Windows SysAdmin Lead

We seek a highly skilled Windows Administrator to join the Gresham Cloud Services team as a 100% individual contributor.

The ideal candidate will have extensive experience in managing Microsoft server environments with a solid background in private, hybrid cloud, or on-premises systems.

This role presents a unique opportunity to develop expertise in public cloud platforms (e.g. AWS, OCI, Azure) as you transition from traditional sysadmin responsibilities into a broader, cloud-centric role.
You will be instrumental in maintaining, modernising, and improving our Windows server environments across multiple hosted facilities, including Rackspace, AWS, and Azure, to support the deployment of Gresham’s diverse portfolio of products.

Your hands-on experience will be vital in introducing and implementing a well-organised approach in supporting a wide variety of deployments.

Key Responsibilities

 • Execute the deployment, monitoring, and ongoing support of all Windows Server environments. Maintain and enhance the performance of Microsoft-related technologies, including Active Directory, Cluster Management, DNS, DHCP, SSO, and other services.
 • Collaborate with fellow Engineers and product teams to validate, modernise, and enhance systems and automated processes.
 • Drive initiatives to adopt public cloud technologies, facilitating a smooth transition from private/hybrid cloud infrastructures.
 • Develop and support scripts and automation tools using PowerShell.
 • Work closely with the Information Security team to introduce, maintain, or improve security measures.
 • Provide technical guidance and share knowledge regarding cloud services and features across teams.
 • Contribute to the modernisation and supporting multiple cloud environments hosted in various private cloud facilities.

Attributes

 • Self-Motivated and Autonomous – Capable of working independently while maintaining a collaborative approach.
 • Excellent Communication Skills – Strong verbal and written communication abilities.
 • Enthusiastic and Judicious – Demonstrates passion, sound judgement, and effective communication.
 • Technologically Curious – Shows a keen interest in new technologies and continuous learning.
 • Pragmatic Approach – Adopts practical solutions to complex challenges.
 • Senior-Level Execution – Demonstrates expertise in efficiently managing complex tasks with minimal supervision.

Key Skills and Experience

Essential:
• Proven experience in Windows Administration and managing Microsoft server environments.
• In-depth knowledge of Active Directory Administration, DNS, DHCP, and related Microsoft services.
• Hands-on expertise in PowerShell scripting and automation.
• Experience working within private, hybrid cloud, or on-premises infrastructures.
• Familiarity with tools such as Jenkins, patch management systems, SQL Server, and cluster management.
• Understanding of subnets, routing and network fundamentals.

Desirable:
• Keen interest and emerging experience in transitioning to public cloud platforms (e.g. Microsoft Azure).
• Knowledge of Infrastructure-as-Code tools such as Terraform and Ansible.
• Exposure to OpenStack, AWS, SSO configuration skills, and Keycloak.
• Experience in database programming and additional scripting capabilities

Reporting Structure / Working Hours
• Reports directly to the Head of Cloud Services.
• Working hours: US Eastern 08:30 – 17:30

If you are a well-versed Windows engineer with a passion for cloud technologies and a desire to evolve from private or hybrid cloud environments to public cloud expertise, we would be delighted to hear from you.