IT Systems & Security Technical Lead

We’re looking for a IT Systems  & Security Technical Lead

Based in our Bermuda office and reporting to the US-based Manager, IT Support, you will provide advanced onsite and remote support as part of a global team. This role goes beyond traditional L1/L2 support, with a focus on endpoint management, vulnerability and patch remediation, image engineering, automation, and complex escalations.

Hamilton Re is our Bermuda insurer underwriting property, casualty and specialty insurance and reinsurance on a global basis.

What you will do

Frontline & escalation support

• Act as the senior Bermuda escalation point for complex endpoint, OS, AD/Entra, GPO, virtual desktop, and application packaging issues, including root-cause analysis.
• Share rotating dispatcher responsibilities, triage incidents, maintain ticket quality and SLAs, and identify recurring issues that can be engineered out of the queue.
• Provide visible, customer-focused support to Bermuda colleagues and mentor junior support staff as needed.
  

Endpoint engineering & lifecycle

• Own and improve Windows 10/11 endpoint build, image, and deployment processes, including Autopilot, Intune, MDT/WDS, ADK, and golden image maintenance where applicable.
• Package, deploy, and maintain standard and proprietary applications via Intune and/or MECM/SCCM, including silent installs, detection methods, and compliance baselines.
• Support and harden Citrix and/or VMware Horizon virtual desktop environments, including profile management, image updates, and performance/security remediation.
• Manage device lifecycle activities from provisioning and deployment through secure decommissioning and asset reconciliation.

Vulnerability & patch management (in partnership with InfoSec)

• Partner with InfoSec to remediate vulnerabilities and manage patching for Bermuda endpoints and supporting infrastructure using a risk-based approach.
• Operate vulnerability and endpoint security tools such as Qualys VMDR/CSAM and Microsoft Defender for scanning, discovery, inventory, and shadow IT detection.
• Resolve root causes of recurring vulnerabilities, including misconfigured GPOs, broken packages, image drift, and automation failures.
• Track local end-of-life/end-of-support software and hardware and feed remediation plans into the global program.

Automation, scripting & engineering

• Build and maintain PowerShell automations for provisioning, configuration, patching, compliance reporting, remediation, and routine support tasks.
• Design and deploy GPOs and Intune configuration/compliance policies to enforce desktop security baselines and standardize the end-user environment.
• Reduce service requests through process improvement, user enablement, documentation, and automation.

Infrastructure & collaboration

• Support network patching, switch/AP upgrades, and structured cabling activities in the Bermuda office.
• Administer Microsoft 365, Entra ID (Azure AD), Active Directory, Exchange Online, SharePoint, and Intune at an advanced administrator level.
• Collaborate with InfoSec, IT Operations, and global Endpoint Engineering on DR exercises, M365 changes, security tooling, and compliance initiatives.
• Maintain accurate IT documentation, asset records, runbooks, knowledge articles, and CCB-aligned change records.

What you require for the role

• Progressive IT experience, ideally including endpoint engineering, systems administration, or vulnerability/patch management
• Strong hands-on expertise with Windows 10/11, desktop security hardening, office applications, and user hardware
• Advanced administration of Microsoft 365, Entra ID, Active Directory, Group Policy, Intune, and Exchange Online
• Experience with endpoint management, vulnerability, and patching tools such as Intune, MECM/SCCM, Qualys, Microsoft Defender, or WSUS
• Working-to-proficient PowerShell scripting for automation, reporting, and remediation
• Solid grasp of SLAs, ticket management, and incident management disciplines
• Ability to provide on-site and remote support to a globally distributed user base
• Excellent written and verbal communication skills, with the ability to support colleagues at all levels, including senior leadership and auditors

Highly desirable

• Experience with Autopilot, zero-touch deployment, golden image engineering, virtual desktop environments, and endpoint security tooling
• Experience in regulated environments, ideally financial services or re/insurance, and supporting audits such as SOX, ISO 27001, DORA, or NYDFS
• Exposure to change management frameworks, CCB processes, IT asset management, network fundamentals, or SharePoint Online administration

What you can expect from us

We offer a vibrant, entrepreneurial, and collaborative culture guided by our values: Be Smart, Be Sensible, Be Open and Be More.

We know if we welcome and respect differences, we’ll attract and retain talent that brings a valuable diversity of perspectives and experience. We want all our colleagues to feel that they can bring their whole selves to work at Hamilton and know that they can be part of building a great company.

In Good Company

Hamilton (NYSE: HG) underwrites specialty insurance and reinsurance risks on a global basis through its wholly owned subsidiaries. Its three underwriting platforms: Hamilton Global Specialty, Hamilton Select and Hamilton Re, each with dedicated and experienced leadership, provide access to diversified and profitable business around the world.

Headquartered in Bermuda, Hamilton has over 600 employees with key underwriting operations in London, Bermuda, the US and Dublin. We work collaboratively, we share a passion for the service and results we deliver, and we know that what we do each day is meaningful – to our customers and our business. We believe we are ‘In good company.’ with everyone we interact with.