful candidate will bring 10 to 12 years of experience across virtualization platforms, Windows Server environments, backup and recovery operations, and cloud infrastructure — with a proven track record of leading and delivering complex migration projects end to end.

This role demands a professional who can operate at both the strategic and execution levels: designing migration runbooks and governance frameworks, while simultaneously rolling up their sleeves to perform system upgrades, driver updates, compatibility validations, and hypervisor migrations. The candidate will also contribute to capability building within the team, including Hyper-V administration training.

VMware ESXi Administration & Upgrades

•      Plan, schedule, and execute ESXi host upgrades across development, test, and production environments with minimal business disruption

•      Apply driver updates, firmware patches, and VMware Tools refreshes in accordance with VMware compatibility matrices

•      Conduct thorough post-upgrade host validation including vSphere cluster health checks, datastore integrity, and network connectivity verification

•      Maintain upgrade documentation, change records, and rollback procedures for all ESXi lifecycle activities

•      Monitor ESXi host performance, resource utilisation, and HA/DRS configurations to ensure optimal virtualisation efficiency

VMware to Hyper-V Migration

•      Lead end-to-end migration of virtual machines from VMware vSphere to Microsoft Hyper-V, covering planning, execution, validation, and hypercare

•      Perform VM hardware version upgrades and compatibility assessments prior to migration, ensuring alignment with target Hyper-V environment requirements

•      Execute VMware Tools removal and replacement with Hyper-V Integration Services as part of the migration workflow

•      Develop and maintain detailed migration runbooks covering pre-migration checks, execution steps, rollback procedures, and post-migration validation scripts

•      Conduct compatibility validation of applications, network configurations, and storage mappings after migration to Hyper-V

•      Design and deliver Hyper-V administration training sessions for internal IT team members, building in-house capability and reducing dependency on external support

•      Produce knowledge-transfer documentation covering Hyper-V architecture, VM lifecycle management, checkpoints, and networking configuration

Windows Server Administration & Upgrades

•      Plan and execute in-place upgrades and clean installations of Windows Server operating systems (2016 / 2019 / 2022), including pre-upgrade assessment and compatibility review

•      Manage patch lifecycle for all Windows Server environments ensuring compliance with security and operational baselines

•      Administer Active Directory, DNS, DHCP, Group Policy, and file services in support of enterprise infrastructure

•      Coordinate server decommissions, consolidations, and role migrations as part of infrastructure refresh programmes

•      Maintain server hardening configurations and contribute to security compliance activities

Backup, Recovery & Business Continuity

•      Design, implement, and manage enterprise backup strategies covering physical servers, virtual machines, and cloud workloads

•      Administer backup solutions (e.g. Veeam, Veritas NetBackup, Azure Backup) ensuring scheduled jobs, retention policies, and offsite replication are operational

•      Plan and conduct regular recovery drills, validating RTO and RPO targets across critical systems

•      Respond to and manage recovery scenarios including full server restores, file-level recoveries, and VM rollbacks

•      Maintain backup inventory, reporting dashboards, and escalation procedures for backup failures

Migration Project Leadership

•      Lead infrastructure migration projects as the primary technical authority, from scoping and planning through execution and post-migration support

•      Develop project plans, risk registers, migration runbooks, and stakeholder communication packs

•      Coordinate with application teams, network engineers, security, and business stakeholders to align migration windows and minimise impact

•      Chair migration readiness reviews, cutover planning sessions, and post-migration retrospectives

•      Maintain hands-on delivery participation throughout all project phases — not limited to oversight only

AWS Cloud Infrastructure

•      Provide infrastructure support and operational oversight for AWS environments including EC2, VPC, S3, IAM, CloudWatch, and related services

•      Contribute to hybrid cloud architecture discussions, supporting workload placement decisions across on-premises and AWS

•      Apply AWS best practices for security, cost optimisation, and high availability in line with organisational cloud governance

•      Support cloud migration assessments and lift-and-shift activities where applicable

Core Technical Competencies

Technical Requirements

•      Hands-on proficiency in ESXi upgrade procedures, including SUM/VUM-based upgrades, offline bundle upgrades, and driver/firmware update workflows

•      Demonstrated experience in VMware to Hyper-V migrations at scale, including hardware version upgrades, compatibility validation, and runbook authorship

•      Strong Windows Server administration skills across 2016, 2019, and 2022 — in-place upgrades, role migrations, and security baseline management

•      Proven experience designing and managing enterprise backup solutions with validated recovery testing

•      Working knowledge of AWS core services: EC2, S3, VPC, IAM, CloudWatch, Route 53, and related infrastructure services

•      Experience developing migration runbooks, cutover plans, and post-migration validation checklists

•      Ability to design and deliver technical training material for team capability uplift

Leadership & Soft Skills

•      Proven track record of leading infrastructure migration projects from initiation through to post-migration hypercare

•      Ability to operate as both a technical lead and a hands-on engineer — comfortable owning delivery personally, not only directing others

•      Strong stakeholder communication and documentation skills, capable of producing clear technical and executive-facing artefacts

•      Structured approach to problem-solving under pressure, particularly during migration cutover windows

•      Mentoring and knowledge-transfer experience within IT operations teams