[Hiring] Cloud Windows Infrastructure Engineer @Gresham

Role Description

As Senior Windows Infrastructure Engineer, you are the technical anchor for the Windows estate that powers Gresham's managed services platform — a multi-client environment hosted on AWS. The work is grounded in deep Windows Server operations:

• Active Directory
• IIS
• Hybrid identity
• Group Policy
• PowerShell
• Certificate services
• The wider Microsoft ecosystem

This is a 100% individual contributor role. You will not manage or lead a team. You will own complex incidents end-to-end, set technical standards by example, and act as the senior escalation point for the Cloud Support function. You will be working US hours so please only apply if you are able to do so.

Role Responsibilities

• Lead resolution of complex Windows Server incidents across multi-client, AWS-hosted environments — from triage to root cause to remediation.
• Administer and harden Windows Server 2019/2022/2025:
• Active Directory (forest/domain design, replication, FSMO, GPOs, trusts)
• DNS
• DHCP
• IIS
• WSUS
• AD CS
• File & print services
• Operate hybrid identity: AD on-prem ↔ AWS Managed Microsoft AD, federation with Entra ID (Azure AD) / AD FS, SAML / OIDC / OAuth, Kerberos, MFA.
• Author and maintain PowerShell automation: bulk administration, scheduled tasks, configuration drift correction, reporting, and DSC where appropriate.
• Operate the AWS hosting layer for Windows workloads: EC2, EBS, VPC, IAM, Route 53, CloudWatch, Systems Manager (Patch Manager, Session Manager, Run Command), Backup, Directory Service.
• Manage IIS in depth: sites, application pools, bindings, ARR / URL Rewrite, SSL/TLS, failed request tracing, and performance tuning.
• Drive observability of the Windows estate: event log strategy, performance baselines, CloudWatch metrics & alarms, Grafana dashboards.
• Author runbooks, SOPs, and knowledge base articles to codify operational standards.
• Participate in ITIL incident, problem, and change management; act as senior on-call escalation.

Qualifications

• 7+ years operating Windows Server in production, with deep hands-on experience on Windows Server 2019 and above.
• Active Directory at depth: forest/domain design, replication, FSMO roles, trusts, sites & services, schema, tombstone & recovery.
• Group Policy at scale: design, troubleshooting (RSoP, gpresult), security baselines, WMI filtering.
• IIS at depth: site & app pool configuration, ARR, URL Rewrite, SSL/TLS, failed request tracing, performance tuning.
• DNS, DHCP, WSUS, and Active Directory Certificate Services (AD CS) — real operational experience.
• Advanced PowerShell: scripting, modules, remoting, error handling, automation patterns, DSC familiarity.
• Windows patching at scale: planning, deployment, rollback, and troubleshooting in regulated environments.
• Windows performance troubleshooting: PerfMon, ETW, memory dump analysis, IIS request diagnostics.
• Hybrid identity: AD on-prem ↔ cloud, Entra ID (Azure AD) Connect / federation, AD FS.
• SAML 2.0, OIDC, OAuth 2.0, Kerberos, LDAP, MFA — practical implementation and troubleshooting.
• Certificate management and PKI in enterprise Windows environments.
• Day-to-day comfort operating Windows workloads in AWS: EC2, EBS, VPC, IAM, Route 53, CloudWatch.
• AWS Systems Manager for Windows fleet management: Patch Manager, Session Manager, Run Command, State Manager, Parameter Store.
• AWS Directory Service / Managed Microsoft AD / AD Connector.

Requirements

• Strong ITIL grounding: incident, problem, change, and service lifecycle management.
• Prior experience in an MSP or shared-services environment — multiple client estates managed under SLA.
• Advanced / fluent professional English, written and spoken.
• Reliable, distraction-free home office with stable broadband (100 Mbps+ recommended), reliable power, and a professional video setup.
• Ability to work New York-aligned hours consistently, with the same presence and responsiveness as an office-based colleague.

Working Hours, Remote Setup & Engagement

• This role is 100% remote and 100% individual contributor.
• You will operate aligned to New York business hours (08:30–17:30 ET).
• Typical Brazil hours: 09:30–18:30 BRT during EDT (US summer) and 10:30–19:30 BRT during EST (US winter).
• Quiet, ergonomic workspace with stable broadband (100 Mbps+ recommended), reliable power, and a professional video / audio setup.
• Participation in a senior escalation rota for major incidents — compensated in line with policy.

Equal Opportunities Statement

At Gresham, we are committed to building a diverse and inclusive workforce that reflects the communities we serve. We actively encourage applications from individuals of all backgrounds and are dedicated to providing a workplace where everyone feels valued, respected and supported.